The Beatles. Bob Dylan. Biggie Smalls.

Why the rapper belongs in the company of pop’s most influential artists.

Notorious BIG
The Notorious B.I.G., the greatest rapper who ever lived.

Photo illustration by Lisa Larson-Walker. Photo by Catherine McGann/Getty Images.

A lot of great art ends with suicide—Anna Karenina, Sgt. Pepper’s Lonely Hearts Club Band, Thelma & Louise—but it takes particular audacity to end with a suicide note. “Suicidal Thoughts,” the closing track of the Notorious B.I.G.’s towering debut album, Ready to Die, is two minutes of rhymed confession that culminates in a self-inflicted gunshot. Coming at the end of an album obsessed with death and all varieties of moral transgression, the opening lines—“when I die, fuck it I wanna go to hell / cause I’m a piece of shit it ain’t hard to fuckin’ tell”—seem to herald the most depressing piece of music in human history. But soon we have dark humor (“it don’t make sense going to heaven with the goodie-goodies / Dressed in white, I like black Timbs, and black hoodies”), deathbed sexual boasting (“My baby momma kissed me but she’s glad I’m gone / She knows me and her sister had something going on”), and cultish, kitschy references to New Jack City and Beat Street. It’s sad, funny, bleak, brilliant, and then it’s over, and all that’s left is to play the whole thing again.

Ready to Die turns 20 on Saturday, and even at a moment when hip-hop is particularly taken with such milestones, this is (fittingly) an enormous one. Ready to Die is not the greatest rap album ever made, and probably isn’t even the greatest rap album made in 1994—it sags at times with superfluous skits, some of its production touches have aged awkwardly (congrats to that whistling synth hook on “Big Poppa” for owing 20 years’ worth of royalties to The Chronic), and Sean Combs’ somnambulant hype-man routine only grows more irritating with time.

But it is quite possibly the most important, if only for the reason that its maker transformed the music like no rapper before or since. Biggie Smalls didn’t alter the hip-hop landscape so much as crater it, leaving behind an unfillable void and an unhealable wound. The Notorious B.I.G. is the greatest rapper who ever lived in the same way that Michael Jordan is the greatest basketball player who ever lived: Some people may argue but they are usually Luddite classicists, incorrigible homers, or hipster contrarians. Seventeen years after his murder at the age of 24, he is of a piece with Miles, Dylan, the Beatles, Aretha, artists whose influence is so immense it ascends into a sort of fundamental sonic iconography, the never-ending soundtrack to everything. A world without KRS-One or Ice Cube or Jay Z would be unimaginably impoverished, but a world without Biggie Smalls is simply unimaginable.

Christopher Wallace was born in Brooklyn on May 21, 1972, son of Voletta Wallace and George Letore, the latter of whom his son would barely know. Both parents were Jamaican immigrants. “Big Chris” grew up on St. James Place in the neighborhood (once) known as Bedford-Stuyvesant, and began selling drugs as an adolescent. After serving a nine-month prison stint at seventeen he redoubled his commitment to music, taking the name “Biggie Smalls,” after a character in the 1975 Sidney Poitier and Bill Cosby film Let’s Do It Again. (An ownership claim would soon force him to go by “Notorious B.I.G.” professionally.)

He made a demo with local DJ Hit Man 50 Grand that caught the ear of tastemaker Mister Cee, who in turn thrust it into the hands of Matteo Capoluongo (aka Matty C) curator of the Source magazine’s influential “Unsigned Hype” feature. In March 1992 Chris Wallace’s scowling 19-year-old visage peered out from the esteemed monthly’s pages. “Straight outta Brooklyn, New York, the heavy-set brother B-I-G has mad skills,” the column noted. “His rhymes are fatter than he is.”

The write-up grabbed the attention of an aspiring impresario named Sean “Puffy” Combs, and in spring of 1993 a solo track called “Party and Bullshit” was released on the soundtrack to the Dr. Dré (the other one) and Ed Lover vehicle Who’s the Man? The movie was quickly forgotten, but “Party and Bullshit”—initially credited simply to “BIG”—became a sensation. The song’s hook was a reworking of the Last Poets’ 1970 classic “When the Revolution Comes,” a fiery prophecy of urban revolt, which closed: “But until then you know and I know that niggers will party and bullshit and party and bullshit and party and bullshit … some might even die before the revolution comes.” Biggie snatched the phrase and iconoclastically flipped it into a club banger, the opiate becoming the end in itself—altered consciousness might be false consciousness, but it’s also the most fun consciousness. “I was a terror since the public school era / Bathroom passes, cutting classes, squeezing asses,” his voice booms in the song’s opening lines, and it’s all already there—the menace, the mischief, the mythmaking, the perfect convergences of music and language (“terror” and “era” rhyme perfectly in his Bed-Stuy patois).

By the time Ready to Die dropped on Sept. 13, 1994, the buzz surrounding the album and its maker was deafening; with his Brooklyn pedigree and growing stable of true-school endorsers, B.I.G. appeared the ordained successor to rap’s illustrious line of kings of New York. Early notices were glowing: The Source dubbed the album, with characteristic panache, an “illiotic bomb,” declaring that “each song is like another scene in his Lifestyles of the Black and Shameless, the Tec and stainless.” Even the famously rap-illiterate Rolling Stone gave it four stars.

As landmark debuts go, Ready to Die didn’t actually do a whole lot that was new. Critics praised the disturbed ambivalence with which Biggie recounted his own street hustling, but the Geto Boys’ “Mind Playing Tricks On Me” had covered the same terrain several years earlier. The storytelling was viscerally wrought and lavishly detailed, but no more so than Ice Cube’s “It Was a Good Day,” or even Slick Rick and Doug E. Fresh’s 1985 classic “La Di Da Di.” Even B.I.G.’s full-figured Casanova act, showcased on what would become the album’s biggest chart hit, “Big Poppa,” wasn’t particularly groundbreaking—Heavy D had recently worked the same shtick to great effect for Uptown Records, under the watchful gaze of Sean Combs himself.

But Ready to Die did everything bigger, and in almost every instance better. (Nothing is better than “Mind Playing Tricks On Me.”) Like his crosstown contemporary Nas, Biggie hailed from a generation raised on rap music to a degree that previous generations hadn’t been. Christopher Wallace had grown up with Run-DMC and Big Daddy Kane and Rakim, but he’d also grown up with oddball flotsam like Breakin’ 2, Disorderlies, and Kwamé, the polka-dot king. An earlier generation had come up in the period of hip-hop subculture, but Biggie’s generation came up in the period of hip-hop popular culture, an important distinction. He had total fluency within the genre and an ironic irreverence toward its past; he was aware of rap tradition while carrying himself as its culmination. “You never thought that hip-hop would take it this far,” he famously proclaimed, and there was no doubt to whom “this” referred.

When Ready to Die became a platinum-selling sensation, the hottest MC in New York was suddenly one of the biggest pop stars in the world. As blockbusters go, Ready to Die was a shockingly intimate album, and one of its most innovative aspects was its unique brand of roughneck sentimentality. The music often felt obsessively confessional, though always rendered with a dramatist’s flair. “Things Done Changed” and “Me & My Bitch” stood out as melancholic laments over bygone happiness, while “Respect” went so far as to open with a first-person retelling of the rapper’s own birth: “Umbilical cord’s wrapped around my neck / I’m seeing my death and I ain’t even took my first step.”

Even in its darkest moments—perhaps especially in its darkest moments—Ready to Die was located squarely at the intersection of personal history and personal mythmaking. Smalls’ rhymes were frequently praised for their documentary realism—“his lyrics mix autobiographical details about crime and violence with emotional honesty,” noted the New York Times in late 1994—but like most great pop music Ready to Die was primarily a work of imagination. Nowhere was this more apparent than “Juicy,” Ready to Die’s first single and its most beloved track. One fact about “Juicy” is that it is not, in any strict sense, true. While young Chris Wallace had hardly grown up in privilege, he’d been raised in a spacious three-bedroom apartment by his hard-working and accomplished mother, who by all accounts (including her own) had spoiled her son rotten—toys, video games, junk food—in her attempts to keep him away from the street-corner drug game that pocked their Bed-Stuy neighborhood. He never ate sardines for dinner in a “one-room shack,” and birthdays were certainly not the worst days.

A much more important fact about “Juicy” is that it is one of the best hip-hop tracks ever made, and maybe the greatest rags-to-riches fable in all of American music. Based around a brilliant sample of Mtume’s 1983 R&B hit “Juicy Fruit,” the song was the perfect showcase for B.I.G.’s artistry and intellect, his NYC bona fides, his monumental star power and pop charisma. For a song about how hard life once was, the track is awash in warm and lovingly referential nostalgia. The more iconic shout-outs still land—Salt-N-Pepa, Funkmaster Flex, DJ Marley Marl—but just as compelling are the moments of connoisseurship and quirky ephemera: Mr. Magic’s “Rap Attack” radio show, the World Famous Brucie B, Word Up! magazine, Shawn Brown’s colossally weird novelty track “Rappin’ Duke” (duh-ha, duh-ha).

Ready to Die was a tour de force of technique and creativity that by its end had made, and unmade, one of the most vivid characters in American popular art: the Notorious B.I.G. himself. That character was a work of staggering dimensions, physically and psychologically, a cold-blooded sociopath one minute and a brooding introvert the next, a swaggering ladykiller blessed with impossible sexual prowess, then a tragic depressive overcome by his own vulnerabilities. He drew from his own past but also from the pulp mythologies of Blaxploitation and B-list crime noirs (most notably Abel Ferrara’s King of New York), offering himself up as a pitch-dark satirization of early 1990s panics over the “superpredator.”

He was terrifying, hilarious, angry, depraved, smart as hell, harrowingly bleak, and shockingly profane. “Damn, what happened to the summertime cookouts? / Every time I turn around a nigga gettin’ took out,” he’d lament, then brag on the next track that “I’ve been robbin’ motherfuckers since the slave ships,” a line so tasteless it provokes only awe. But above of all he was likeable, incredibly so. This was the bedrock miracle of Ready to Die, how a concept album about moral nihilism and existential ambivalence somehow became a multiplatinum smash, how choruses like “fuck the world / don’t ask me for shit” came to sound as infectious as “we are the world / we are the children.” He wanted to rob you (or worse), and you almost wanted to let him, because he was the best rapper you’d ever heard in your life. The magnetism and the virtuosity were inseparable, the immense gifts of music and language paired with wit and ferocious intelligence. Take the opening to the third verse of “Everyday Struggle”: “I’m seeing body after body and our Mayor Giuliani / ain’t tryin’ to see no black man turn to John Gotti,” a line that’s disturbing and funny and ripped-from-the-headlines-current and sounds completely amazing, its soft vowels and hard consonants popping off the tongue like fireworks, or gunshots. Or, “there’s gonna be a lot of slow singin’, and flower-bringin’ / if my burglar alarm starts ringin’,” from “Warning”—never has a death threat sounded so playfully mellifluous.

Rap is sometimes described as poetry, but it’s not—it’s music. There is poetry in rap the same way that there’s poetry in folk or R&B or opera, but it exists first and foremost as sound. I can write “Buck shots out the sun roof of Lexus coupes / Leave no witnesses, what you think this is?” and it looks cool enough on the page, but it can’t convey the percussive way “buck shots” mimics the thing it’s describing, or how when rapped in a thick and husky voice that sounds like Kool G Rap meets Marlon Brando, “roof” and “coupes” sound unexpectedly beautiful together, or how “witnesses” and “think this is” rhyme perfectly even though they shouldn’t. These are the sounds of someone who heard the world differently than everyone else and who made music that bent our ears to his own—or, more simply, a musical genius. Years after the release of Ready to Die, Combs recalled how difficult it was at first to get his prized talent to even arrange his work in song form: “At first B.I.G. would write these long rhymes, like ten minutes long, with no structure, no chorus—just him destroying the microphone and leaving it smoking.”

1995 would belong to Biggie Smalls. “Big Poppa” and the DeBarge-sampling remix of “One More Chance” were radio smashes, and B.I.G. also oversaw Junior M.A.F.I.A.’s Conspiracy LP and took guest turns on its two biggest hits, “Get Money” and “Player’s Anthem,” the latter of which boasts arguably the best verse he ever recorded. He was on MTV, magazine covers, Martin. And then there was the growing rivalry with Tupac Shakur and Suge Knight’s Death Row Records, which played out in interviews, on award-show stages, and of course on record, most notably “Who Shot Ya?” the menacing masterpiece that first appeared as the B-side to “Big Poppa.” The circumstances of both Shakur’s and Biggie’s murders were horrifying at the time, and when bullets ripped through B.I.G.’s GMC Suburban on the early morning of March 9, 1997, it felt like the awful culmination of some slow-motion cataclysm. In retrospect the whole ordeal becomes all the more incomprehensible, a prolonged moment of insanity and a worst-case scenario of young men in over their heads. It will haunt the people who survived it for the rest of their lives, and likely haunt hip-hop for even longer.

Since his murder it’s become easy to hear Ready to Die as both a beginning and the beginning of the end. It’s an impression the album’s title certainly doesn’t dissuade (Biggie himself wanted to call it The Teflon Don), and there’s little question Biggie was obsessed with death and terrified by its prospect—shortly after the release of Ready to Die, he told an interviewer that he was already “scared of getting my brains blown out.” And all too predictably, in the wake of his murder his entire artistic life became reconsidered in light of his imagined trespasses. People who’d always hated rap waved bloody shirts and congratulated themselves for hating rap, and the typical hand-wringing abounded. “Rapping, Living and Dying a Gangsta Life,” one headline declared; “Which Came First, the Rapper or the Gangsta?” asked another. “The Short Life of a Rap Star, Shadowed by Many Troubles,” wrote the New York Times in a posthumous appraisal, in language eerily and sickeningly reminiscent of its controversial profile of another murdered young black man, Michael Brown, published just a few weeks ago.

The tragedy of death occasioned a referendum of the supposed pathologies of life. Christopher Wallace may have been, in the well-worn words of Nina Simone, young, gifted and black, but to many he was just a rapper, or a gangsta, if they could even distinguish between the two. Whatever forces conspired to snatch the life of an absurdly talented 24-year-old, his art form was most certainly not among them, even if few were inclined to look much further—to this day, his murder remains unsolved.

In death he became immortal. His double-album follow-up to Ready to Die was released two weeks after his murder: titled Life After Death in a morbid coincidence, it sold more than 10 million copies and begat a pair of No. 1 hits, “Hypnotize” and “Mo Money Mo Problems.” “I’ll Be Missing You,” a tribute single by Puffy and B.I.G.’s widow, Faith Evans, was released in May and spent 11 weeks on top of the Billboard Hot 100 despite being one of the worst songs ever written. Memorial shout-outs on records were so common, they began to feel like a verbal tic. By 1998 Talib Kweli was reminiscing about “when Pac and Biggie was still cool / before they was martyrs.” In 2001 Jay Z declared, “if I ain’t better than Big, I’m the closest one,” and the mere act of mentioning himself in the same sentence was gasp-inducing. For 17 years Biggie Smalls has been both ever-absent and ever-present, the singular touchstone of his genre. Genuflection is no longer even necessary, it’s just implicitly understood.

And the music endures, everywhere. In 2014 countless teenagers know every word to “Juicy,” which means that in 2014 countless teenagers at least kind of sort of know who Lovebug Starski is. If you’re under the age of 45, you probably can’t hear Diana Ross’s “I’m Coming Out” without mumbling “federal agents mad cause I’m flagrant” under your breath. The instrumental of “Who Shot Ya?” gets pumped into Nets games at the Barclays Center that stands less than a mile from Biggie’s childhood home, like some amiable and innocuous jingle for 21st-century Brooklyn. Twenty years after Ready to Die, Christopher Wallace is still the biggest star in rap, still everything he always told us he would be.