While I was sitting in the backseat of my family’s Camry trying to act out the masculine caricatures I’d already absorbed from “Video Music Box,” the hip-hop world was still reeling from the death of The Notorious B.I.G. “All About The Benjamins” was the second single from Puff Daddy’s No Way Out, a debut-turned-eulogy-turned-celebration as schizophrenic and tragic and beautiful as the hustler from Brooklyn who posthumously inspired it.  On its first single, “I’ll Be Missing You,” Puffy mourns his late protégé and best friend with a Sting sample and an old Negro spiritual. It’s a ballad that critic Kelefa Sanneh cites as the beginning of “corporate rap,” or rap music that prioritizes mass appeal and financial gains over artistic merit. But what better symbol is there for corporate rap’s big bang than its larger-than-life founder rising from the dead to squeeze in one more champagne drenched ode to hundred dollar bills? Clever, vain, intricate, glossy, humorous, infectious and just mesmerizing enough to hold the attention of a 6-year-old in the family sedan: “All About The Benjamins” was corporate rap’s blueprint, and Biggie’s verse was its legend.

But Biggie was not a corporate rapper. He was simply incredible at making corporate rap. He bounced between strict artisan and shrewd miser, unable to adhere to the stigmas of either because he was such a balanced composition of both. In one of his last interviews with Jeff “Chairman” Mao, Biggie nags that he’s never been awarded “Dopest Rhyme of the Month” in The Source, and moments later scoffs at the notion that he loves the art of rhyming. In an earlier (and rarer) conversation with Peace Magazine, Big comments on Sir Mix-a-lot (of “Baby Got Back” fame): “I wanna be just as large as those fools, but get busy, cut the bullshit… I just wanna get busy on the mic more than anything.” In 1994, he tells The New York Times he’d never move to the suburbs for fear of losing artistic inspiration—“There won’t be nothin’ to rap about except the birds”—and three years later he sits poolside in Beverly Hills, puffing a blunt and backpedaling: “[My friends] will tell me an ill story and I can build that into something. I was never one to say that all my rhymes were my exact life experiences.” Of course, that’s all they’d ever been.

These contradictions paint a more composite image of Biggie than the monolithic “King of New York” that has persisted. He was a pioneer at odds with himself, too much of a craftsman to abandon his art but too much of a hustler to compromise his funds. He is the genius that wrote “Juicy” with a frown because he wanted his first single to be “Machine Gun Funk.” And this duality is what truly makes The Notorious B.I.G’s legacy so important today: he is the pivotal intersection at which the hip-hop artist meets the hip-hop businessman (or “business, man”). Kelefa reads Puffy as the “slick businessman mourning a slain thug,” but this dichotomy gives Puff too much credit and Biggie not enough. Puff’s power came from his uncanny ability to procure talent and create spectacle, to flash the neon lights above his own head and let the world know he’s present and accounted for, not because he was a gifted record executive or producer. And Big was no clunky gangster that lived and died by the gun. He was a restless mind with plans for his own record label, clothing line, and restaurant chain. His later music was more consciously aiming at national demographics and pop charts, yet his lyrical gifts were so second nature that downplaying his skill was never considered. If Puff “[didn’t] need the money but [couldn’t] help making it” as Touré describes in a 1997 Village Voice piece, then Big didn’t need to make the brilliant music he did, but couldn’t help making it. And before he could realize it all, before his long awaited sophomore album was even released, he was shot and killed. In death he became something he never was in life: simple.

The culmination of Biggie’s internal tensions arrived on March 25, 1997, across two CDs that XXL calls “one of hip-hop’s most enduring artistic achievements.” For all its critical merit, the tragedy of Life After Death is that audiences will never be able to listen to it impartially. Besides a handful of lucky journalists who were invited to an early listening party, no one in the public heard Life After Death before Biggie was murdered, and for the few who did, its context changed dramatically immediately after. Even today, the devastating ironies of the album’s themes, artwork, titles and lyrics make it difficult to listen to in its entirety. But a close, impartial reading of the project reveals a torn and frustrated artist, working to reconcile his past triumphs and failures with what he can see so clearly and closely in his future. Where Ready To Die is brim with a white-hot pain and constant anxiety that made his street tales that much more vivid, Life After Death has a more glassy-eyed sorrow, the torment of an artist trapped between two worlds and at home in neither.

The first words we hear Big speak on the album are from the most morbid cut on Ready to Die, “Suicidal Thoughts”: “I’m sick of niggas lyin’, I’m sick of niggas hawkin/Matta fact, fuck it, I’m sick of talkin’.” We then find Big “sittin’ in the crib dreamin’ about leer jets and coups/The way Salt shoops and how to sell records like Snoop.” His dreams are interrupted when he gets word from a visitor that somebody’s gotta die, and reassures his friend: “I’m a criminal way before the rap shit… Puff won’t even know what happened.” Within the first few minutes of the album, Big has gone from death to riches, back to death and back to riches again. The record follows this pattern nearly exactly, with “Die” followed by the radio behemoth “Hypnotize,” followed by murder fantasy/broad-stroke diss record “Kick in the Door,” followed by the R. Kelly-assisted “Fuck You Tonight,” followed by the Lox-assisted “Last Day,” followed by the R&B interpolating “I Love The Dough,” and so on. It’s as if at every turn, Big has to reaffirm himself on one side or the other: it’s gritty, but it’s radio friendly, but it’s lyrical, but it’s catchy, but it’s hip-hop, but it’s R&B. There’s regional pandering (“Notorious Thugs,” “Going Back To Cali”), pop samples (“Mo’ Money, Mo Problems”) and even a few female-aimed clunkers (“Another,” “Nasty Boy”). The only constant throughout the album, in fact, is Biggie’s ambidextrous flows and deft wordplay. No matter what the marketing angle, Big still does what he does best, rhymes. It’s what defined him as an artist—as a rapper—and it’s a steadfastness that has influenced how we’d perceive his successors for years to come.

In its most popular usage among traditional rock fans, a “sell-out” is an artist that opts for major label deals, corporate endorsements and huge record sales instead of the romanticized vision of local club shows, indie distributors and general poverty. But as hip-hop has advanced and transformed, it has developed its own set of expectations for the integrity of its cultural flag bearers. Hip-hop’s purists have always measured subject and substance to parse the “real”: to this sect, those promoting positivity and consciousness in their lyrics are the genre’s true heroes, and the baseless sludge of gangsta rap and commercially-aimed dance music are everything wrong with the culture. “Out of hundreds of rap groups, the Fugees definitely represent the best,” wrote Bernard Taylor, a rap fan from New Orleans, to Vibe Magazine in 1996. “Alize and Versace references can get boring—that’s why I give the Fugees mad props. I thought I would never stop playing the Notorious B.I.G’s album Ready to Die, but after hearing The Score I pronounced Biggie Smalls dead.” Of course, within a few tragically short months, Biggie Smalls was dead, and Bernard probably wished he’d never sent that letter.

But to a larger portion of the hip-hop audience, “selling out” meant betraying the culture’s current aesthetics and energy—“watering it down” to appeal to a wider audience. A fat check from a label or a company has been seen as a victory for hip-hop ever since three kids from Hollis, Queens scored a million dollars from some Germans to wear kicks they’d have worn either way. That was the beauty of hip-hop: every shmuck with a pen and pad could reach his wildest dreams just by the veracity of his words. Biggie served to push hip-hop’s aspirations even higher: it was not only admirable to parlay a rap career into a broader corporate imprint, it was expected. In his wake, rappers saw what Big had hoped for himself, and made his dreams their reality. When he advised “stay far from timid/only make moves when your heart’s in it/and live the phrase ‘sky’s the limit’,” it was a pep talk and a plea, as much directed to his peers as it was to himself.

“I don’t want motherfuckers to just look at Big and be like, ‘Oh shit, there go Big the dope MC’,” B.I.G commented toward the end of his conversation with Chairman Mao. “I want people to look [at] Big like, ‘Look at Big. He grew. He’s a businessman now. He’s a father now. He’s taking control of his destiny. He’s movin’ up.’”  In this candid moment, the late rapper was describing his idea of success. But through Biggie’s legacy, his art, his being, we see more than just success. We see mink coats and expensive bottles, private jets and R&B bitches, caviar for breakfast and champagne bubble baths. We see the white picket fence surrounding the lawn that he dreamed of watching his daughter play on. We hear the birds he once mocked as suburban non-noise, now singing the satisfying song of stability, peace, and comfort. We see excess, and for better or worse, he made hip-hop believe that was all within its reach. That is the dream The Notorious B.I.G left us with, and because of all the greatness he gave hip-hop culture, we’ve had no choice but to try and live it all out for him.