Hip-hop’s evolution since the 1990s has been nothing short of revolutionary, and it will continue to morph in countless ways. Yet, every iteration of the genre will carry the indelible DNA of The Notorious B.I.G.
Christopher Wallace, as he was born, became ground zero for many hip-hop staples we see today: the rags-to-riches narratives, the embrace of luxury brands like Versace, and the undeniable dominance of New York hip-hop on the global stage. His meteoric rise and lasting impact are all the more astounding considering he achieved it all within a mere five years in the music industry, with only one album released during his lifetime.
This is the perfect time to delve into Biggie’s tragically brief but incredibly rich discography. His work remains a gold standard in hip-hop, fueled by his unmatched charisma, lyrical dexterity, and Sean “Puffy” Combs’ impeccable ear for groundbreaking beats. Across every facet of his persona – the smooth operator, the captivating storyteller, and the master of streetwise rhymes – Biggie consistently delivered.
Here are the 25 best Notorious B.I.G. songs, including collaborations and featured appearances, that solidify his legendary status.
25. “Just Playing (Dreams)” (1993)
Biggie’s catalog is often revered with such intensity that it can overshadow his brilliant comedic timing. “Just Playing (Dreams),” initially a bonus track on the 12-inch promo for “Juicy,” is the most overt example of his playful wit. Essentially a boast rap centered around which R&B divas Biggie fantasizes about being intimate with, this two-verse gem quickly established him as one of mainstream hip-hop’s most playfully raunchy figures. The women he name-dropped – including Mariah Carey, Mary J. Blige, and the iconic Patti LaBelle – reportedly took the mentions in good humor. However, the “ugly ass Xscape bitches,” as he rhymed, were less amused. Lil’ Cease recounted to MTV News in 2012 that Biggie clarified to Xscape in Atlanta that it was all in jest.
24. “Gimme the Loot” (1994)
“Gimme the Loot” distinguishes itself as a prime example of Biggie’s signature talent for crafting vivid, cinematic narratives. This Ready to Die standout showcases B.I.G. effortlessly embodying two distinct characters. The older robber, hardened and pragmatic, views violence as merely an inconvenience (“Don’t be a jerk and get smoked over being resistant”). In contrast, his partner, with a higher-pitched, almost childlike voice, revels in the thrill of crime, akin to a kid clamoring for a Sega Genesis (“Oooooooo, Biggie let me jack her!”). The resulting shock rap pushed boundaries, with lines like “I wouldn’t give a f** if you’re pregnant” and “Bitches get strangled for their earrings and bangles” being censored even on the Ready to Die* Parental Advisory version.
23. 112’s “Only You (Remix)” feat. Mase and The Notorious B.I.G. (1996)
Bad Boy Records, a label whose 90s hits have aged remarkably well, pioneered the seamless fusion of R&B and rap. A key illustration is Atlanta R&B group 112’s Top 20 hit “Only You.” The Notorious B.I.G., already established with “Can’t You See,” showcased his smooth, melodic flow, even slipping in a Tony! Toni! Toné! reference before passing the mic. “Only You (Remix)” also marked the introduction of Bad Boy’s rising star, Mase. Mase would later dominate this honeyed lane with his own charismatic style on his multi-platinum debut album, Harlem World, in 1997.
22. “Things Done Changed” (1994)
Ready to Die signaled a profound cultural shift in hip-hop. The carefree days of “Rapper’s Delight” and neighborhood block parties were fading. The late 80s onwards brought a stark awareness of the trauma experienced by survivors of the Reagan era. “Things Done Changed,” the opening track of Ready to Die, explicitly sets this context for Biggie’s debut. “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,” Biggie raps in the poignant closing verse. In this light, the escapism found in the more celebratory tracks on Ready to Die feels not just welcome, but necessary.
21. “Warning” (1994)
“Warning,” a hook-less narrative of a thwarted robbery attempt from Ready to Die, captivates due to its conversational, almost anecdotal delivery. The details are etched in the memory like modern folklore: Word from the barbershop reaches Biggie about rivals plotting to rob him. Our protagonist is enraged (“Damn, n—as wanna stick me for my paper,” Biggie repeats in disbelief), contemplates his arsenal and means of retaliation, and ultimately dispatches the would-be robbers in a fashion that borders on dark comedy (“You got a red dot on your head too!”). Quintessential B.I.G. storytelling.
20. Junior M.A.F.I.A’s “Player’s Anthem” feat. The Notorious B.I.G. (1995)
“Player’s Anthem” transcended its initial purpose as just Junior M.A.F.I.A.’s debut single, becoming a genuine anthem for players worldwide. This collective, comprised of Biggie’s childhood friends from Bedford-Stuyvesant, benefited immensely from forming during the pre-Life After Death era. This period saw Biggie effortlessly contributing to numerous hits, including even a collaboration with Michael Jackson. “Player’s Anthem,” with its lush production by DJ Clark Kent, also marked the first single appearance of Lil’ Kim. Her now-iconic, sneering delivery was fully formed right from the beginning.
19. “One More Chance (Remix)” feat. Faith Evans and Mary J. Blige (1995)
The original “One More Chance” is so sexually explicit, it’s hardly suitable for public playback. Preceded by the overtly pornographic “F** Me (Interlude)” skit, this version is a cartoonishly obscene sex rap, rivaling even 2 Live Crew in its explicitness. Yet, Diddy recognized radio potential and, in a stroke of genius, enlisted producer Rashad Smith to rework the track for a remix. Smith recounted to REVOLT* in 2017 that his initial sample was Ohio band Faze-O’s “Riding High.” Unsatisfied, he switched to the instantly recognizable sample of DeBarge’s “Stay With Me.” Diddy wisely brought in Mary J. Blige for backing vocals and Faith Evans, whose yearning hook performance became the perfect counterpoint to her husband’s laid-back charisma.
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 the titans of New York hip-hop. However, Biggie was initially skeptical of the future king. “I’m warning [Biggie] like, ‘My guy is coming… He don’t write rhymes,’” “Brooklyn’s Finest” producer DJ Clark Kent shared with SPIN in 2016. “Get the f*** 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 quickly discovered DJ Clark Kent wasn’t exaggerating. “Brooklyn’s Finest” became a phenomenal back-and-forth, pitting a young, hungry Jay-Z against Brooklyn’s reigning champion. Biggie, despite being embroiled in conflict, still managed to inject humor (“If Fay’ had twins, [she’d probably have two Pacs]/ Get it?”). After Biggie’s passing the following year, “Brooklyn’s Finest” came to symbolize a passing of the torch moment in hip-hop history.
17. Puff Daddy’s “Victory” ft. The Notorious B.I.G. and Busta Rhymes (1998)
Released a year after his death, “Victory” presents Biggie in a ghostly, spectral form. A departure from No Way Out‘s earlier, more upbeat singles, “Victory” is anchored by the somber brass from Bill Conti’s “Going the Distance” from the Rocky film series. In one of Bad Boy’s most powerful moments, Puff Daddy unearthed Biggie verses that resonate with the ominous tone that permeated Life After Death. B.I.G. concludes his second verse, one of his final recordings, by shouting out his Bad Boy crew and possibly referencing The Commission, a rumored supergroup involving Puff and Jay-Z. Tragically, this exciting prospect died with Biggie.
16. Junior M.A.F.I.A.’s “Get Money” (1995)
Lil’ Kim undeniably emerged as the biggest solo star from Junior M.A.F.I.A. outside of Biggie himself. Therefore, it’s fitting that one of the group’s essential tracks is her duet with Biggie, “Get Money.” Notably, Biggie – whose verse addresses a lover’s betrayal (echoing his earlier “Warning” sentiment: “Damn, why she wanna stick me for my paper?”) – takes a backseat as Lil’ Kim assumes the dominant role. Her verse is packed with NSFW one-liners (“Deeper than the pussy of a bitch six feet”), foreshadowing her evolution towards even more explicit lyrics, such as “[Got buffoons eating my pussy while I watch cartoons].”
15. Total’s “Can’t You See?” ft. The Notorious B.I.G. (1995)
A key factor in Bad Boy’s seamless blend of R&B and rap was that both genres drew inspiration from shared musical foundations. When artists grow up immersed in a particular form of expression, it subconsciously shapes their worldview. Total’s classic “Can’t You See” exemplifies this, minimizing the funk of James Brown’s “The Payback” to create a silky smooth soundscape. Despite his crass opening lines (“Give me all the chicken heads from Pasadena to Medina”), Biggie’s collaboration with Total feels like destiny, yet another testament to Sean Combs’ hit-making instincts. Diddy’s ad-libbed response, “slow down son, you’re killing ’em,” has become an iconic, oft-quoted element of this club staple.
14. “I Got a Story to Tell” (1997)
Life After Death saw Biggie intensifying his noirish storytelling raps (“N—as Bleed,” “Somebody’s Gotta Die”), but “I Got a Story to Tell” stands as the most unforgettable. In this track, B.I.G. recounts an after-hours encounter with a woman involved with a New York Knicks player, who happens to be playing against the Utah Jazz that very night. This player – described as around 6-foot-5, Biggie isn’t certain – unexpectedly walks in, forcing our anti-hero to rob him. Biggie then dedicates the latter half of the track to recounting this unbelievable tale to his friends in a barbershop setting (“Y’all n—as ain’t gonna believe what the f*** happened to me”). The narrative is so absurdly detailed, it’s hard to dismiss it as pure fiction.
And, surprisingly, it wasn’t. Fat Joe reluctantly revealed to ESPN in 2016 that the athlete in question was the late Knicks fan favorite Anthony Mason, a claim Diddy confirmed a few days later. Even at his most outlandish, Biggie’s raps often mirrored his reality.
13. Mary J. Blige’s “Real Love (Remix)” ft. The Notorious B.I.G. (1992)
While he shone brightest as a solo star, Biggie Smalls was also a remarkably effective hype man. In his second most essential pre-Ready to Die appearance, B.I.G. injected his signature wit right from the opening lines, 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 release his debut solo single, “Party and Bullshit,” the following year, but it couldn’t quite reach the euphoric, new jack swing heights of this remix.
12. “Sky’s the Limit” ft. 112 (1997)
DJ Clark Kent disclosed to BET in 2017 that the beat for “Sky’s the Limit” was not initially intended for Biggie. “When he heard ‘Sky’s The Limit,’ I was like, well this track is for [Akinyele] so you can’t have it,” the producer explained. “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.’”
Consequently, DJ Clark Kent held onto it for two years before it became the inspirational centerpiece of Life After Death. “Sky’s the Limit” is, in many ways, the spiritual successor to “Juicy.” The poignant difference is that “Sky’s the Limit,” released posthumously, serves as a memorial to dreams already realized. The music video – featuring child actors portraying the Bad Boy crew reveling in luxury – added a touch of innocent sentimentality.
11. Funkmaster Flex’s “Live Freestyle” ft. The Notorious B.I.G. and Tupac Shakur (1993)
While canonized on Funkmaster Flex and Big Kap’s 1999 album The Tunnel, the iconic freestyle featuring B.I.G. and Tupac Shakur actually occurred several years prior. The two performed these verses alongside hip-hop legends Big Daddy Kane and rising star Shyheim at the 1993 Budweiser Superfest, a Madison Square Garden extravaganza that also included Patti Labelle and Bell Biv DeVoe. Renowned New York DJ Mister Cee, who recorded the moment, recalled to MTV that while Notorious B.I.G. had generated buzz with “Party and Bullshit,” Tupac was the bigger star, fresh off the release of Poetic Justice starring Janet Jackson. Decades later, however, it’s difficult to find a New York DJ willing to play Tupac’s verse after Biggie’s, whose unforgettable “WHERE BROOKLYN AT?” has become a rallying cry for the borough.
10. “I Love the Dough” ft. Jay-Z (1997)
The sheer scope of Life After Death was so vast that a potential single like “I Love the Dough” ended up as just an album cut. JAY-Z and Biggie’s follow-up to “Brooklyn’s Finest” adopted a more traditional song structure with complete verses and a proper hook, but its extravagance was anything but ordinary. Hov delivers quotable lines (“Skip the bull ‘cause we matadors”; “Being broke is childish and I’m full grown”), while Biggie mesmerizes with intricate internal rhymes (“Blind your broke asses, even got rocks in the beards and moustaches”). A highlight of Jay-Z’s 4:44 Barclays Center tour stop was when he resurrected this track for a rare live performance.
9. “Ten Crack Commandments” (1997)
This track also wasn’t originally intended for Biggie. DJ Premier told the late Combat Jack in 2013 that the beat was created for fellow New York emcee Jeru the Damaja. The instrumental was also used for Angie Martinez’s “Top 5 at 9” segment on Hot 97. Puff Daddy heard it one night and requested it for The Notorious B.I.G.’s album. As a result, the Chuck D sample is now instantly recognizable as the intro to hip-hop’s most famous rulebook. Lin-Manuel Miranda famously adapted this Life After Death highlight into the “Ten Duel Commandments” for Hamilton, while Faith Evans reinterpreted it as the “[Ten Wife Commandments].”
8. “Big Poppa” (1994)
“Big Poppa” is another example of Puff Daddy softening Biggie’s raw street edge for mainstream appeal. Ready to Die‘s second major single features the Bad Boy icon gliding over the Isley Brothers’ 1983 classic “Between the Sheets.” It’s undeniably a calculated move for Top 10 success, but Biggie’s slow jam unveils a world of grandeur and lust that’s as expansive as the legendary restaurant tracking shot in Goodfellas. “Big Poppa” paints a vivid picture in a way few rappers could replicate, and by the time Notorious B.I.G. finishes his endearingly off-key hook, he has firmly established himself as a legitimate sex symbol.
7. “Unbelievable” (1994)
Ready to Die was nearing completion when Biggie convinced DJ Premier to create this beat for a mere $5,000. As he would later do with Jay-Z, Premier’s sample-heavy style provided an immediate bridge between commercial ambition and street credibility. For Biggie, the dark, carnival-esque sounds of “Unbelievable” served precisely that purpose. Notorious B.I.G. distills the most crucial aspects of his persona into the album’s most aggressive set of rhymes. The opening lines – ”Live from Bedford-Stuyvesant, the livest one/ Representing BK to the fullest” – have become Bedford-Stuyvesant’s most cherished slogan; no amount of gentrification can erase that legacy. Even as Ready to Die balanced Top 40 aspirations with hardcore hip-hop, the placement of “Unbelievable” as the penultimate track underscored that Biggie was, first and foremost, a true rapper.
6. “Who Shot Ya?” (1994)
Diddy and B.I.G. consistently denied that this song was about Tupac, with Biggie stating it was recorded months before Tupac was shot and robbed in the lobby of the very studio where they were recording. However, the song was released a month after the incident, and Tupac was convinced it was a deliberate setup. The feud was irrevocably ignited.
“Who Shot Ya?” became a pivotal point in a chain of events with tragic consequences for both artists. It’s impossible to separate that context from what is, in itself, a surreal and chilling track. Producer Nashiem Myrick’s deceptively sweet use of David Porter’s “I’m Afraid The Masquerade Is Over” lends the track a psychedelic eeriness. Biggie, more menacing than ever, utilizes negative space in his verses, amplifying the biblical weight of his threats (“Feel a thousand deaths when I drop ya/ I feel for you”).
Regardless of whether Biggie’s lines were aimed at him, Tupac perceived them as a direct attack and retaliated in kind following his 1995 prison sentence stemming from a 1993 sexual assault case. “Hit ‘Em Up” explicitly named Biggie, Puff, and Bad Boy, solidifying its place as hip-hop’s most venomous diss track decades later.
5. “Mo Money Mo Problems” ft. Mase and Puff Daddy (1997)
Biggie spends much of Life After Death contemplating the darker side of excess, but he momentarily transforms that anxiety into pure joy with Mase and Puff on “Mo Money Mo Problems.” While everyone involved embraces the “get money” mantra, the concept never overshadows their individual personalities. Mase is so self-absorbed, he doesn’t even finish his verse before the hook kicks in. The Notorious B.I.G. still maintains a foot in the criminal underworld (“Me lose my touch? Never that/If I did, ain’t no problem to get the gat”) and at least one wrist adorned with Rolexes. But ultimately, it’s all about that infectious Diana Ross sample – a beam 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” serves as the ultimate trump card in any “Notorious B.I.G. as GOAT” debate, unequivocally demonstrating his technical versatility. He seamlessly adapted his typically relaxed flow to match Bone Thugs-n-Harmony’s famously intricate double-time delivery. And Biggie sounded completely at home – his signature cinematic detail permeates the rapid-fire verse, creating a thriller-like atmosphere as the song transitions from opulence to violence. Bonus points if you can rap Bizzy Bone’s dizzying verse verbatim.
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 provided Bad Boy Records with its first hit, the Platinum-selling “Flava in Ya Ear.” However, this auspicious start to Puff Daddy’s empire ironically marked the beginning of Craig Mack’s decline. With the remix, “Flava in Ya Ear” arguably became Biggie’s song in a matter of seconds. “You’re mad ’cause my style you’re admiring/Don’t be mad, UPS is hiring” is the immortal couplet, but almost every line is a ruggedly delivered gem. This performance showcased Biggie’s ability to create iconic moments even from seemingly nonchalant verses, and “Flava in Ya Ear (Remix)” solidified Biggie as Bad Boy’s undeniable future.
2. “Hypnotize” (1997)
Life After Death saw Notorious B.I.G. evolve from street survivalist to mafioso storyteller, often depicted behind Versace shades. “Hypnotize” served as the introduction to Biggie’s nouveau riche era, making Bad Boy’s choice of relatively minimalist production, by their standards, feel bold. The groove-laden bassline and echoing guitar riff – sampled from Herb Alpert’s “Rise” – subtly frame the larger-than-life persona of Biggie, who effortlessly exuded sex appeal, danger, and dark humor. It’s also propelled by a flow whose acrobatic nature contrasts with his famously robust physique. The Paul Hunter-directed music video features a high-speed chase culminating in Puff and Biggie sailing into the sunset on a boat in triumph. It’s a cliché that carries poignant weight: Biggie did not live to see the final edit of the video.
1. “Juicy” (1994)
The Notorious B.I.G. reportedly wasn’t initially enthusiastic about creating what would become his most beloved hit. He apparently envisioned Ready to Die as a showcase for hardcore East Coast rap and required persuasion from Puff Daddy to explore other sounds. The Bad Boy mogul’s intuition to have his star artist rhyme over Mtume’s sensual funk & B hit “Juicy Fruit” demonstrates his impeccable commercial instincts, while the subsequent ubiquity of “Juicy” cements Biggie’s artistic genius.
Ready to Die did produce higher-charting hits in “Big Poppa” and “One More Chance Remix,” which both peaked after “Juicy” reached No. 27. But “Juicy” holds a special place because it resonates deeply with people’s personal narratives in a way few other songs can. 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” gain profound resonance when you recognize they’ve become interwoven with countless personal stories. “Juicy” is an exaggerated autobiography, but it’s also the story of hip-hop itself and how its legends reshape the American Dream through sheer talent and determination.
