Can you believe it’s been twenty years since The Notorious B.I.G. was murdered? In a career that barely spanned half a decade, the MC born Christopher Wallace blessed us with more classics than can be held on one playlist. Boasting vivid storytelling skills, a nimble, versatile flow, and a sense of wit and humor that’s not discussed enough when discussing his legacy, Biggie combined the best traits of Slick Rick, Big Daddy Kane and Rakim to create a style that cements him as one of the five best rappers to ever grace a microphone* (and in my opinion, the most skilled emcee not named Rakim).

Here’s a list of his 25 best songs/guest appearances. As you’ll be able to see, Biggie had a knack for upstaging any rapper he recorded with, and this was usually with the knowledge that his collaborators had to step their game up to compete. For someone with a ridiculously small catalog, I can easily list another 10 songs with memorable B.I.G. performances-including guest appearances alongside Neneh Cherry, R. Kelly, Michael Jackson, and 112.

Pour one out for Brooklyn’s finest and marvel at the lyrical supremacy exhibited on these songs (with two entries not available on Spotify, unfortunately.)

l. Who Shot Ya? (B-side of “Big Poppa” single, 1994)
From a production standpoint, “Who Shot Ya?” is clearly a Wu-Tang rip. The sharp keys, the moaning background vocals-B.I.G. (or, more accurately, his producers) clearly took notes from the RZA (and the Wu-Tang team noticed, clapping back at Biggie a few times.) Lyrically, though? “Who Shot Ya?” is ALL Christopher Wallace. The keys aren’t the only thing icy on this record. B.I.G. delivers his verses with a level of calm that becomes almost disconcerting when you discover what he’s talking about. There are problematic elements to most of B.I.G.’s verses with twenty-something years retrospect, but the fact that (in most cases) those issues can be overlooked is a testament to his talent. Although I still have quite a bit of trouble listening to the conclusion of the original song, which culminates in gunfire. And, by the way, I don’t think “Who Shot Ya?” is about 2Pac, either.
2. “Flava In Ya Ear” (from the single, 1994)**
Craig Mack must have been sad after realizing that he was upstaged on his own song by at least two, possibly three emcees. And his verse was actually pretty good! However, Bad Boy’s first artist was no match for a gibberish-spewing L.L. Cool J, or a more unhinged than usual Busta Rhymes, who delivered the second-best guest verse of his career and STILL got bested by Biggie. Referencing the never-seen “Diff’rent Strokes” bully The Gooch and suggesting that his competition find out what brown can do for him, Biggie delivered a verse that was both menacing and hilarious on the hottest hip-hop record of 1994.
3. “Hypnotize” (from Life After Death, 1997)
If you are at a party/wedding/social gathering, this song comes on, and people don’t completely lose their fucking minds, guess what? You are at the wrong party.
4. “Kick In The Door” (from Life After Death)
5. “I Got A Story To Tell” (from Life After Death)
It’s probably not a true story (no matter what attention whore Fat Joe might say), but BIG’s recollection of robbing a New York Knicks player after almost being caught mid-coitus with said baller’s girlfriend is conceptual genius along the lines of Slick Rick’s “The Moment I Feared”.
6. “Notorious Thugs” (from Life After Death)***
In which B.I.G. adopts Bone Thugs’ triple-time flow and out-rhymes all the Bone brothers combined. Another song that made me lose my shit when I first heard it.
7. “Gimme The Loot” (from Ready To Die, 1994)
Speaking of conceptual genius, here’s another song clearly influenced by Slick Rick. B.I.G. plays a tag-team of Brooklyn jackers. It’s a one-man Broadway show with a much funkier beat, oh…and robbery and murder.
8. “Juicy” (from Ready To Die)
9. “Brooklyn’s Finest” (from Reasonable Doubt, 1996)****
Giving his Brooklyn brother an assist on his classic debut album, Biggie delivered his most direct reference to the whole ‘Pac beef, giving credence to rumors about his wife, Faith Evans, consorting with ‘Pac by deadpanning “if Fay has twins, she’ll probably have two ‘Pacs/Get it? Tu…pac’s?” The clear chemistry that BIG and Jay share (present on all their records together) is completely forgotten in favor of this couplet.
10. “Warning” (from Ready To Die)
11. “Unbelievable” (from Ready To Die)
12. “Party & Bullshit” (from the Who’s The Man soundtrack, 1993)
Released before “Notorious” became part of his name, Biggie made his debut on the soundtrack to a forgettable film starring Doctor Dre (not the Compton MC/producer) and Ed Lover. A distinctly higher-pitched BIG steals the soundtrack with this gem. His conceptual genius is apparent even then-as the words “and a motherfuckin’ fight broke out!” are followed by what sounds like an actual fight. Dude had something special from the jump.
13. “Come On Motherfucker” (from Born Again, 1999)*****
Sadat X (of Brand Nubian) is, in my estimation, one of the five most underrated rappers of all time. “Come On Motherfucker” lived in the underground for half a decade before surfacing on Biggie’s first posthumous record. To steal a move from Robert Christgau, here’s the song’s inspirational verse: “you couldn’t touch my riches/even if you had MC Hammer and those .357 bitches.”
14. “One More Chance/Stay With Me” (single, 1995)
15. “Can I Get Witcha” (from Born Again)
16. “Victory” (from No Way Out)******
Featuring more unhinged Busta Rhymes.
17. “Get Money (remix)” (single, 1996)*******
18. “It’s All About The Benjamins (remix)” (from No Way Out) ********
One of the hottest hip-hop beats of all time, a fantastic song-closing Biggie verse, and this song is number eighteen. Still need to be convinced about what a beast the man was?
19. “Just Playing (Dreams)” (from Ready To Die-The Remaster)
The ’90s was a time when it became okay to appreciate (to put it nicely) men who were not stereotypically good-looking as sex symbols (see also: Shabba Ranks.) The songs at #14 and #21 are testament to Biggie’s smooth, conversational way with the come-on, but “Just Playing (Dreams)” (left off Ready To Die initially after lawsuit threats surfaced) is…uh, less smooth and more explicit. B.I.G. details fantasies about damn near every female R&B singer or group in existence during the mid ’90s. His lines would sound leering and kinda creepy if spouted by any other rapper (or singer), but B.I.G.’s clear sense of humor (even without actually titling the song “Just Playing”) makes the track palatable, even if his diss of Xscape is a bit of the ugly pot calling the ugly kettle black.
20. “Suicidal Thoughts” (from Ready To Die)
20+ years later and this song still gives me the chills. Less “horrorcore” and more “holy shit”, the closing track on Ready To Die hipped you to the part of the dealer/thug lifestyle that rappers have completely forgotten about in the last decade and a half.
21. “Big Poppa” (from Ready To Die)
22. “Ten Crack Commandments” (from Life After Death)
I can’t imagine Chuck D was too thrilled about hearing his voice on a song about drug dealing…but, hey.
23. “Player’s Anthem” (from Conspiracy, 1995) *******
24. “Mo Money Mo Problems” (from Life After Death)*********
A song like “Mo Money Mo Problems” would’ve been straight cornball in the hands of any other rapper, particularly at a time when much of the hip-hop community was still blatantly anti-commercial. However, hearing Biggie spit celebratory rhymes over a blatant jack of Diana Ross’s gay anthem “I’m Coming Out” somehow seemed right.
25. “Me & My Bitch” (from Ready To Die)
Language aside, this is a love song as much as it is a rap song. Soft-hearted but not corny, “Me & My Bitch” set the template for Method Man’s “I’ll Be There For You/You’re All I Need To Get By” (which actually used a sample from “M&MB”) and The Lost Boyz’ “Renee”.

*-of course, this is also subjective. But I’ll argue with anyone about this.
**- Craig Mack featuring The Notorious B.I.G., Rampage, LL Cool J & Busta Rhymes
***-The Notorious B.I.G. featuring Bone Thugs ‘N Harmony
****- Jay-Z featuring The Notorious B.I.G.
*****-The Notorious B.I.G. featuring Sadat X
******-Puff Daddy featuring Busta Rhymes
*******-Junior M.A.F.I.A. featuring Lil’ Cease, Lil’ Kim & The Notorious B.I.G.
********-Puff Daddy featuring The LOX, Lil’ Kim & The Notorious B.I.G.
*********-The Notorious B.I.G. featuring Puff Daddy & Ma$e

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