Money Over Everything: Charting Hip Hop’s Cash Flow


In a basement on Lexington Avenue in Brooklyn, DJ Hitman 50 Grand spun the “Impeach the President” break for a young MC he’d met earlier that day. Recorded in 1973 by The Honey Drippers (a group of high school kids from Jamaica, Queens led by southern singer Roy Charles Hammond) in an attempt to capitalize on the Watergate scandal, “Impeach the President” had long since outgrown its novelty and become a crucial part of hip-hop’s musical backbone. The song opens with a supple, lolling beat featuring a snare drum that provides a useful metronome for even the most inexperienced rappers. The breakbeat rose to popularity in the mid-1980s at a time when rappers were experimenting with different types of syncopation in their rhymes and pushing the boundaries of lyrical density. 50 Grand couldn’t have known it then, but the rapper in his basement on that day in 1991 would eventually become known for possessing one of the greatest—if not the greatest—lyrical flows of all time. At that point, though, Cristopher Wallace was a cock-eyed, overweight, low-level crack-dealer—known only for winning a few freestyle rap battles in his Bedford-Stuyvesant neighborhood. He couldn’t even afford to book a studio to cut his own demo tape, but as the breakbeat looped, Wallace unleashed a series of intricate rhymes that would ultimately land him a record deal and set in motion a sequence that would reconstruct the idea of wealth itself in hip-hop music.

Wallace, who took the name “Biggie Smalls” after a gangster character from the 1975 Sidney Portier/Bill Cosby comedy Let’s Do It Again, recorded four songs that day, but it was the one featuring the “Impeach the President” break that 50 Grand began to pass around. That track, “Microphone Murderer,” showcases Biggie’s lyrical prowess, but it is more striking for the unique way he patterns his baritone voice in a heavy, dancehall-like lilt, providing a counter-rhythm that knocks harder than the beat itself. The Honey Drippers’ funky breakbeat makes the track swing, evoking a relaxed confidence in Biggie that helps the 20-year-old sound like an authority figure. Shortly after the recording session, 50 Grand got the demo into the hands of longtime hip-hop advocate Mister Cee, a famous radio personality from the neighborhood. Cee passed “Microphone Murderer” to Matteo Capoluongo, a writer for The Source who, in turn, championed Biggie Smalls in “Unsigned Hype,” a column that spotlighted talented rappers without label deals. Through “Unsigned Hype,” Biggie Smalls caught the attention of a young entrepreneur on the cusp of launching his own label.[1]

By the time 24-year old Sean “Puffy” Combs unveiled Bad Boy Records, he had already achieved a remarkable amount of success within the music industry. Beginning as an intern under Andre Harrell at Uptown Records, he quickly became an executive, shepherding the careers of R&B stars Jodeci and Mary J. Blige along the way. His work with Uptown’s artists helped develop a new aesthetic niche in hip hop-influenced R&B—one which stood in contrast to the popular New Jack Swing of the time by swapping out frenetic bawdiness for mature sultriness. Harrell called the style “hip hop soul.”[2] Like many producers of the time, Puffy also favored the “Impeach the President” drum break, a perfectly emblematic fragment for hip hop soul because it evokes both jazzy elegance and old school boom-bap. Combs’ use of “Impeach the President” on his remix of Jodeci’s “Come and Talk to Me” was a pivot point in the evolution of the Uptown sound. Later—in fact, shortly before getting fired by Harrell in 1993—he used his reworking of Blige’s hit “Real Love” (another song built around that same break) to advertise his forthcoming label, branding it a “Bad Boy Remix” and giving a featured spot to Biggie Smalls, who would eventually become Bad Boy’s flagship artist.

Together, Biggie and Puffy were a study in contrasts. There are recurrent images from their early partnership of Puffy—skinny, muscular, and often shirtless—dancing around his larger friend, like a firefly flitting around a bear. In a 1993 profile in VIBE Magazine, Scott Poulson-Bryant portrays the ascendant Sean Combs as an ambitious ex-model who relishes attention. There’s a story in which young Sean wanted a swimming pool because the white kids that lived across the street from him in Mount Vernon, a suburb of Westchester County in New York, would never invite him over to use theirs. He refused to use the public pool, and begged until his mother relented and took on a second job to be able to afford a pool twice the size of the others in the neighborhood. Elsewhere in the profile, Puffy tells Poulson-Bryant, “Anything I’ve wanted, I can say I got it.”[3]

Like Combs, Christopher Wallace had palpable charisma; unlike Combs, Wallace’s charisma derived from a gravitas that belied his age. Next to the hyperkinetic Puffy, Biggie Smalls came off as laconic; when rapping, however, his relaxed confidence anchored his momentous vocal delivery. He projected assurance and credibility. Wallace had grown up in Bedford-Stuyvesant, or BedStuy, a predominantly black neighborhood that had risen as a cultural counterpart to Harlem during the Great Depression, but had been overrun with street crime by the time Biggie was growing up in the eighties. A story in the biography Unbelievable depicts Christopher begging his mother for a pair of fashionable Timberland boots, and promising to offset the expense by not wearing any other shoes for a year.[4] At twelve years old, Wallace started selling drugs; by seventeen he’d dropped out of high school. He’d racked up arrests on drug and weapons charges well before finding himself recording his demo in 50 Grand’s basement.[5]

The demo tape that landed Biggie Smalls’ deal on Bad Boy Records consisted mostly of fairly straightforward battle raps. In retrospect, two subjects that would go on to define his catalogue were conspicuously absent: He didn’t rhyme about being poor; he didn’t rhyme about getting rich. On his first single for Bad Boy, he rhymes about both. “I made the change from a common thief,” he boasts on “Juicy,” “to up close and personal with Robin Leach.” “Juicy” articulates the change from pre-Bad Boy Christopher Wallace to Bad Boy artist The Notorious B.I.G. (a moniker he took when some copyright issues arose around the name Biggie Smalls). The song depicts Wallace growing up in abject public housing (“a one-room shack”), a child tracking hip hop’s evolution from something that was mocked by mainstream culture (in, for example, Shawn Brown’s “Rappin’ Duke”) to something that became a pop juggernaut in the early 90s. According to the lyrics, now that he’s become a professional rapper, Biggie is able to surround himself with luxuries he’d never even imagined as a kid—women, champagne, diamonds, a personal chauffeur, and so on. Coming at the very beginning of The Notorious B.I.G.’s rap career, “Juicy” was mostly wishful thinking, but it made the leap from poverty to wealth sound as easy as flipping a switch.

The “Juicy” video makes the change in Biggie’s lifestyle even more explicit. There are two Biggies: Christopher Wallace, getting arrested by undercover cops on a BedStuy street corner; and The Notorious B.I.G., hosting a lavish pool party at a mansion. Puffy, already known for obsessively styling Jodeci and Mary J. Blige, presumably also dressed Biggie for the “Juicy” shoot. In the BedStuy scenes, Christopher Wallace wears T-shirts; at the mansion The Notorious B.I.G. is draped in a white leisure suit. The effect each outfit has on Biggie’s appearance is stunning. In BedStuy, he looks awkward in his own body. He is overweight, and the weight doesn’t appear to be in the right places. His face appears doughy. In other words, he looks like a kid that has not yet grown into himself. In his finery, on the other hand, Biggie appears completely at ease as he grooves along to his own music. It is as if he has matured overnight. At the mansion, Biggie looks like a man.

“Juicy,” 1994              

It’s not a stretch to imagine that the pool party was also Puffy’s idea. After all, swimming pools held a special significance for Puffy ever since the white kids across the street in Mount Vernon had denied him access to theirs. Combs, familiar with the language of affluence from his childhood in Westchester County, likely introduced the iconography of wealth to Wallace’s rap lexicon. While Biggie’s debut album, Ready to Die, quickly became known for stunning psychological depths within Biggie’s depictions of his criminal past, references to wealth—specifically, symbols of the white upper class—pop  up throughout the album. It’s easy to imagine Puffy purring about money into Biggie’s ear, because on many Notorious B.I.G. songs, including “Juicy,” you literally hear him whispering brand names like a yogi intoning a series of mantras. Fond of inserting his own voice into his productions as a sort of phantom hype man, Puffy is right there on the backing track of Biggie’s lead single, seductively dropping references to luxury: “bankrolls;” “clothes;” “mansions;” “yachts.”  The tension between struggling with poverty while aspiring to prosperity made Ready to Die an instant classic, and triggered a paradigm shift in hip hop. Today this sort of aspiration is taken for granted as commonplace in rap music. But in many ways, with “Juicy,” Puffy and Biggie created the archetype of the MC who used his rap skills to escape poverty and become not just financially comfortable, but extremely wealthy, bypassing the middle class and cannonballing into the lifestyle of the rich and famous.

“Juicy,” 1994              

In 1992, around the time Biggie and Puffy met, the video for Naughty By Nature’s second single began to circulate on MTV. The three-man group from New Jersey had just scored an inescapable hit with “O.P.P.,” a Jackson 5-sampling meditation on the pleasures of infidelity. Despite the R-rated subject matter, Naughty By Nature and their label Tommy Boy clearly intended for “O.P.P.” to compete in the pop marketplace. “Ghetto Bastard,” which had to be renamed “Everything’s Gonna Be All Right” before its release as a single, was slightly more complicated. Though it followed a structural pattern similar to their hit—this time sampling Boney M’s cover of Bob Marley’s “No Woman No Cry”—the subject matter was far more nihilistic than the titular hook would suggest. Essentially a showcase for Naughty By Nature member Anthony “Treach” Criss, “Ghetto Bastard” detailed his version of growing up in poverty in East Orange.

“This is the story of a drifter,” Treach opens, “who waited for the worst because the best lived ‘cross town. Who never planned on having so didn’t.” He tours the neighborhood, getting held up at gunpoint, stealing cars and “playing hide & seek with a machete.” Treach may have been playing to what he imagined to be a pop audience’s idea of the ghetto—a post-apocalyptic wasteland housing the alien poor—but, because MTV’s rap focus at that time rarely strayed from the territory occupied by artists like MC Hammer and Marky Mark, the depiction of abject poverty felt revelatory. Looking back, “Ghetto Bastard” is the inverse of “Juicy” in nearly all ways. The storytelling feels dire, insular, and self-pitying. The song insists there’s no way out of the projects for Treach (even though we’re clearly watching him on MTV); the path that “Ghetto Bastard” traces away from poverty only leads right back to poverty: “Some life, if you ain’t wear gold, your style was old/ And you got more juice and dope for every bottle sold/ Hell no, I say there’s got to be a better way/ But hey, never gamble any game that you can’t play.”

In the Spring of 1994, a few months before “Juicy” arrived, Queens rapper Nasir Jones released his debut album Illmatic. Nas’ lyrical skill rivaled The Notorious B.I.G., but he stayed away from the particular type of wealth Biggie and Puffy flaunted on “Juicy.” Instead, Illmatic came from the politically conscious strain of rap practiced by artists like Public Enemy and K.R.S.-One, and dealt largely with racial inequality in America—though in a much more nuanced way than the self-defeatist attitude of “Ghetto Bastard.” In fact, the album features a subtler analog to “Ghetto Bastard” called “The World is Yours” on which Nas raps, “I’m the young city bandit, hold myself down single-handed.” Unlike Treach, Nas does find an escape from the poverty cycle he and they each describe, but it’s internal, not economic. The moments he spends composing his rhymes give him a way out. On the song’s hook, Nas repeatedly declares, “I’m out for dead presidents to represent me,” calling attention to the irony old white men pictured on the dollar bills representing social standing within the black community. In early hip hop, from the 1970s to the mid 1990s, money and symbols of wealth like fly clothes, jewelry, and cars represented status, but this status was generally within a closed circuit—a neighborhood or crew. Verses still frequently arose from the lyrical braggadocio and competition from which rap had been born. Status symbols were often flaunted simply as an extension of that braggadocio.

Hip hop famously began at a rent party in Harlem, where DJ Kool Herc premiered “The Merry-Go-Round”—his technique for using two turntables to extend a break—for a packed house of excited dancers. From the beginning, a simple DJ setup could be turned into a source of revenue, but most early raps concentrated on the party side of the equation. In 1982, three years after the birth of recorded hip hop, a scenester named David Parker, who went by the MC name “Busy Bee,” put the idea on record: “To learn to make money just listen to me… Buy two turntables and a microphone, and you will never get the girls to ever leave you alone.” That record, “Making Cash Money,” is a fascinating prelude to “Juicy” in part because of how it later turns on itself, calling money “the root of all evil.” The same theme resurfaced a few years later on Divine Sounds’ “What People Do for the Money,” which follows characters who are baited by the lure of money to dabble in prostitution, robbery, and a series of other common hustles. Meanwhile, Jimmy Spicer’s “Money (Dollar Dollar Bill Y’all)” exhaustively, if superficially, traced America’s cash flow: “It takes money to get interest from the bank/ It takes money for an army to buy a tank/ It takes money to pay for your doctor bill/ And your psychiatrist if you’re acting ill.” Financially focused raps like the ones by Spicer, Divine Sounds, and Busy Bee were scarce during hip hop’s early years, but it’s notable that each of these examples takes a skeptical approach to money—it is a means to an end, a necessary evil, or a temptation; it is not a thing to covet.

By the mid eighties, rap music had achieved tremendous success. Some rappers infiltrated the music industry; others developed independent business models. Both methods proved capable of incubating hip hop artists, but many of those artists were skeptical of depending on financial support and distribution from label heads and A&R men who didn’t understand or have a vested interest in hip hop culture. As professional rappers became more knowledgeable about the business side of music, they began to write lyrics about the dangers and pitfalls of the job. The title track to Eric B. & Rakim’s Paid in Full pedantically lists the duo’s agency, agent, record company, and management before Rakim launches into the sole verse. “Paid in Full”—the origin of the phrase “dead presidents”—depicts the MC discovering he is broke, then cycling through ways to make money (robbery, a 9 to 5 job) before deciding that making music is the answer. As rapping became a legitimate career choice, being a professional rapper became a common topic in the music. The duo of EPMD built an entire discography upon the theme of hip hop as a business; even their name is an acronym for Eric and Parrish Making Dollars. As rapping became more profitable, many artists inevitably discovered that labels would freely take advantage of their business naiveté. Artists began to lyrically manifest paranoia and mistrust of those around them, whether peers or executives. On “Ring Ring Ring,” the members of De La Soul lament the overwhelming amount of hangers-on that try to pass them a demo tape as a way to break into the rap trade, while A Tribe Called Quest’s “Check the Rhyme” sentimentalizes the time before the group had a label. “Industry rule number four thousand eighty,” Tribe’s MC Q-Tip spells out at one point, “record company people are shady.”

“Paid in Full,” 1987              

The record industry raps provide an interesting parallel to the other ways hip hop depicts making income, from the hustles described in “What People Do for the Money” to Rakim considering a nine-to-five job to Biggie Smalls selling crack cocaine out of his one-room shack. All are forms of commerce, legal or otherwise, and all are portrayed as having similar paths to solvency. In its first couple decades, rap was a consistent promotor of the American ethos that posits hard work as intrinsic to moneymaking, regardless of whether that hard work is criminal or legitimate. A rapper’s mistrust of record executives may feel emotionally different than, say, a drug dealer’s anxiety, but there is a commonality in being in business for one’s self. When a professional artist raps about his dealings in any sort of business, the residue of American capitalism is always present. Each transaction has an unseen ripple of consequences.

By 1993, some professional rappers and hip hop producers had flipped that mistrust of the record industry into a productive entrepreneurial instinct. Staten Island’s Robert Diggs secured a landmark record deal for a sprawling collective of artists made up of friends and family members called the Wu-Tang Clan well before they’d even released their first album. The nine-man group masterminded by Diggs—who called himself The RZA—had a contract with Loud Records, but a clause allowed for each of the individual members of Wu-Tang to sign as a solo artist on a separate label. Prior to this deal, a label would require each member of group to sign a contract that gave the label proprietary rights to subsequent solo material. But when Wu-Tang’s debut took off thanks to its grimy, hyper-authentic version of New York rap, all nine of the members found themselves with brand new deals—each on a different label. In a 2005 interview with Baltimore radio station 92Q, RZA reflected on the arrangement: “We reinvented the way hip hop was structured,” he said, “Wu Tang was a financial movement… So what do you want to diversify? Your assets.”[6]

One of the Wu-Tang Clan’s better-known songs, and one at the center of their 1993 debut Enter the Wu-Tang Clan: 36 Chambers, is about circumventing the cyclical nature of capitalism. RZA builds “C.R.E.A.M.” around a luscious piano sample from an Isaac Hayes-produced song called “As Long as I’ve Got You” by the Charmels. “As Long as I’ve Got You” follows the “Ain’t No Mountain High Enough” archetype, in which a woman will travel to the ends of the earth and endure countless trials for love. “The world is our playground,” Barbara McCoy sings, “as long as I’ve got you.” RZA’s implication is that the man for whom McCoy yearns could easily be one of our dead presidents. “C.R.E.A.M.” finds Wu-Tang MCs Corey “Raekwon” Woods and Jason “Inspectah Deck” Hunter trading verses about chasing money through street hustles. Inspectah Deck describes his crime and drug use as an outgrowth of depression, ultimately learning to maintain balance with a mix of Protestant work ethic and Buddhist acceptance that life is suffering. Raekwon, addicted to cocaine and weed, pays for his drug-dependency with an escalating series of violent crimes—“running up in gates and doing hits for high stakes… sticking up white boys in ball courts”—until he realizes that he’s playing a zero-sum game. On the chorus, Clifford “Method Man” Smith appropriates Jimmy Spicer’s hook from “Dollar Dollar Bill Y’All” as he spells out the titular acronym: “Cash Rules Everything Around Me.”

From “Getting Cash Money” in 1982 to Rakim’s dead presidents in 1987 to “C.R.E.A.M.” in 1993, cold cash was hip hop’s currency of choice. The most liquid of assets, dollar bills can never be worth more or less than their face value. Similarly, a rapper’s on-record aspirations would often get capped at a lifestyle that was affordable with money on hand, like Treach in “Ghetto Bastard,” who “never planned on having so didn’t.” Raekwon’s verse on “C.R.E.A.M.” ends on a positive note, when he breaks the cycle of poverty and addiction by finding success with the Wu-Tang Clan. He makes $40,000 a week, but his material prizes are telling: replacing his old Polo sweater and driving a Mazda MPV minivan. Compare that with The Notorious B.I.G.’s haul on “Juicy”: multiple condos; diamond earrings for his infant daughter; video game consoles; a fifty-inch television; a “money-green leather sofa;” two cars plus a chauffeured limousine; a $2,000 phone bill (“no need to worry, my accountant handles that”); a mink coat for his no-longer-beleaguered mother; and a social calendar that includes interviews, speaking engagements, and brunches where champagne replaces malt liquor as his beverage of choice. Raekwon’s response to success is to make some pragmatic quality-of-life improvements. Biggie Smalls makes a complete lifestyle overhaul, enthusiastically adopting all the trappings of the upper class like Jay Gatsby audaciously mimicking the old money rich on East Egg. He even approaches something as prosaic as playing video games with the giddiness of an impoverished kid with a candy store gift certificate: “Super Nintendo, Sega Genesis. When I was dead broke, man I couldn’t picture this!”

One thing on The Notorious B.I.G.’s list of acquisitions on “Juicy” stands out as a non-luxury item: “Living life without fear.” In his eyes, personal security is one of the benefits of escaping the drug racket and joining the upper class. While “Juicy” and its follow-up singles portrayed Biggie’s flamboyant new lifestyle, tales of his days as a crack dealer form the connective tissue of Ready to Die. Songs like “Everyday Struggle” and “Suicidal Thoughts” surgically detail the stress, paranoia, and depression from his pre-Bad Boy career. As an album that articulated the psychological trauma that lingered from Biggie’s time as a dealer, much of Ready to Die was evocative of the most commercially successful form of hip hop at the time of its release: gangsta rap.  

A primarily Los Angeles-based phenomenon, gangsta rap in the mid eighties fixated on drug sales and violence in a way that East Coast rap had not. There had been those occasional references to street hustles in rap music, but records that focused explicitly on first-hand criminality, like Philadephia MC Schoolly D’s “P.S.K. (What Does It Mean?),” remained mostly on the fringes. In South Central Los Angeles, which suffered through the crack epidemic as subsets of two powerful street gangs—the Bloods and Crips—fought for territory, violence in rap music took on a new significance.

Future Law & Order: SVU star Tracy “Ice-T” Morrow, a New Jersey native transplanted to Los Angeles in the 70s, was a progenitor of gangsta rap who had adopted a pimp persona inspired by L.A. writer and actual pimp Iceberg Slim. The introduction to his 1987 album Rhyme Pays conveys Ice T’s fictional backstory: after becoming a young gang banger, he gains notoriety for his rap skills. Unlike the stories of Biggie, Nas, and Raekwon, Ice-T’s lyrical prowess doesn’t offer an escape, but a means of operating within his already established lifestyle. “He was crowned the West Coast MC king,” the narrator explains, “But after his inauguration, there was a rush of wack rappers with one intention: to crush this master rapper and take his throne.” Battle rapping and vying for the title of the best MC had long been a part of hip hop culture, but in Los Angeles hip hop, the ideas of battle rapping and gang warfare often comingled. This contention between rappers mirrored the jockeying for position of the Bloods and Crips, causing Los Angeles rap to be darker and bloodier than its New York counterpart, and shaded with a deep paranoia. When N.W.A.—the group that came to define gangsta rap with its 1988 album Straight Outta Compton—had a falling out, the members made gruesome threats toward one another in their music.  Andre Romelle Young (Dr. Dre) directed the song “Fuck with Dre Day” toward his ex-bandmate Eric “Eazy-E” Wright. “Used to be my homie, used to be my ace. Now I want to slap the taste out your mouth,” Dre hisses on the track. A short time later, Eazy-E topped Dre’s threats on the mini album It's On (Dr. Dre) 187um Killa, spitting, “Give up your shit or take two to the chest with the Cripness.”

O’Shea “Ice Cube” Jackson, Jr., another former member of N.W.A., mostly stayed out of the interpersonal beef, opting instead to take his brand of gangsta rap in different direction. Jackson’s solo albums AmeriKKKa’s Most Wanted (1990) and Death Certificate (1991) cast Ice Cube as an obstinate villain—a misogynist, intemperate gangsta who thrived on people’s hate—which allowed him to couch incendiary political ideas within his songs. But Ice Cube’s biggest crossover hit may be his most subversive. As he begins to describe an idyllic 24 hours on “It Was a Good Day,” he takes a moment to wonder if he’ll even be alive by the time tomorrow comes around—a sort of nihilist version of seizing the moment.  The subsequent action is defined as much by what doesn’t happen as what does happen. On this day in Los Angeles, there’s no smog; no one tries to shoot Ice Cube or jack his car; the police don’t harass him; none of his friends get killed; at no point does he even have to use his assault rifle. “It Was a Good Day” is as much a fairy tale as “Juicy”; Ice Cube even tips his hand at the end as he calls for his DJ to stop the track and wonders, “What the fuck am I thinking about?” The perfect world in “It Was a Good Day” doesn’t have any of the luxuries that Biggie describes in “Juicy.” Ice Cube’s successes include relatively mundane achievements like winning money at craps, shooting some hoop, and finally getting a date with a woman he’s long desired. Mostly, he just avoids the stresses of his day-to-day life, the things that would threaten his well-being.

“It Was a Good Day” appeared on Ice Cube’s third album, The Predator, released on November 17, 1992, precisely two weeks after Bill Clinton was elected president. In the run up to the election, a number of political flashpoints sprung up around gangsta rap: the acquittal of the police officers who had been videotaped brutally assaulting Rodney King and the ensuing riots in South Central Los Angeles publically highlighted the racial unease that gangsta rappers had been talking about for years; Ice-T and other rappers took heat from politicians for their incendiary lyrics, culminating in Clinton publicly criticizing an activist named Lisa Williamson (better known as “Sister Souljah”) in a calculated move to win centrist voters; and underneath it all raged a debate as to whether or not gangsta rap lionized and inspired real-life violence.[7] Against this backdrop, it is striking just how prosaic the events of “It Was a Good Day” are. The song is not intended to be taken as realism—after all, toward the end, Ice Cube looks into the night sky and sees his name flashing on the Goodyear Blimp—but Cube raps about AK-47s and carjackings with the same measured nonchalance as he describes what he has for breakfast.

Of course, it would be inaccurate to say that no gangsta rappers sensationalized the violence on the streets of Los Angeles. Many Los Angeles artists capitalized upon the middle class’s fear of the ghetto and portrayed neighborhoods in South Central or Compton as terrifying places where death at the hands of another man was both routine and inescapable. As the subgenre gained commercial success, plenty of its artists worked to instill the same paranoia in the music industry that they portrayed in their raps. Marion “Suge” Knight, Dre’s boss at Death Row Records, became known for his affiliation with the Bloods and his use of violence as a negotiation tactic. Famously, he allegedly convinced Vanilla Ice to sign over royalties from his inescapable hit “Ice Ice Baby” by dangling him off of a hotel balcony by his ankles. Knight began an acrimonious rivalry with Sean Combs, taking (figurative) shots at Puffy’s thirst for the spotlight, dissing him for showing up on Bad Boy artists’ songs and dancing in their videos. The Death Row-Bad Boy rivalry quickly got branded as a West Coast-East Coast beef, and ultimately came to define mid-nineties rap. Caught in the coastal crossfire, The Notorious B.I.G.—who had imagined “living life without fear” as a byproduct of his success—ultimately became plagued in the music industry by the same paranoia that accompanied his days as a drug dealer.

In 1995, Knight signed Tupac Shakur to Death Row. The son of Afeni Shakur and Billy Garland, two active members of the Black Panther Party, Tupac grew up studying theater, dance, and poetry in Harlem and Baltimore before moving to Marin County, California, at seventeen. He began his rap career with the Bay Area alternative rap collective Digital Underground—whose classic 1990 album Sex Packets is almost Dadaist in its absurdity—but became fixated on gangsta rap as his solo career unfolded. In Michael Eric Dyson’s biography of Tupac, director John Singleton (who worked with Shakur on the movie Poetic Justice) speculates that Tupac began to model his own life after that of a gang-banger. “For the sake of the whole rap game…he crafted the image [of the gangsta] for himself. He started to live that image out and that’s what led to a lot of his troubles.”[8] Between 1993 and 1995, Tupac was arrested multiple times. He beat up a rapper named Chauncy Winn with a baseball bat;[9] was found guilty of assaulting Menace II Society director Allen Hughes;[10] and, though the charges were ultimately dropped, he shot two off-duty police officers in Atlanta.[11] In 1995 he signed to Death Row because Suge Knight put up $1.4 million in bail to get him out of prison, where he had served nine months on a sexual assault charge.[12]

On November 18, 1993, Tupac brought a nineteen-year-old woman to his room at the Parker Meridian Hotel, where three of his friends allegedly raped her. Though his involvement in the rape itself has been debated, Tupac was ultimately sentenced to one-and-a-half to four-and-a-half years in prison for sexual abuse. In 1991, a similarly gruesome attack occurred when N.W.A.’s Dr. Dre allegedly pushed television personality Dee Barnes’ head into a brick wall and threw her down a flight of stairs.[13] The incidents highlight one of the darkest sides of gangsta rap—a hateful and sometimes violent relationship with women that was depicted in its music, and then frequently manifested in real life. The pimp persona adopted by Ice-T and other rappers leant a metaphor to something that was already implicit in many gangsta rap lyrics: women were often considered possessions, grouped in with rappers’ other status symbols, and were treated as such. Gangsta rap’s attitude toward women, coupled with its commercial success, seemed to give many rappers permission—even incentive—to perform sexist lyrics, and gave credence to the generalization that hip-hop culture itself was misogynist.

On November 30, 1994, while on trial for rape, Tupac was shot five times in the lobby of Quad Recording Studios in Manhattan where his then friends Puff Daddy and the Notorious B.I.G. were upstairs, recording. While in prison, Tupac assigned blame for his shooting to Biggie and Puffy,[14] and Suge Knight was easily able to enlist him in Death Row’s war on Bad Boy Records. Tupac spewed venomous raps toward Biggie, Puffy, and other New York artists, repeatedly threatening to kill them. Eventually, the street violence of the recordings became real. In September 1996, Tupac died from gunshot wounds sustained in a drive-by shooting in Las Vegas. A little less than two weeks later, Death Row released the single “To Live and Die in L.A.,” which had been recorded by Tupac under the pseudonym Makaveli.

“To Live and Die in L.A.” is a thematic sequel to Tupac’s biggest hit, “California Love,” but it’s also an interesting parallel to “It Was a Good Day.” Ice Cube portrays his Los Angeles neighborhood through a mundane day where everything happens to go right. There’s an ever-present threat of violence that is never realized; a subconscious uneasiness even on the best of days. Tupac, out on bail and seeing his adopted home with a fresh perspective, glorifies the gang warfare in Los Angeles. As the son of two black activists, he viewed the Bloods and Crips through the lens of community, seeing them as an evolution of the Black Panthers that had simply gotten out of control. While singer Val Young coos that L.A. is “the place to be” on the hook, Tupac renounces street violence while inadvertently condoning it, even trivializing it by calling it “drama like a soap opera.” At one point, a close friend of Tupac’s is killed for showing off his money to a crack fiend, and he calls the friend’s death “a hard lesson,” rationalizing the murder because his friend had been flaunting his wealth. Whereas Ice Cube’s L.A. sees adversities such as poverty and violence as grimly commonplace, Tupac fetishizes them. Shakur, the former drama geek who as a teenager performed in A Raisin in the Sun at the Apollo Theater in Harlem, creates an operatic version of South Central LA—much the way The Notorious B.I.G. uses symbols of affluence to create a mythological version of wealth.

“To Live and Die in L.A.,” 1996              

The parable of Tupac’s friend and the crack fiend in “To Live and Die in L.A.” illuminates one of the aspects of Biggie’s “life without fear” that wealth promised. The upper class appeared to offer insulation from the poor. The mansion used in the “Juicy” video seems geographically isolated in a way that Biggie’s stoop in BedStuy could never be. The projects, as described by Nas and Treach, literally stacked the poor on top of each other in high-rises. Even extreme success as a drug dealer meant constantly interacting with the impoverished, because they made up the core of your clientele. What’s more, the crack epidemic had a very specific significance in black neighborhoods, because crack addiction so was so thoroughly crippling that dealers’ success came at the cost of disabling others in their own community. Gangsta rap thrived on that cycle of poverty, enlightening it for a largely suburban audience while refusing to live outside of it. For Biggie Smalls, rap promised an escape from poverty as well as a reprieve from having to live among the poor.

In an interview with B.E.T. leading up to the release of his second album, Life After Death, Biggie told Rap City’s Joe Clair, “I can’t rap about being broke no more. I ain’t broke! I can’t rhyme about hustling in the streets no more because I don’t hustle no more. So it’s the life after. All that’s over with now. I ain’t hungry no more.”[15] Ready to Die found Biggie trying to cope with the trauma from his criminal past as he embarked on his rap career. Though he rapped about his financial success in the first person, his bank account hadn’t yet benefited from his hard work. Perhaps the fiscal ambition on Ready to Die was a Puffy-inspired form of positive actualization. On Life After Death, Biggie attempts to reconcile his legitimately acquired wealth with his still-present felonious tendencies. “Somebody’s Gotta Die,” the opening song on Life After Death begins with Biggie at home “dreamin’ about Learjets and coupes,” when he’s interrupted with news that his friend C-Rock has been violently ambushed and is in critical condition. In spite of his new social status, he immediately vows revenge. “Retaliation for this one won't be minimal,” he spits, “‘cause I'm a criminal way before the rap shit/ Bust the gat shit, Puff won't even know what happened.” Later, on tracks like “What’s Beef?” and “My Downfall,” Biggie is concerned with unnamed rivals that threaten to kill him—and he goes to lengths to make sure he gets to them first. He never calls out Tupac by name, but the implication is clear.

On the other side of the spectrum, money is still a major issue. Songs like “Sky’s the Limit” and “I Love the Dough” follow the aspirational blueprint of “Juicy,” but without being grounded in the same details of Christopher Wallace’s BedStuy childhood. They just keep increasing Biggie and Puffy’s credit limit without regard to the APR. Where the “Juicy” video featured Biggie throwing a pool party at his mansion, the video for “Hypnotize,” the first single from Life After Death, opens with Biggie and Puffy on a yacht, getting chased by three helicopters. As Biggie races the yacht across the ocean, hundred-dollar bills get blown off the sides into the water. Puffy holds onto the windshield, dancing while trying not to fall down. Later, the duo reemerges in a parking garage. After a moment, a dozen black motorcycles and a hummer flood in and attempt to apprehend them. These assailants could be the federal agents Biggie mentions elsewhere on Life After Death, but it’s notable that he never names what he’s running from or why. The helicopters and motorcycles are just a shadowy, omnipresent force that won’t leave him alone. That sense of foreboding—whether a direct or indirect result of the threats from Tupac and Suge Knight—pervades Life After Death, and would turn out to be sadly prescient. Money hadn’t bought The Notorious B.I.G. a life without fear. It had only introduced more problems.

“Hypnotize,” 1997              

On March 8, 1997, The Notorious B.I.G. co-presented the award for Best R&B/Soul Single at the Soul Train Music Awards, held in Los Angeles. He stood behind Puff Daddy, Brian McKnight, and the Bad Boy R&B group 112 while they read the nominees. As he made his way through the posse to the microphone to announce the winner, boos rippled through the audience at LA’s Peterson Automotive Museum. He responded with a bemused “Whassup Cali!” A couple of hours later, as he drove away from the venue, a Chevrolet Impala pulled up next to him on Wilshire Boulevard. A man in a bowtie fired a 9mm pistol into his GMC Suburban SUV, a drive-by shooting that had eerie echoes of the Las Vegas murder of Tupac. Four bullets hit Biggie Smalls, and by 1:15 AM on March 9, he was dead. Sixteen days later, Bad Boy Records released his new double album, the macabrely titled Life After Death.

Publicly mourning his friend, the CEO of Bad Boy records was also tasked with promoting The Notorious B.I.G.’s posthumous release, building the career of recent label signee Mason “Ma$e” Betha, and prepping his own debut—Hell Up in Harlem—for release. Puff Daddy’s first single as a lead artist hit number one on Billboard before Life After Death came out, and stayed there for six weeks until being displaced by “Hypnotize.” That track, “Can’t Nobody Hold Me Down,” codified Puffy’s songwriting formula. It picked a recognizable sample (in this case the beat from Grandmaster Flash & the Furious 5’s “The Message”) and interpolated a popular hook for the chorus (Matthew Wilder’s “Break My Stride”). “Hypnotize” followed the same pattern, sampling Herb Alpert’s “Rise” and flipping a line from Slick Rick’s “La Di Da Di.”

The price of sampling had increased dramatically since the early nineties, after popular artists like MC Hammer and Vanilla Ice were sued by stars like David Bowie, Queen, and Rick James for copyright infringement. Puff Daddy, however, repeatedly proved willing to pay for the rights to well-known songs and the investments frequently paid off. From March 22 to September 27, 1997, singles produced by Puff Daddy held the Billboard number one spot for all but three weeks. Eleven of those weeks belonged to “I’ll Be Missing You,” a tribute to The Notorious B.I.G. built around The Police’s “Every Breath You Take.” In a move that seemed out of character for the consummate businessman, Puffy gave The Police’s lead singer Sting one hundred percent of the publishing rights to “I’ll Be Missing You.” Though his tribute to Biggie quickly became one of the best-selling singles of all time, Puffy wouldn’t make any money from it directly. Nevertheless, the success of the song helped his album—glibly retitled No Way Out after his friend’s death—sell 561,000 copies its first week out.

The video for “Hypnotize” was in the can before Biggie’s death. For the follow-up single, Puffy and guest-rapper Ma$e—Bad Boy’s new flagship artist in the wake of The Notorious B.I.G.’s murder—had to carry the video’s narrative weight. In the Hype Williams-directed piece, the duo, styled in primary-colored outfits made of a glossy, windbreaker-like material, dance in front of the Queens Unisphere in blue and on a conveyer belt through streaks of fluorescent light in red. In yellow, they hover weightlessly in the center of a control room, operating dials that allow them to beam in Biggie Smalls. Before The Notorious B.I.G.’s rap begins, the music cuts out and a clip from an old interview plays. Reclined so far back in his chair that the camera is almost looking up at him, Biggie laughs as he explains the song’s premise: “The more money you make, the more problems you get, and jealousy and envy is just something that comes with the territory.”

“Mo Money Mo Problems” is one of The Notorious B.I.G.’s boldest attempts to cross over to pop radio, riding on a catchy Diana Summer sample from her 1980 hit “I’m Coming Out.” It is a strange song in The Notorious B.I.G.’s catalogue, as the first two verses belong to Ma$e and Puff Daddy, both of whom had their own albums coming out that year. His extended verse anchors the song, but with Biggie gone and Puffy and Ma$e starring in the video by necessity, “Mo Money Mo Problems” felt more like a promotion for the Bad Boy roster than for Biggie himself. If “I’ll Be Missing You” gave Puffy the national spotlight, “Mo Money Mo Problems” completed his pop takeover. He had always been an intuitive self-promoter, but now he became the face of his own brand.

Hype Williams’ imagery from “Mo Money Mo Problems” video came to define an era in rap and R&B. Williams’ aesthetic stood in sharp contrast to the prevailing grimy imagery of gangsta rap. Artists like Tupac thrived on their perceived authenticity, but Williams’ use of effects like the fisheye lens, conveyer belts and the air chamber in “Mo Money Mo Problems” gave his videos a polished, slick, futurist style that bucked the hyperrealism of the gangsta era. His visual language synergized perfectly with Puffy’s opulence. Williams often spent vast sums of money on videos—he once spent nearly $1 million building a fake, Citizen Kane-style mansion in a New York shipyard[16]—but was also unafraid to toy with artists’ public images. He fit Trevor “Busta Rhymes” Smith into a straightjacket in one video, and dressed Missy “Misdemeanor” Elliot in a giant trash bag in another.

Stylist June Ambrose gave many of Williams’ videos a fashion-forward sensibility that accentuated artists like Puffy’s bids for mainstream stardom. When Williams requested a red leather suit for “Mo Money Mo Problems,” Ambrose, inspired by the shiny fabrics from Carnival in the Caribbean, presented him with a red metallic one. Seeing the glossy suit in person, Puffy was nonplussed. Ambrose, who had interned at Uptown Records while Puffy was still there, had to plead with him to even put it on; but once he saw it on video, Puffy was convinced.[17] Apparently so was the rest of the rap industry, as similar looks started to show up all over the place. The shiny suit look seemed mandatory for all Bad Boy artists; and R&B artists from Sisqo to Brian McKnight sported them as well. Nascent movie star Will Smith donned a pink shirt and sparkly grey jacket in the video for “Gettin’ Jiggy with It,” a disco-tinged paean to flashiness that even subtly undermines the gangsta mentality by bragging about expensive seats to watch N.W.A.’s beloved football team, the Raiders. With Smith’s cosign, the shiny suit era of rap reached peak visibility.

“Mo Money Mo Problems,” 1997              

One of the more notable transformations of the shiny suit era occurred with a rapper who had positioned himself as a running mate to The Notorious B.I.G. Biggie had appeared in a video for a promotional single for Shawn Carter’s debut album, sitting at a table of rap luminaries playing Parker Brother’s Monopoly with real money. The song was “Dead Presidents,” copping both its name and a sample of the Nas line from “The World is Yours.” The video begins with Carter—who took the handle Jay-Z from the J-Z subway station in his Brooklyn neighborhood[18]—climbing out of a helicopter and into a Mercedes Benz, which he then takes around his neighborhood to collect earnings from drug money. Jay-Z has a dispassionate, pragmatic approach to wealth—it’s just the result of doing business. At one point, he mimics the voice of another dealer saying, “I want money like Cosby,” before responding, “Who wouldn’t? It’s this kind of talk that make me think you ain’t got no puddin’.”

Jay-Z’s debut album, Reasonable Doubt, which followed “Dead Presidents” in 1996, is a peak of the subgenre Mafioso rap, an East Coast analog to gangsta rap with rappers portraying themselves as members of a crime syndicate, rather than dealing with street-level gang warfare. Jay-Z positions himself as a don. He possesses wealth akin to Biggie’s, but it isn’t from the music industry. Then, in the wake of Puff Daddy’s success, Jay-Z’s music took a sharp turn. Primarily produced by Puffy’s stable of Bad Boy producers, the Hitmen, Jay’s second album, In My Lifetime, Vol. 1., veers wildly toward the pop charts. He holds on to the drug dealer persona, but puts a shiny suit on it. “The City is Mine” utilizes the hook and saxophone riff from Glen Frye’s “You Belong to the City.” The next track takes inspiration from The Waitresses 1982 new wave hit “I Know What Boys Like.” Reasonable Doubt was an artistic success, but it was In My Lifetime that started to get Jay-Z in heavy rotation on MTV.

West Coast hip hop flamed out after Tupac’s death. Death Row’s only remaining star—Calvin Broadus, Jr., better known as Dr. Dre’s protégé Snoop Doggy Dogg—left the label, accusing label head Suge Knight of involvement with Tupac’s murder.[19] Knight, who was also widely suspected of The Notorious B.I.G.’s murder, had been sent to prison on parole violations, and was ultimately sentenced to nine years. The bottoming out of gangsta rap created a vacuum in the hip hop marketplace that Puff Daddy was happy to fill. Inescapable on radio and television, Puffy was in demand as both a producer and a guest artist. Established stars began to rework their styles toward the Bad Boy sound. Puffy helped Mariah Carey shift toward a more hip-hop-friendly audience, produced a single for LL Cool J, and teamed up with Nas for “Hate Me Now,” accompanied by a video that featured the two getting crucified. In 1998, he made the most extravagant of all sample purchases, hijacking Led Zeppelin’s “Kashmir” for a song on the Godzilla soundtrack—even convincing Jimmy Page to play guitar on the track and appear in the video.

All of these things—expensive samples, shiny suits, fisheye lenses, fluorescent lights, flaunted wealth—came to define the aesthetic of Puffy's pop reign. At one point in the “Mo Money Mo Problems” video, Puffy and Ma$e brandish Rolexes on their wrists, hold them up and wave them in front of the camera. It’s the kind of thing that Tupac describes his friend getting killed for in “To Live and Die in LA,” shrugging off the murder as “a hard lesson.” But, aside from the expensive samples, those visual choices came through directors and stylists. Puffy’s own iconography of wealth ran on a slightly different track. On “Mo Money Mo Problems,” Puff wanted to pay tribute to twenty-one-year-old Tiger Woods’ recent victory in the Masters tournament, so the video opens with him on the golf course, sinking a winning putt of his own. The golf course scenes feel shoehorned into the video—the blue sky, lush green grass, and predominantly white audience don’t match the rest of Hype Williams’ shots at all.

Sean Combs’ golf game and country club attire are additional white upper-class status symbols, following the mansions, yachts, Rolexes, and even the pool he begged his mother to buy him as a child. The social status purchased with money seemed to be of primary importance to him. As his income increased thanks to the monster success of Bad Boy in the late nineties, so did his investment portfolio. He launched a line of sportswear called Sean Jean in 1999, and rented out a window at Bloomingdales to promote it. He hired a personal valet, Farnsworth Bently, who appeared in his videos. He threw white-tie parties in the Hamptons and appeared alongside Jerry Seinfeld on the cover of Forbes. In his art and in his life, Puffy was appropriating the symbols of old money, a primarily East Coast phenomenon in America, and one that he would have frequently interacted with while growing up in Westchester County. In doing so, he cast himself in the role of the nouveau riche, which he played to the stereotypical hilt.

In the video for 2001’s “Bad Boy for Life,” Puffy, now using the name P. Diddy, moves into a placid suburb called Perfectown, U.S.A. The neighbors suspiciously ogle Diddy’s tour bus as it pulls up to his new house, and one woman faints as his entourage spills out onto the lawn. The tension gets quickly dissipated, though, as his fellow suburbanites eagerly join him, snorkeling in the above-ground pool and cruising the cul-de-sac in souped-up low riders. Even when he sails a black golf ball from his rooftop through his neighbor Ben Stiller’s window, Stiller returns it and asks to be invited to the next house party. At one point, Ice Cube, Snoop Dogg, and West Coast acolyte Xzibit join the festivities, as Los Angeles Lakers center Shaquille O’Neal faces off in a driveway basketball game with Puffy, who is wearing an officially licensed Shaquille O’Neal replica jersey. Nearly five years after the death of Biggie Smalls, East Coast and West Coast factions of hip hop unite in the upper-middle-class white suburb that Sean Combs has taken over.

“Bad Boy for Life,” 2001              

Before the turn of the millennium, Puff Daddy’s influence on hip hop music had waned, but there had been a paradigm shift in the mentality of recording artists. Rapping was no longer just a way to get a record deal; it was an entrance point to the world of business. Puffy’s success proved that a hip hop mogul could be the face of his own brand. Artist-driven independent labels like Percee “Master P” Miller’s No Limit in New Orleans and Ronald & Bryan “Birdman” Williams’ Cash Money flourished. It became common practice for major labels to offer stars their own label imprint, as Interscope did with Dr. Dre’s Aftermath Entertainment, Marshall Mathers’ Shady Records, and Curtis “50 Cent” Jackson III’s G-Unit Records. Rappers like 50 Cent, whose album Get Rich or Die Tryin’ sold 5 million copies in the summer of 2003, would pursue multiple sources of income such as clothing lines, film and television, and sneakers. One of Jackson’s investments was in a burgeoning soft drink company called Glacéau, based in his home-borough of Queens, New York. The company’s leading product reminded Jackson of the flavored water you could buy for twenty-five cents in any bodega where he grew up, which inspired a flavor named after him: Vitaminwater Formula 50. In 2007, the single “I Get Money” began with 50 describing the return on his investment: “I took quarter water and sold it in bottles for two bucks. Coca-Cola came and bought it for billions, what the fuck?”

In the early 2000s, Jay-Z took over the mantle of best rapper alive. His intricate lyricism proved him a worthy successor to The Notorious B.I.G., and the fact that he had gotten Biggie’s cosign before his death made Jay-Z something of an heir to his throne. He’d cofounded Roc-a-Fella Records (with Damon Dash and Kareem Burke) as an independent label before finding distribution—first on Priority, then on Def Jam Recordings, owned by the Universal Music Group. In 1998, an audacious sample of “It’s the Hard Knock Life” from the musical Annie spurred a breakthrough single in “Hard Knock Life (Ghetto Anthem),” and helped his third album go platinum five times over. From there, he put out an album a year—each selling no less than two million—until 2003, when a 33-year-old Jay-Z shocked his fans by announcing his retirement. His send-off would include one last album, a star-studded farewell concert at Madison Square Garden, and a documentary called Fade to Black.

Throughout his run of extremely successful albums from 1996 to 2003, Jay-Z was able to hold onto the Mafioso mystique he’d established on Reasonable Doubt. Whenever he referenced his wealth in his lyrics, he was ambiguous as to whether he’d acquired it through the drug trade or his Roc-a-Fella business interests and Rocawear clothing line. His ambitious “final” record, The Black Album, attempts to secure the legacy of both Jay-Z the rapper and Jay-Z the Scarface archetype he often portrayed. “Allure” weaves an elaborate metaphor that pits his personal ambition against his love of the hustle. He lists the things money has bought him—Japanese sneakers, Swiss watches, Italian vacations—before admitting that he often feels like he’s just going through the motions of his day job. The lifestyle is hard to resist (“The game is a lightbulb with eleventy-million volts and I'm just a moth addicted to the floss”) but he fears it will kill him. The end is ambiguous. “I mean even James Dean couldn’t escape the allure,” Jay raps, “dying young, leaving a good-looking corpse, of course.”

The Black Album was Jay Z the rapper’s good-looking corpse. He used it to put a bow on everything he had achieved—retelling the story of his childhood, reveling in his successes, and firing some parting shots at rival MCs who had crossed him. Retiring at the peak of his popularity, Jay-Z addressed his choice to chase commercial success after Reasonable Doubt on “Moment of Clarity”: “I dumbed down for my audience to double my dollars,” he confesses, “We as rappers must decide what’s important, and I can’t help the poor if I’m one of them. So I got rich and gave back. To me that’s the win-win.” But, like Puffy, one of Jay-Z’s greatest skills was thinking five steps ahead business-wise, so The Black Album also helped the public transition into the new phase of his life. “Allow me to re-introduce myself,” Jay declares on the aptly-titled “Public Service Announcement.” “I used to move snowflakes by the O-Z. I guess even back then you can call me CEO of the R-O-C,” he spits, a double-entendre on the name of the label he founded and the crack rocks he used to sell as a street dealer. “Fresh out the fryin’ pan into the fire, I be the music biz number one supplier.” While it lists Jay-Z’s drug dealer bona-fides, the song’s corporate vernacular also forecasts the next era of his career. On December 8, 2004, a little more than a year after the release of The Black Album, Jay-Z was named president and CEO of Def Jam Recordings, one of the most storied and iconic labels in hip hop.

Of course, Jay-Z didn’t completely give up rapping after The Black Album. He’d still show up in guest spots on his Roc-a-Fella and Def Jam associates’ records. On his protégé Kanye West’s “Diamonds from Sierra Leone (Remix),” the newly-minted CEO picked up right where he left off: “I sold kilos of coke, I’m guessing I can sell CDs,” Jay-Z says of his new corporate lifestyle, “I’m not a businessman; I’m a business, man!” Ironically, after all his years comfortably chasing wealth “by any means necessary” (as Jay Z would often re-appropriate Malcolm X’s civil rights phrase to describe his financial pursuits), he’d shown up on a track that didn’t have quite as clean a conscience when it came to drug money. Concerned with the blood diamond trade in Africa, West raps, “Though it’s thousands of miles away, Sierra Leone connects to what we go through today. Over here it’s a drug trade, we die from drugs. Over there they die from what we buy from drugs.” Diamond jewelry had long been a status symbol in hip hop culture; here was a rapper suggesting that rap’s allegiance to wealth might have socio-political reverberations.

West had been a producer in Jay-Z’s stable in the years before his retirement, and (along with Justin “Just Blaze” Smith) had helped him redefine his musical aesthetic with 2001’s The Blueprint, which replaced the slick opulence of the Puffy-era late nineties with a more soulful sound that seemed to inspire an emotional transparency in Jay-Z. As a producer, Kanye had a talent for judging the marketplace. He was, in sports terms, a student of the game. Before hooking up with Roc-a-Fella Records, Kanye had been ghost-producing for Bad Boy. He’d seen the crossover success that Puff Daddy had sampling middlebrow rock icons like Led Zepplin, David Bowie, and Sting. With Jay-Z, he replaced those hooks with less-obvious samples of artists like David Ruffin, Bobby Bland, and Eddie Kendricks. West’s production style was reminiscent of Puffy’s work at Uptown and with The Notorious B.I.G. He chose source material that conjured similar black-middle-class nostalgia, songs that would be immediately familiar to those who’d been around for the birth of hip hop in the mid 70s.  As a rapper, he was one hell of a producer. West spent years begging for an opportunity to drop his own rap album before Roc-a-Fella finally signed him as an artist—mostly to prevent the loss of his production talents to a rival.

The P. Diddy era had, perhaps inevitably, devolved into hip hop as product placement; for example, in the video for Busta Rhymes’ “Pass the Courvoisier II,” he and Puffy are mere accessories to the cognac’s iconic bottle. While the success of 50 Cent’s Dr. Dre-produced album sparked a gangsta rap resurgence at the top of the charts, Jay-Z’s retirement had left hip hop with a power void; there was no one rapper who possessed his charismatic mix of skill and credibility. In the midst of this, Kanye West positioned himself as an alternative voice. The persona he chose for his debut album, The College Dropout, was a middle-class black everyman whose primary concerns weren’t the life and death stakes of street crime and gang warfare, but tuition and his job at The Gap. This allowed him to address racial politics from the point of view of a curious student, playing all sides of a question. He coveted jewelry, but worried about where it came from and how he could afford it; he wore Versace but pronounced it “ver-say-see.” On “All Falls Down,” over an interpolation of a Lauryn Hill song called “The History of Inequity,” he debunks the gangsta myth: “Drug-dealer buy Jordans/ Crackhead buy crack/ And a white man get paid off of all of that.” Kanye wanted the same wealth that Biggie and Puffy had described in “Juicy,” but recognized that money itself came at an unseen cost.

In 2006, a mere three years after his retirement, Jay-Z resumed his rap career. Untethered from his drug dealer persona, his comeback album cast him as the “business, man” he’d described on “Diamonds from Sierra Leone.” On Kingdom Come’s “30 Something,” he describes his evolution from street hustler to CEO by comparing his purchases. “I don’t got the bright watch,” he boasts, “I got the right watch. I don’t buy out the bar, I bought the nightspot. I got the right stock, I got stockbrokers that’s movin’ it like white tops.” Celebrating his white collar turn, he wryly brags about not having to flaunt his wealth. He doesn’t need the diamond-encrusted gold watch anymore; he’ll take the streamlined Swiss construction of a Franck Muller. The thing about luxury brands is that you don’t know what they are until you can afford them. The way that you’re asking makes Jay-Z think you don’t have any pudding.

Of course, Jay-Z’s audience rejected Kingdom Come wholesale, finding his boardroom baller persona alienating. His follow-up didn’t fare much better. A companion album to the Ridley Scott movie of the same name, American Gangster allowed him to slip back into his drug dealer guise, roleplaying a man whose claim to fame was figuring out how to brand and market crack. In on the act now, the fans didn’t buy it. American Gangster ended up as his lowest selling solo album ever. With his music, Jay-Z appeared to have an image problem, but his priorities had also changed. He had become a master of increasing his revenue streams. In 2007, he stepped down from Def Jam, having had considerable success signing talent during his tenure. A couple of years later, he bought out his own contract to sign a better deal with Live Nation and Sony Music. The sports bar he referenced in “30 Something,” the 40/40 Club, expanded from New York to locations in Atlantic City and Las Vegas. He became a part-owner of the New Jersey Nets and helped them move to Brooklyn—so close to his own neighborhood that when he wanted to light a candle for each of his eight shows at their new stadium, Barclay’s Center (in which he also owned a small stake), he borrowed a menorah from the man who lived in his old stash spot.[20] A year later he sold his shares in Barclay’s in order to become a sports agent, just in time to net former New York Yankee Robinson Canó a $240 million deal with the Seattle Mariners. Retiring ahead of taking over as president of Def Jam had seemed like a calculated move, but it was only the beginning of a long series of public moves that reflected Jay’s surgical business acumen. He had learned the first lesson of Wu-Tang Financial: diversify.[21]

By 2011, Kanye West’s on-record interests had shifted as well. He was less self-conscious about money than about his public image and the trappings of fame. A collaborative album with Jay-Z would be a slight course correction. Designed by Ricardo Tisci of Givenchy, a luxury brand of haute couture clothing and accessories, the cover of Watch the Throne takes a page out of the Donald Trump handbook of luxury design and features geometric flowers chiseled out of pure gold. The album follows suit, as Jay-Z and West celebrate an excess of wealth that even Biggie and Puffy could never have imagined. On “Otis,” Kanye compares his lyrics to the prestige brands he indulges in: “Couture level flow is never going on sale/ Luxury rap, the Hermes of verses/ Sophisticated ignorance, write my curses in cursive.” He lounges in his pajamas on a private jet while Jay-Z is at home, laying face-down on a million dollar bills. Jay had often compared the music business to the act of selling crack; on Watch the Throne, he seems to be adapting George Carlin’s famous line about cocaine to his financial interests. How does money make you feel? It makes you feel like having more money.

Watch the Throne galled a significant portion of its listeners. Its release came in the middle of the Global Financial Crisis, and Kanye and Jay-Z appeared to still be gleefully floating in the pre-recession economic bubble. The video for “Otis” features the duo taking a blowtorch and circular saw to a Maybach before customizing it, piling four female models into the backseat, and taking it for a spin in front of a giant American flag, also designed by Ricardo Tisci. The album’s whole campaign felt like it had a similar attitude. The duo’s excess wealth had turned into disposable income, and they were lighting it on fire. They had transformed from being merely wealthy to identifying with a faction now vilified by media coverage thanks to the Occupy Wall Street Movement: the one percent of America’s population that reportedly controls forty percent of the nation’s money.[22] It was the most extreme version of Tupac’s friend in “To Live and Die in LA” bragging about money to a derelict, “trying to floss on him, blind to a broken man’s dream.” Like Sean Combs adopting the symbols of the nouveau riche, Watch the Throne is an act of seditiousness, celebrating what Jay describes on “Murder to Excellence” as “black excellence, opulence, decadence” in a country that has historically been openly hostile to it. On “Made In America,” when Jay-Z raps, “Only spot a few blacks the higher I go/ What’s up to Will/ Shout-out to O/ That ain’t enough, we gonna need a million more,” he hints that black wealth in America is still a revolutionary idea.


Jay-Z’s call for a million more black Americans to join him amongst the upper class has echoes of Puff Daddy’s “Bad Boy for Life” video. Puffy depicts members of the white upper-class unexpectedly embracing him on their own turf. Money buys him the house, yet his swagger charms the neighbors. Puffy’s post-racial utopia of Perfectown, U.S.A.,may be ironic, but his and Jay-Z’s shared belief that wealth can buy a voice among the elite seems sincere. It’s a thoroughly capitalist approach to addressing racial inequality. Yet the inverse also appears to be happening to the rappers—as they adopt the lifestyle of the upper class, they become insulated. Their connection to the poor now seems tenuous. In a self-penned article for XXL Magazine, Kanye describes himself as “the sweet spot between the hood and Hollywood. Having a conversation with Karl Lagerfeld and Jay-Z within the same hour.”[23] In his failed attempt to create a dichotomy between the fashion designer and the rapper, he forgets (or ignores) the fact that he’s simply having conversations with two different very rich people. In his insular world, the hood is no longer actually represented.

Jay-Z in particular has always seemed to hold himself at an arm’s distance from poverty, ever since driving around his neighborhood to collect drug money in a Benz in the video for “Dead Presidents.” The economic disparity between Jay-Z and his clients is pronounced, but goes unacknowledged in Jay-Z’s rhymes. His Mafioso persona on Reasonable Doubt completely strips gangsta rap of its emotional core and focuses strictly on its industry. The fact that crack dealers and addicts had to survive within the same ecosystem means that making money within that system comes at the expense of your neighbor. When Jay-Z joined the upper class, his emotional distance from the poor seemed to carry over. In an interview with The New York Times, Zadie Smith asked him about the Occupy Wall Street protesters, who at the time of Watch the Throne’s release were camped out in Zuccotti Park. Jay-Z, who refers to himself and his wealthy cohort as “the new black elite” on Watch the Throne, came off as defensive and protective of his status as a one-percenter: “The one percent that’s robbing people, and deceiving people, these fixed mortgages and all these things, and then taking their home away from them, that’s criminal, that’s bad. Not being an entrepreneur. This is free enterprise. This is what America is built on.”[24] When presented with an opportunity to associate himself with a movement for social and economic equality, he balks. When given an opportunity to capitalize, on the other hand, he chases it. Instead of supporting Occupy Wall Street, he co-opted their motto for a series of $22 t-shirts, with all the profit going to Rocawear.[25]

From the genre’s inception, the use of money in hip hop lyrics has consistently paralleled the financial success of the music itself. In its first decade, the notion that one could make a living off of rapping was a revelation. Puff Daddy and Biggie Smalls then set the bar at wealth. Now, Jay-Z and Kanye West count themselves among the world’s elite. “From parolees to hold G’s, sold keys, low keys,” West raps on “Murder to Excellence,” “We like the promised land of the OGs. In the past if you picture events like a black tie, what’s the last thing you expect to see? Black guys. What’s the life expectancy for black guys? The system’s working effectively, that’s why!” His couplets lay out the dilemma: he and Jay-Z are role models to aspiring rappers and entrepreneurs; they and their peers have broken the glass ceiling for black Americans in business; yet, despite their individual successes, violence, drugs, and institutional racism still ravage the very communities that birthed them. Given the complexity of the problem, the proposed solution seems outrageously insufficient: if you don’t want to deal with the hardships of being poor, just make more money.

“Otis,” 2011              

Marty Brown
is an actor and writer living in Brooklyn. A previous essay, “Nothing's Been Authenticated: The Double Hustle of Rick Ross” appeared in our springsummer2011 issue.



[2] Charnas, Dan. The Big Payback. New York: New American Library, 2010.

[3] Poulson-Bryant, Scott. “Puff Daddy.” VIBE Magazine. September 1993.

[4] Coker, Cheo Hodari. Unbelievable: The Life, Death and Afterlife of the Notorious B.I.G. New York: VIBE Books, 2004.

[5] Touré. “Biggie Smalls, Rap’s Man of the Moment.” New York Times. 18 December 1994.

[6] “Brand New RZA Interview." Web blog post transcription of RZA interview with 92Q, Baltimore. Wu Forever. 17 May 2005. 

[7] Giovacchini, Anthony M. “The Negative Influence of Gangster Rap and What Can Be Done About It.” Poverty & Prejudice: Media and Race. 4 June 1999.

[8] Dyson, Michael Eric. Holler If You Hear Me: Searching for Tupac Shakur. New York: Basic Civitas Books, 2001.

[9]“Rapper Tupac Shakur to Face Assault Charge.” Ocula Star-Banner. 9 September 1994

[10] “Tupac Shakur Biography." Rolling

[11] Smothers, R. “Rapper Charged in Shootings of Off-Duty Officers.” New York Times. 2 Nov. 1993.

[12] Charnas, op. cit.

[13] Light, Alan. “N.W.A.: Beating Up the Charts.” Rolling Stone. 8 August 1991.

[14] Charnas, op. cit.

[15] Interview available here.

[16] Pappademas, Alex. “The Career Arc: Hype Williams.” Grantland. 18 July 2012.

[18]  Ramirez, Erika. “20 Stories Behind Rappers’ Stage Names: Waka Flocka, Jay-Z & More.”a Billboard. 3 April 2013.

[19] “Snoop Dogg Beefs Info.”

[20]  Wehle, Amit. “Jay-Z Borrowed My Menorah & Visited My Apt., His ‘Empire State of Mind’ Stash Spot.” 10 October 2012.

[21]  cf. “Wu-Tang Financial.” Chapelle’s Show. Comedy Central.

[22] West, Kanye. “Kanye West’s La Dolce Vida.” XXL Magazine. October 2010.

[23] Smith, Zadie. “The House That Hova Built.” The New York Times. 6 September 2012.

[24] Stern, Remy. “Is Jay-Z Trying to Profit From Occupy Wall Street?” Gawker. 10 November 2011.