Hip-hop has transformed dozens of times in the decades since the ‘90s, and will change dozens of more times in the years to come. That said, there won’t be a permutation of the genre that doesn’t carry The Notorious B.I.G.’s DNA.
He’s ground zero for many of today’s tropes, including the started-from-the-bottom narratives, that love of Versace, and the mainstream power of New York hip-hop. Every birthday is a reminder that the man born Christopher Wallace was able to accomplish all of this in just five years in the business and one album released in his lifetime.
This time of year is also for once again taking stock of Biggie’s tragically short catalog. Sifting through it, a lot of his material still stands as some of the best hip-hop has to offer, thanks to the charisma that naturally leaks out of his prose, as well as Sean “Puffy” Combs’ pristine ear for beats. That goes for every dimension of Biggie’s persona — the certified mack, the raconteur, and the English language-loving street rhymer.
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Here are the Notorious B.I.G.’s best 25 songs, including collabs and featured appearances.
25. “Just Playing (Dreams)” (1993)
The decades of intense idolatry surrounding Biggie’s catalog sometimes overlook that his best material often hung on his comedic wit. “Just Playing (Dreams),” an add-on to the 12-inch promo for “Juicy,’ stands as his catalog’s most obvious example. Essentially a boast rap about which R&B singers Biggie wants to have sex with, the two-verse favorite showed early on he’d become one of mainstream hip-hop’s most ribald stars. The stars he name-checked — including Mariah Carey, Mary J. Blige, and ‘70s/’80s star Patti LaBelle — all supposedly took the mentions in stride. The women who did take issue, somewhat understandably, were the “ugly ass Xscape bitches.” “We saw them in Atlanta and Big explained to them that it was all in fun,” friend Lil’ Cease told MTV News in 2012.
24. “Gimme the Loot” (1994)
“Gimme the Loot” stands out because it’s one of the more animated examples of Biggie’s signature knack for vivid details. The Ready to Die fan favorite finds B.I.G. effortlessly giving his two characters definition: The older robber is the kind of guy who sees murder as an inconvenience (“Don’t be a jerk and get smoked over being resistant”), while his helium-voice partner takes joy in crime the same way a child might beg for a Sega Genesis (“Oooooooo, Biggie let me jack her!”). The resulting shock raps were too much: The lines “I wouldn’t give a fuck if you’re pregnant” and “Bitches get strangled for their earrings and bangles” were even censored on Ready to Die’s Parental Advisory version.
23. 112’s “Only You (Remix)” feat. Mase and The Notorious B.I.G. (1996)
One of the biggest innovations of Bad Boy — a label whose ‘90s hits have aged better than songs decades their junior — was how its biggest hits presented R&B and rap as two naturally complementing flavors. A key example was Atlanta R&B quartet 112’s Top 20 hit “Only You.” The Notorious B.I.G., already with “Can’t You See” under his belt, was still in his mellifluous pocket, slipping in a Tony! Toni! Toné! reference before ceding the floor. “Only You (Remix)” was also significant for introducing many to Bad Boy labelmate Mase, who’d go on to run this honeyed lane with his own brand of charisma on his 1997 multi-platinum debut, Harlem World.
22. “Things Done Changed” (1994)
Ready to Die was another example of a cultural sea change in hip-hop. The good times of “Rapper’s Delight” and peace-keeping block parties were gone; from the late ‘80s onward, we’d become familiar with the trauma of the Reagan era’s survivors. “Things Done Changed,” Ready to Die’s first song, explicitly lends Biggie’s debut this context. “Damn, what happened to the summertime cookouts/ Every time I turn around a n—a getting took out/ Shit, my Momma got cancer in her breast/ Don’t ask me why I’m motherfucking stressed,” raps Biggie in the closing bars. With this, the escapism of Ready to Die’s highs feel necessary.
21. “Warning” (1994)
Ready to Die’s hook-less recounting of a foiled robbery works because of the conversational way it unfolds. The details stick in your mind like modern folklore: Pop from the barbershop informs Biggie that foes are planning to rob him; our hero gets pissed (“Damn, n—as wanna stick me for my paper,” Biggie repeats four straight times in disbelief), spends a few bars musing about all the means he has to vanquish these villains, before finally doing away with them in a borderline slapstick manner (“You got a red dot on your head too!”). Classic B.I.G.
20. Junior M.A.F.I.A’s “Player’s Anthem” feat. The Notorious B.I.G. (1995)
“Player’s Anthem” became an actual player’s anthem, despite it being only Junior M.A.F.I.A’s first single. Composed of Biggie’s friends from his Bed-Stuy neighborhood, the debuting clique benefitted from forming in that pre-Life After Death timeline that featured the rapper sliding into numerous hits (and even a Michael Jackson song). Plushly produced by DJ Clark Kent, “Player’s Anthem” was also the first appearance on a single from Lil’ Kim. The sneering delivery that became her signature was present from the jump.
19. “One More Chance (Remix)” feat. Faith Evans and Mary J. Blige (1995)
The original “One More Chance” is the reason you can’t really play Ready to Die straight through in public. Preceded by the pornographic “Fuck Me (Interlude)” skit, this edition is a cartoonishly obscene sex rap rivaled only by the 2 Live Crew. Still, Diddy saw something radio-worthy in it — and in one of his frantic strokes of genius, called up producer Rashad Smith to chop up a sample for the remix. Smith told REVOLT in 2017 that he originally chopped up the Ohio band Faze-O’s “Riding High,” but not quite satisfied, he switched it up for the instantly recognizable sampling of DeBarge’s “Stay With Me.” Diddy wisely corralled Mary J. Blige for supporting vocals, as well as Faith Evans, whose yearning performance on the hook became the perfect foil for her husband’s lounging presence.
18. JAY-Z’s “Brooklyn’s Finest” ft. The Notorious B.I.G. (1996)
JAY-Z and the Notorious B.I.G. are now recognized as New York hip-hop’s biggest towers, but the latter was skeptical of the future king at first. “I’m warning [Biggie] like, ‘My guy is coming… He don’t write rhymes,’” “Brooklyn’s Finest” producer DJ Clark Kent told SPIN in 2016. “Get the fuck outta here. I’m like, ‘No, he don’t write rhymes. He usually gets it in one take. He ain’t gotta do his verses over.’”
Biggie found out DJ Clark Kent wasn’t bluffing. “Brooklyn’s Finest” became a stunning back-and-forth that found a young and hungry Jigga matching wits with Brooklyn’s champion, who still could crack a smile despite being locked in a war (“If Fay’ had twins, she’d probably have two Pacs/ Get it?”). After Biggie’s death the following year, “Brooklyn’s Finest” came to represent a passing of the baton.
17. Puff Daddy’s “Victory” ft. The Notorious B.I.G. and Busta Rhymes (1998)
Arriving a year after he died, “Victory” finds the Black Frank White returning as a grim apparition. “Victory” was a stark contrast to No Way Out’s prior jiggy-era singles, centering around the grave brass of Bill Conti’s “Going the Distance” from the Rocky series. In one of the Bad Boy catalog’s most world-beating highlights, Puff grabs a pair of Biggie verses that are very much shrouded in the foreboding tone that ended Life After Death. B.I.G. ends his second verse, one of the last he ever recorded, by shouting out his Bad Boy crewmates and possibly referring to the Commission, a supergroup said to include Puff and Jay-Z. Sadly, that exciting possibility died with B.I.G.
16. Junior M.A.F.I.A.’s “Get Money” (1995)
Lil’ Kim was by far the biggest non-Biggie star of the Junior M.A.F.I.A. clique, so it makes sense one of the group’s few essentials is her duet with Biggie. Notably, Biggie — who spends his verse shaking off his girl’s betrayal (echoing his earlier “Warning” lament: “Damn, why she wanna stick me for my paper?”) — takes the backseat here as Lil’ Kim becomes the player. Her verse features a barrage of NSFW one-liners (“Deeper than the pussy of a bitch six feet”), which shows the leap from here to “Got buffoons eating my pussy while I watch cartoons” wouldn’t be far.
15. Total’s “Can’t You See?” ft. The Notorious B.I.G. (1995)
A big reason why Bad Boy’s blend of R&B and rap was so seamless is how both sides drew inspiration from the same source material. When you’ve spend your formative years engaging in one form of expression, it at least subconsciously becomes part of your worldview. A result is Total’s classic “Can’t You See,” which minimizes the funk of James Brown’s “The Payback” to create aural silk. Even with his crass opening lines (“Give me all the chicken heads from Pasadena to Medina”), Biggie’s pairing with Total comes across as an act of kismet, though it’s really another example of Sean Combs’ ear for hits. Diddy’s cackling one-liner in response, “slow down son, you’re killing ‘em,” has also became an oft-quoted part of this club standard.
14. “I Got a Story to Tell” (1997)
Life After Death saw Biggie doubling down on noirish storytelling raps (“N—as Bleed,” “Somebody’s Gotta Die”), but the most indelible of the bunch is “I Got a Story to Tell.” In this episode, B.I.G. has an after-hours tryst with a woman who happens to be involved with a player from the Knicks, who’s playing against the Utah Jazz that night. This fellow — who’s about 6-foot-5; Biggie’s not entirely sure — walks in at the wrong time, forcing our anti-hero to rob him. Biggie then spends the latter half of the track retelling the tale to his boys in a barbershop-like conversation (“Y’all n—as ain’t gonna believe what the fuck happened to me”). The whole saga is too absurdly detailed to not at least have some truth to it.
And apparently it did: Fat Joe reluctantly told ESPN in 2016 that the victim in question was late Knicks fan favorite Anthony Mason, and Diddy confirmed a few days later. Even at their most bizarre, Biggie was really living his raps.
13. Mary J. Blige’s “Real Love (Remix)” ft. The Notorious B.I.G. (1992)
Though he worked much better as a star, Biggie Smalls was a pretty solid hype man as well. In his second-most essential pre-Ready to Die appearance, B.I.G. made his slick humor known in his opening lines as he was toasting his future Bad Boy labelmate: “Look up in the sky It’s a bird, it’s a plane/ Nope, it’s Mary Jane, ain’t a damn thing changed.” Biggie would finally release his debut solo single, “Party and Bullshit,” the next year, but it didn’t come close to matching this remix’s euphoric, new jack swing heights.
12. “Sky’s the Limit” ft. 112 (1997)
DJ Clark Kent told BET in 2017 that the beat for “Sky’s the Limit” wasn’t even Biggie’s at first. “When he heard ‘Sky’s The Limit,’ I was like, well this track is for Akinyele so you can’t have it,” the producer said. “He’s like, ‘Nah,’ I need that. I said, ‘Not for Junior M.A.F.I.A.!’ He’s like, ‘Nah, that’s for my album.’
So, DJ Clark Kent sat on it for two years before it became Life After Death’s inspirational testimony. “Sky’s the Limit” is the spiritual cousin of “Juicy” in a lot of ways; the bittersweet difference is how the former, released after Biggie’s death, is a memorial of dreams already lived. The video — which featured Bad Boy’s kiddie counterparts frolicing in largesse — was an innocently sentimental touch.
11. Funkmaster Flex’s “Live Freestyle” ft. The Notorious B.I.G. and Tupac Shakur (1993)
Though it’s canonized in Funkmaster Flex and Big Kap’s 1999 album The Tunnel, B.I.G. and Tupac’s famous freestyle happened several years earlier. The two performed the verses alongside fellow legend Big Daddy Kane and rap prodigy Shyheim at 1993’s Budweiser Superfest, a Madison Square Garden extravaganza that also featured Patti Labelle and Bell Biv DeVoe. Renowned New York DJ Mister Cee, who recorded the moment, recalled to MTV that while the Notorious B.I.G. had some buzz after releasing “Party and Bullshit,” Tupac was the star, because the Janet Jackson-starring Poetic Justice had just come out. Of course, a few decades later, you’d be hard pressed to find a New York DJ willing to play through Tupac’s impassioned verse after Biggie’s, whose impossibly iconic “WHERE BROOKLYN AT?” has grown to become Brooklyn’s warcry.
10. “I Love the Dough” ft. Jay-Z (1997)
Life After Death scope was so grand that a clear single like “I Love the Dough” was relegated to being an album cut. JAY-Z and Biggie’s follow-up to “Brooklyn’s Finest” was more traditionally structured with full verses and an actual hook, but the flashiness was far from standard. Hov throws in some excellent quotables (“Skip the bull ‘cause we matadors”; “Being broke is childish and I’m full grown”), while Biggie intoxicates with sharp internal rhymes (“Blind your broke asses, even got rocks in the beards and moustaches”). One of the best moments of Jay-Z’s 4:44 Barclays Center tour stop was when he revived this cut for a rare live rendition.
9. “Ten Crack Commandments” (1997)
This song wasn’t originally Biggie’s either: DJ Premier told the late Combat Jack in 2013 that beat belonged to fellow New York emcee Jeru the Damaja. The instrumental was also used for Angie Martinez’s “Top 5 at 9” Hot 97 show. Puff Daddy tuned in one night and requested it for the Notorious B.I.G.’s album. As a result, the Chuck D sample is now recognizable as the intro to hip-hop’s most cited rulebook. Lin-Manuel Miranda would turn the Life After Death highlight into the “Ten Duel Commandments” for Hamilton, while Faith Evans re-envisioned it as the “Ten Wife Commandments.”
8. “Big Poppa” (1994)
“Big Poppa” is another example of Puff Daddy smoothing out the edges of Biggie’s street-honed grit. Ready to Die’s second big single features the Bad Boy star bouncing along to Isley Brothers’ 1983 classic “Between the Sheets.” It’s clearly a shameless reach for the Top 10, but Biggie’s slow jam unveils his world’s grandeur and lust that’s as widescreen as Goodfellas’ legendary restaurant tracking shot. “Big Poppa” is picturesque in a way other rappers could not duplicate, and by the time the Notorious B.I.G. finishes singing his joyously off-key hook, he’s already solidified himself as a legitimate sex symbol.
7. “Unbelievable” (1994)
Ready to Die was wrapping up its recording sessions when Biggie had to convince DJ Premier to concoct this beat for just $5,000. Like he’d later do with Jay-Z, Premier’s sample-heavy style is an immediate throughway from commercial ambitious to street realness. For Biggie, the dark, carnivalesque boops that buoyed “Unbelievable” served that purpose. Notorious condenses the most essential aspects of his persona into the album’s most pugilistic set of rhymes. The opening bars — ”Live from Bedford-Stuyvesant, the livest one/ Representing BK to the fullest” — has gone on to become the neighborhood’s most treasured calling cards; no sprung-up coffee shops since will erase that. Even as Ready to Die balanced Top 40 radio ambition and concrete hip-hop, the placement of “Unbelievable” as its penultimate song argued that Biggie was a straight-up rapper first.
6. “Who Shot Ya?” (1994)
Diddy and B.I.G. denied this song was about Tupac, with the latter saying it was recorded months before he was shot and robbed at the lobby of the same studio they were recording in. But the song dropped a month after the incident, and Tupac was convinced they’d set him up. The die was cast.
“Who Shot Ya?” would be part of a chain of events with fatal consequences for both sides, and it’s impossible to divorce that context from what’s by itself a surrealistically sharp track. Producer Nashiem Myrick’s deceptively candied use of David Porter’s “I’m Afraid The Masquerade Is Over” lends the missive a psychedelic quality. Biggie, menacing as ever, makes use of negative space in his verses that give his threats a biblical intensity (“Feel a thousand deaths when I drop ya/ I feel for you”).
Regardless of whether Biggie’s lines were targeting him, Tupac now saw him as a foe and would respond in kind following his 1995 prison sentence stemming from a 1993 sexual assault case. “Hit ‘Em Up” did mention Biggie, Puff, and Bad Boy by name, in what remains hip-hop’s most vicious diss track decades later.
5. “Mo Money Mo Problems” ft. Mase and Puff Daddy (1997)
Biggie spends much of Life After Death ruminating on the dark consequences of excess, but he does take a moment to subvert that stress into joy with Mase and Puff’s help on “Mo Money Mo Problems.” Though all involved subscribe to the get-money ethos, the concept never overshadows their individuality. Mase is so self-obsessed, he doesn’t bother finishing his verse before the hook. The Notorious B.I.G. still has one foot in crime (“Me lose my touch? Never that/If I did, ain’t no problem to get the gat”) and at least one wrist in Rollies. But it’s ultimately all about that Diana Ross sample — a ray of light that reflects off those shiny suits and continues to radiate decades later.
4. “Notorious Thugs” ft. Bone Thugs-n-Harmony (1997)
“Notorious Thugs” is the trump card for every Notorious B.I.G.-as-GOAT debate because it’s the most resounding proof of his technical versatility. He swapped out of his typically laid back flow to Bone Thugs-n-Harmony’s famously complex double time. And Biggie didn’t feel at all out of his element — his signature love of cinematic detail imbues itself in the rapid fire verse, evoking a thriller sensibility as it descends from decadence to violence. Bonus points if you know Bizzy Bone’s dizzying verse by heart.
3. Craig Mack’s “Flava in Ya Ear (Remix)” ft. The Notorious B.I.G., Rampage, Busta Rhymes, Puff Daddy, and LL Cool J (1994)
The late Craig Mack gave Bad Boy Records its first hit with the Platinum-selling “Flava in Ya Ear.” However, the auspicious start to Puff Daddy’s dynasty ended up becoming the beginning of the end for the Craig. With the remix, “Flava in Ya Ear” became Biggie’s song in a few decisive seconds. “You’re mad ’cause my style you’re admiring/Don’t be mad, UPS is hiring” is the immortal couplet here, but nearly every bar is a ruggedly delivered quotable. The performance was a showcase in how the Notorious B.I.G. could spin moments even out of his most laconic sentiments, and “Flava in Ya Ear (Remix)” made it clear Biggie was Bad Boy’s future.
2. “Hypnotize” (1997)
Life After Death saw the Notorious B.I.G. graduating from street survivalism to mafioso narratives told behind Versace shades. “Hypnotize” was the introduction to Biggie’s nouveau riche era, which is why it feels brave that the Bad Boy chose production that’s minimal by the label’s standards. The groove-laden bassline and echoing guitar slap — cribbed from Herb Alpert’s “Rise” — shimmy around the outsizedness of Biggie’s persona, which slickly exuded sex, mayhem, and dark wit with equal efficacy. And it helps that it all rides atop a flow whose acrobatics juxtapose with his proudly rotund figure. The Paul Hunter-directed video features a high-speed chase that ends with Puff and Biggie riding a boat into the sunset in triumph. It’s a cliche that rings poignant: Biggie didn’t live to see the video’s final edit.
1. “Juicy” (1994)
The Notorious B.I.G. didn’t really care for doing what would become his most beloved hit. He apparently wanted Ready to Die to center on hard-edge East Coast rap and needed some convincing from Puff to do otherwise. That the Bad Boy mogul got the idea to have his main attraction rhyme over Mtume’s sensual funk & B hit “Juicy Fruit” speaks to his impeccable commercial ear, while the resulting ubiquity of “Juicy” speaks to Biggie’s genius.
Ready to Die did birth higher charting hits in “Big Poppa” and “One More Chance Remix,” which both broke after “Juicy” peaked at No. 27. But “Juicy” is special because of how it burrows itself in people’s biographies in a way few other songs could. There’s a tender intimacy in lines like “Super Nintendo, Sega Genesis/When I was dead broke, man, I couldn’t picture this” and “No heat, wonder why Christmas missed us Birthdays was the worst days” rings truer when you realize they’ve become part of everyone’s stories. “Juicy” is an exaggerative biography, but it’s also the tale of hip-hop and how its legends bend the American Dream through sheer genius.