The 50 Best Notorious B.I.G. Songs

May 21, 2022 would have been The Notorious B.I.G.'s 50th birthday. Celebrating the legendary rapper's legacy, we're counting down Biggie's 50 best songs.

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This feature was originally published on July 22, 2017.

If you talk to any critic, new artist, hip hop head (young or old), or even the casual music fan, you’d be hard-pressed to find someone who wouldn’t cite Biggie Smalls as among the upper echelon of music legends. It’s difficult to believe that despite his early passing and with not having left behind the sprawling discography of other greats, The Notorious B.I.G.’s influence has lasted the test of time.

Born Christopher Wallace, the young rapper achieved what current artists and musicians strive to accomplish within a lifetime in just a short 24 years. His come-up occurred at a time when getting discovered as an artist took place in a strictly offline world. There was no Twitter to track and assess his every move, no SoundCloud for him to freely upload material for others to discover, and no blogs to promote—or denounce—his easy going flow and master storytelling. Biggie made a name for himself by relying on his talent, street savviness and charisma. 

Coming out hot with his debut Ready to Die in 1997, Biggie had the hip hop community’s attention. His easy-going flow, smooth persona, and instantly recognizable voice quickly captured listeners admiration.

Capitalizing on the burgeoning East Coast rap scene, B.I.G. finessed his way to the top of the charts and became a household name. A gifted MC, comedic storyteller, and revolutionary rap artist, he transcended his too-familiar upbringing and rose to claim his rightful title as King of New York.

Artists today might dream of having the success and lasting impact that Biggie has achieved, but that magic is reserved for only a special few. As time goes on, one thing is certain: Biggie will always be one of the greatest to ever do it.

May 21, 2022 would have been Biggie’s 50th birthday, and the rap world is remembering the legacy of the late New York legend. Today, we’re counting down his 50 best songs.

50. 2Pac f/ The Notorious B.I.G., Stretch, & Dramacydal "Runnin' From Tha Police" (1995) / 2Pac f/ The Notorious B.

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Producer: Easy Mo Bee / Eminem

Album: One Million Strong / Tupac: Resurrection OST

Label: Amaru / Amaru

Originally recorded for 2Pac's Thug Life side-project, “Runnin' From Tha Police” was cut by Interscope due to heavy criticism of gangsta rap and anti-law enforcement sentiment at the time. The track was to find a second life on Pac's Me Against The World album a year later, but after his 1994 shooting, Pac's relationship with Biggie Smalls changed drastically.

2Pac and the Notorious B.I.G.'s only real studio collaboration would later land on the obscure One Million Strong compilation, and largely fly under the radar, despite the well-publicized beef between the two rappers.

In 2003, the track was resuscitated one more time, when Biggie and Pac's verses were spliced together with interviews over a shiny new Eminem beat for “Runnin (Dying To Live).” Eminem's remake was a good way to stir up interest for Pac's Resurrection documentary, cracking the Top 20 on Billboard, pushing the soundtrack to Platinum. Nine years later it still stirs up feelings of loss.

49. The Notorious B.I.G. "Things Done Changed" (1993)

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Producer: Fabian Hamilton

Album: Ready To Die

Label: Bad Boy

Inner city life was completely transformed in the early '90s. Parents could no longer control their children as feelings of hopelessness and desperation ran rampant. Instead of solving their problems with fists, many kids were now armed and dangerous. The OGs could no longer control the BGs, and with the influx of crack, shit got real.

Big summed it up best with his unforgettable slogan: “The streets is a short stop/Either you're slanging crack rock or you've got a wicked jump shot.” More than just narrating the societal shift, Biggie gave listeners a first-hand account of urban life as he saw it—right down to his personal tragedies like his mother's real-life breast-cancer diagnosis.

48. The Notorious B.I.G. f/ Kelly Price "Nasty Boy" (1997)

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Producer: Steven "Stevie J" Jordan, Sean "Puffy" Combs

Album: Life After Death

Label: Bad Boy

Likely inspired by West Coast potty mouth Too $hort; Biggie Smalls hosted a collection of “Freaky Tales” of his own on “Nasty Boy.” Recounting various sexcapades, Big kissed and told in the nastiest way possible.

Whether it be the half-Indian lover he called Tonto, or freaks down for the one night stand, Big was getting it in on the female tip—and was arrogantly unapologetic about it. While it's always debatable whether or not you liked the song, there's no denying you got a hearty chuckle when you first heard the feces-related opening skit. That's that shit.

47. Funkmaster Flex "The Notorious B.I.G. & The LOX Freestyle" (1997)

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Producer: N/A

Album: The Mix Tape Vol. II

Label: Loud

This three-minute freestyle, tacked on to a lengthy Funk Flex mixtape, was the world's introduction to Bad Boy's newest edition—the three kids Living Off Xperience from Yonkers. These young and hungry MCs were eager to show and prove on the mic, verbally competing for the champion verse.

Obviously the elder statesman, Biggie Smalls, had a reputation to uphold, and couldn't be outdone by the new kids on the d-block. Big made sure his verse was chock-full of quotables, claiming his “gun burn, much hotter than sunburn” and professing he “got stripes in New York like Yankee uniforms.” But Big swagged all the way out with the whole “No frills cereal with food stamps/To Armani material, copping Rembrandts” stunt.

Everyone put their best foot forward, and while the Lox would later be cleaned up and repackaged as a jiggy band, their world premiere was straight black hoodie rap.

46. The Notorious B.I.G. f/ Method Man "The What" (1994)

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Producer: Easy Mo Bee

Album: Ready To Die

Label: Bad Boy

In 1994, Method Man was arguably the most popular new hip-hop artist on the planet. His natural charisma and witty, unpredictable talent set Meth apart from his Wu brethren, so it was only right that Biggie enlisted his services for “The What.” Nothing short of epic, the track featured two budding MCs trading calculated battle bars back and forth while cleverly finishing the last words of each others' verses.

“The What” turned out cold as the Pole in the winter, with both rappers spewing quality lines that were accepted by kids with chewsticks and bottle-poppers alike—they even tapped into that hard-to-reach female audience. The track also sparked an eternal debate: Who murdered who?

45. Crustified Dibbs f/ The Notorious B.I.G. "Cunt Renaissance"

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Producer: Marc Nilez

Album: Legendary Classics Vol. 1

Label: Nature Sounds

Meeting through the Trackmasters' Tone, the artist known as R.A. The Rugged Man and Biggie Smalls are responsible for quite possibly the most offensive rap song ever. Known to the industry as an uncontrollable troublemaker, Rugged Man.

When R.A.'s label caught wind that the Rugged Man was going in the studio with Biggie Smalls, they asked him to churn out something along the lines of “Juicy,” so they could market to radio, piggybacking off the success of Ready To Die. But the Rugged Man did just the opposite. With other plans in mind, the devious MC would go on to craft one of hip-hop's most vulgar and unrefined hip-hop records of all time, “Cunt Renaissance.”

The title itself was cringe-inducing, featuring that most taboo of curse words: the dreaded C-word. R.A. allegedly recorded his verses first, and not to be outdone by Crustified, Big went in and laced arguably the nastiest verse of his career—anal, oral and fisting were all name checked here. The result was dope if also disgusting. And while Crustified never matched the solo success of Big, he was able to bring out of the King of New York's nasty side.

44. The Notorious B.I.G. f/ 112 "Miss You" (1997)

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Producer: Kay Gee

Album: Life After Death

Label: Bad Boy

No stranger to tragedy, “Miss U” found Big telling three stories about various acquaintances who, one way or another, had fallen victim to the struggle. Whether by stray shots or getting knocked, Big could relate.

Playing the part of a heavy-hearted street cat, Big made a record about love and loss that everyone could relate to—even if their “struggle” was different. The pairing of Kay Gee's organs and harps with 112's light vocals provided a somber yet melodic way to reminisce. The track was all the more bittersweet because soon after he recorded it we were missing Big as well.

43. The Notorious B.I.G. "Ready To Die" (1993)

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Producer: Easy Mo Bee

Album: Ready To Die

Label: Bad Boy

Biggie's obsession with death is littered throughout his entire catalog. Hell, both his album titles directly referenced it. But on Ready To Die's title track, Chris Wallace really went there, desperately claiming “I'm ready to die and nobody can save me.”

Big may have felt his “Life is played out like a jheri curl” by the time he'd reached his early 20’s, but despite the tracks dark tone, he still found time to inject the comedic “I got techniques drippin' out my buttcheeks/Sleep on my stomach so I don't fuck up my sheets.”

42. Busta Rhymes f/ The Notorious B.I.G. & Labba "Modern Day Gangstas" (1996)

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Producer: J Dilla

Album: N/A

Label: N/A

The details are sketchy and vary depending on what you read or who you're talking to, but “Modern Day Gangstas” was allegedly slated for a Busta Rhymes project. The track, produced by another fallen hip-hop icon, J Dilla, featured Biggie Smalls and Labba. Prior to Dilla's death, the producer claimed Nas was also to appear, but when the song was scrapped, the feature was as well.

Recorded at the height of the Biggie vs. 2Pac feud, Big's verse was littered with not-so-subliminal shots at Makaveli. And while many brushed off “Who Shot Ya” and “Long Kiss Goodnight” as pure coincidence, there was no mistaking who Big Poppa was popping at here: “And the winner is, not that thinner kid/Bandanas, tattoos, my fists never bruise.”

Big went on to call Pac an actor, claiming to have rocked his chatter box, and that despite all the tough talk he wasn't “dangerous.” Any further suspicions were alleviated with: “By now you figure, he talkin' bout that nigga/But your weak-ass assumptions, lead lead to dumpin.”

Finding himself caught in the middle, Busta canned the track, crushing rap fans' dreams of hearing Biggie over a Dilla beat—until it was liberated on mixtapes some years later. Big's verse would also find a home on Born Again, remixed and repurposed as “Dangerous MCs.”

41. The Notorious B.I.G. "Me & My Bitch" (1993)

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Producer: The Bluez Brothers, Chucky Thompson, Sean "Puffy" Combs

Album: Ready To Die

Label: Bad Boy

Sure, Big played the part of the ultimate ladies man—but don't let the playa persona fool you. He cherished his ride or die girls. On “Me & My Bitch,” Poppa gave it up for the one he wanted to spend eternity with. But as the song makes clear, love doesn't come without a price.

There's a thin line between love and hate, and Big's main squeeze wasn't to be tested. Threatening to cut off his manhood—even toss his Polo's and Timbo's out the window—for adulterous activities, his lady ran a tight ship. But on the flip-side this down-ass chick shot dice and helped B.I.G orchestrate his robberies.

Their love story came to a tragic end on the day she hit him with 911 on the pager (now only an ancient relic, 911 was a used-and-abused emergency code for pagers). Attempting revenge on Big (presumably for one of the heists?) goons ran up in his crib and murked his lady instead.

40. The Notorious B.I.G. f/ Roger Troutman "Going Back To Cali" (1997)

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Producer: Easy Mo Bee

Album: Life After Death

Label: Bad Boy

As proven on "Notorious Thugs," Big was a beast at replicating regional rap. Despite his much-advertised beef with certain factions on the Left Coast, Biggie had much California love, as he professed on "Going Back To Cali." Just because he was embattled in a feud with Pac & Suge, didn't mean he'd stop giving L.A. props.

Over slapping West Coast synths that sounded more Battlecat than Easy Mo Bee, Big gave it up for the state from which he had been unfairly blackballed, running down a laundry list of reasons why he loved Cali.

It was a bold and fatal move for Big to be high-posting in L.A., but he just couldn't resist the weather, the women, and the weed. This record demonstrated that the East Coast vs. West Coast beef was mostly a media creation—less a the battle of two coasts than a beef between two factions. However, the ultimate irony was that when Biggie was fatally shot on March 9th, 1997, "Going Back To Cali" was the song that he was bumping in the whip.

39. Sadat X f/ The The Notorious B.I.G. "Come On"

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Producer: Lord Finesse, DJ Clark Kent

Album: Born Again

Label: Bad Boy

Many refused to believe that a commercial superstar like Big would get down with an underground king like Sadat X— but Biggie was a b-boy at heart who loved hardcore underground rap. In fact, that's all he wanted to record for Ready To Die, but it didn't quite work out that way.

There has always been a bone of contention surrounding Big and Sadat's “Come On.” The track was allegedly recorded for Big's Ready To Die album, but was scrapped by Puff at the last minute for not fitting the format of the magnum opus.

Perhaps Sadat wasn't quite popping enough? Or was it that he was "kind of spiritual"? Maybe the track itself just wasn't up to par? For whatever reason, this Lord Finesse–produced knocker was left on the cutting-room floor. Years after Biggie's death, “Come On” would appear on the posthumous Born Again album, but with a new beat provided by Clark Kent. And while it was great to see the record get an official release, the Lord Finesse original was far superior.

38. The Notorious B.I.G. "Somebody's Gotta Die" (1997)

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Producer: Nashiem Myrick, Carlos "6 July" Broady, Sean "Puffy" Combs

Album: Life After Death

Label: Bad Boy

"Somebody's Gotta Die" was an eerie way to kick off Big's second album. His words were so cinematic, even those with the weakest imaginations could watch the action play out in their minds. While Big was lauded for his use of punchlines and double-entendres, he was also an excellent storyteller. Many rap songs are pathetically predictable, but "Somebody" was a whole different caliber. A rap song vivid enough to turn your stomach? Yeah, Big did that.

From Sing showing up at Big's door at 3:52am with bloody sneakers, clutching a chrome .45, to plotting the retaliation of his fallen comrade C-Roc behind Diddy's back ("Puff won't even know what happened") the tale was all too real. And that final moment, when Big's adversary Jason turned around holding his daughter, amidst the sound of gunshots, raindrops and a crying baby? Street cinema at its finest.

37. The Notorious B.I.G. "Real N****s" Freestyle (1995)

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Producer: N/A

Album: N/A

Label: N/A

While Biggie and Bad Boy shaped the sound of the East Coast, supplying the yin to Death Row and the West Coast's yang, it was no secret Big had nothing but love for the Left Coast g-funk sound. He evidenced this on the promo cassette “Real Niggas,” in which he freestyled over such Cali gems as “G Thang,” “Black Superman” and “Murder Was The Case.”

Kicking his patented humble-brags, Big proclaimed he'd bought wifey a house and Junior Mafia an arcade. He even found time to shout out Death Row at the end—officially the last time we'd ever hear that. And if the final verse (over “Gin & Juice”) sounds familiar, it's because it was later used for Biggie's posthumous single “Notorious” featuring Lil Kim and Diddy. Jay-Z would also borrow the hook for a song of the same name.

36. The Notorious B.I.G. "Suicidal Thoughts" (1994)

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Producer: Lord Finesse

Album: Ready To Die

Label: Bad Boy

Ready To Die gave us a first-class trip into the mind of Christopher Wallace. We saw all facets—some bright, most dark. Two recurring themes on his debut were depression and desperation, both inflamed by street life during New York's early '90s crack boom.

“Suicidal Thoughts” found Big conflicted about the life he was living, expressing such troubling thoughts as: “I know my mother wish she got a fucking abortion,” and saying he preferred to spend eternity in hell than with the so-called "goodie goodies" who ostracized him on earth.

While his will was weak, he hit Puff one last time to get his final thoughts off his chest: “I'm sick of niggas lyin', I'm sick of bitches hawkin'/Matter fact, I'm sick of talkin'.” The song ends with a single gunshot followed by the sound of a heart stopping and a phone left off the hook. Chills.

35. Puff Daddy f/ The Notorious B.I.G. & Jay-Z "Young Gs" (1997)

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Producer: Rashad Smith

Album: No Way Out

Label: Bad Boy

Big always held his own when rhyming alongside his peers, but it was Jay Hova who brought the best out of him. On their third and final collab, which found a home on Diddy's No Way Out, the two legendary MCs traded intricate mafioso drug tales that had us forgetting that Puff was on verse one.

“Young G's” was the only record on No Way Out not produced by one of Bad Boy's Hitmen, with Rashad Smith supplying the smooth, playalistic backing. Per usual, Big's verse was larger than life, with talk of murda mami's with bullet proof vests under their coochie, and driving dirty in J30's. Big's lyrical carjack, even gave listeners the helpful tip of hiring lawyers to watch lawyers so you won't go broke. Duly noted.

Accurately foreshadowing the future, Jay promised Big he'd be (multi) platinum before he died. He made good on that promise just a year later. Damn it feels good to see people up on it.

34. The Notorious B.I.G. "I Got A Story To Tell" (1997)

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Producer: Buckwild, Chucky Thompson, Sean "Puffy" Combs

Album: Life After Death

Label: Bad Boy

Anyone even remotely familiar with Frank White's catalog knows he was an impeccable storyteller. And with a title like "I Got A Story To Tell," this song has to be a gem. Rumored to have been based on a real-life episode involving former NBA guard John Starks, “Story To Tell,” found Big holed up with a scandalous honey “who got dick from a player off the New York Knicks.”

When the ball player in question shows up during the rendezvous, Big comes up with a plot twist that's sicker than anything M. Night Shyamalan—or even R. Kelly—ever imagined. Flipping the tables on the player, he quickly turns his love-making session into a full-blown 211. Hilarity ensues, leading B.I. to hit one of the biggest licks of his life. This story was a classic.

33. The Notorious B.I.G. "What's Beef?" (1997)

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Producer: Nashiem Merick, Carlos "6 July" Broady, Paragon

Album: Life After Death

Label: Bad Boy

While Big's time in the spotlight was short, his laundry list of adversaries was long. After all the shots sent his way by the likes of Pac and Death Row, fans anticipated a response from Biggie on Life After Death. After ripping the plastic of the album, many listeners went straight to track eight on disc one to see what beef was all about.

But to let Big tell it, rap beef wasn't real beef. Nah, beef was something else entirely. Biggie had heat and tough talk for his foes, and threatened to kidnap and torture anyone who crossed his path.

He even got pause-worthy by mentioning that his goon, Gutta, liked to sodomize dudes and toss them over bridges. Big didn't call anyone out by name, but "Beef" was a reminder that just because he was quiet, didn't mean he wasn't ready for war.

32. The Notorious B.I.G. f/ R. Kelly "Fuck You Tonight" (1997)

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Producer: Daron Jones, Sean "Puffy" Combs

Album: Life After Death

Label: Bad Boy

Before Robert Kelly and Shawn Carter showed us the Best of Both Worlds, Big was laying his pimp hand down alongside the Windy City crooner. It may have sounded like a love song, but it was just the complete opposite.

Is it tricking if you got it? We're still not sure, but Big and the R were skipping dinner, drinks and shopping and heading straight to your mother's bed. Spending? Wining and dining? Nah love, that's not on the agenda tonight. No love making, strictly back-breaking. And Big was such a G, he made his loyal hypeman Lil Cease settle for sloppy seconds.

31. The Notorious B.I.G. f/ 112 "Sky's The Limit" (1997)

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Producer: DJ Clark Kent

Album: Life After Death

Label: Bad Boy

Life After Death had its darker moments, but it also featured some of Big's most vibrant and inspirational work. "Sky's The Limit" was a reminder that no matter what circumstances you were born into, you could rise above to find success (be it legal or illegal). Big once called it the best song he ever made.

With a smooth hook courtesy of 112, the song was an ashy-to-classy tale of a boy who once sewed tigers and alligators on his shirts, and went on to become the neighborhood boss whose orange box cutter made the world go 'round.

After Frank the Deputy shared his stories of master enterprising, he blessed us with a hustlers prayer to live by, consisting of five key elements: 1.) put money in your Moms hand 2.) get your kids a college plan 3.) stay far from timid 4.) only make moves when your hearts in it 5.) live the phrase sky's the limit.

30. Puff Daddy f/ The Notorious B.I.G. & Busta Rhymes "Victory"

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Producer: Sean "Puffy" Combs & Steven "Stevie J" Jordan for The Hitmen

Album: No Way Out

Label: Bad Boy

This one is NYC Mafioso rap at its finest. Sure, it was Diddy's track, but the murderous, most shady, Frankie Baby owned it. Biggie let it be known it was a family affair by shouting out all the Bad Boys: “Break bread with the Kiss, Pinero, Sheek Louch/Black Rob joined the mob, it ain't no replacing him/Niggas step up, we just macin' (Ma$e'n) them.”

But it was Biggie's “I perform like Mike/Anyone: Tyson, Jordan, Jackson” routine that stole the show, and will undoubtedly go down as one of the greatest hip-hop lines of all time. Ask Cam'Ron, Jay-Z, and the countless other MCs who've paid homage to it.

The last verse Biggie ever recorded was flawless, and still sounded victorious even though it dropped five months after his untimely passing.

29. The Notorious B.I.G. "Long Kiss Goodnight" (1997)

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Producer: RZA

Album: Life After Death

Label: Bad Boy

Speculated to be filled with subliminal shots aimed at 2Pac and Suge Knight, “Long Kiss” is a dark and haunting soundscape that anchored the bottom half of Life After Death. At the time of its release, the world was still reeling from the deaths of both artists, so the diss was very much downplayed. Puffy steadfastly denied that the track was aimed at Death Row, but Lil Cease has maintained that it was a bottle of ether for Pac.

While it's true that Biggie could've just been firing off at sucker MCs, some lyrics hit a little too close to home to be mere strokes of coincidence. Zingers like “Heard through the grapevine, you got fucked four times,” call to mind rumors that Pac was stripped of his manhood in prison—not to mention the whole “Slugs hit your chest, tap your spine, flatline” sequence. Yes, it would've been in poor taste to have admitted that this record was aimed at Pac in '97. But now, the evidence seems overwhelming.

28. The Notorious B.I.G. f/ Puff Daddy, Ma$e & Kelly Price "Mo Money Mo Problems" (1997)

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Producer: Steven "Stevie J" Jordan, Sean "Puffy" Combs

Album: Life After Death

Label: Bad Boy 

1997 was the year the jiggy sound first popped off. Popularized by Puff and his Hitmen production squad, the sound drew heavily from hit records of the '70s and '80s. dressed them up with hip-hop drums (and those infamous bells), and flipped them into full-fledged rap tunes.

The era didn't come without its fair share of criticism, though. As the jiggy poster boy, Puff Daddy caught much flack for his blatant jacking of already proven hits. Production snobs cried foul when Diddy simply reused known loops. There was no skill in this – or so they thought.

No song exemplifies the jiggy era better than “Mo Money, Mo Problems.” And despite sniping by hip-hop purists, the record never failed to bring people to their feet and get club patrons spilling their drinks all over the dance floor.

“Mo Money” was also noteworthy for showing the transition from Puff the exec to Puff the rapper as well as serving to introduce Bad Boy's new kid on the block, Mason Betha, whose golden-boy charm quickly won over fans.

Big's closing verse was the icing on the cake as B-I-G/P-O/P-P-A effortlessly flexed over the track, kicking some of the most focused bars of his career. Fifteen years later, the man with no info for the DEA, still has people throwing their Rollies in the sky.

27. The Notorious B.I.G. "Niggas Bleed" (1997)

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Producer: Nashiem Myrick, Carlos "6 July" Broady, Steven "Stevie J" Jorda

Album: Life After Death

Label: Bad Boy

Another immaculate storytelling saga from Chris Wallace, "Niggas Bleed" boasts perhaps the most memorable opening line ever: “Today's agenda, got the suitcase up in the Sentra.” Street narratives were Biggie's bread and butter, as he could evoke the essence of people, places, and things using details that were not only vivid but also hilariously random.

Describing a dread-headed security guard as Maxi Priest, clicking up with his awesomely named homie, Arizona Ron from Tucson (who was rumored to be based on 2Pac), and being wary of dudes in showers with mac-millis, “Niggas Bleed” was another motion picture put to audio. Complete with a hilarious twist at the end. That's why they call him the Alfred Hitchcock of rap.

26. Biggie Smalls "The Wickedest" (Mr. Cee) (1994)

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Producer: N/A

Album: The Mix Tape, Vol. 4: 60 Minutes of Funk

Label: Loud

The legendary DJ Mr. Cee is largely responsible for Big's big break. He created the demo that lead B.I.G. to The Source's coveted "Unsigned Hype" column and later into the hands of then-budding executive Sean Combs.

Recorded by Cee in 1994, Biggie effortlessly crushed Casual's “I Didn't Mean To” instrumental, kicking his standard eyebrow-raising lyrics: “Biggie Smalls is the Wickedest/Niggas say I'm pussy, I dare you to stick your dick in this/If I was pussy I'd be filled with Syphilis/Herpes, Gonorrhea, Chlamydia/Gettin' rid of ya.”

The freestyle would later find a home on Funkmaster Flex's The Mix Tape, Vol. 4: 60 Minutes of Funk, which was released in 2000—a true treasure for those unfamiliar with Cee's early mixtapes.

25. Puff Daddy f/ The Notorious B.I.G., Lil Kim & The LOX "It's All About The Benjamins" (1997)

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Producer: Deric "D. Dot" Angelettie

Album: No Way Out

Label: Bad Boy

“Benjamins” was once (and tbh, still is) the quintessential club banger. From the beat, to the hook, to the bridge, it's a flawless party starter and couch-dancing anthem.

Capping off this incredible remix (the original featured only the Lox and Puff), was Francis the praying mantis, who effectively tore the track to shreds, becoming the only MC to rhyme over a different beat.

24. The Notorious B.I.G. "Just Playing (Dreams)" (1993)

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Producer: Rashad Smith

Album: Ready To Die

Label: Bad Boy

Before B.I.G. blew with “Juicy,” he could only dream of boning the hottest R&B honeys in the game. And Faith wasn't even on the radar yet. On this hilariously vulgar B-side, Biggie waxed poetic about his favorites. As usual Big pulled no punches, questionably name-dropping Raven Symone (she was what, nine at the time?), and turning his nose up at “them ugly ass Xscape bitches.” Ouch. Everyone from Mary to Whitney to Ru Paul got it. This concept was used and abused by countless other rappers—male and female alike. Controversy sells, and none knew this better than Big.

23. Total f/ The Notorious B.I.G. "Can't You See?" (1995)

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Producer: Sean "Puffy" Combs, Rashad Smith

Album: New Jersey Drive, Vol. 1 OST

Label: Tommy Boy/Bad Boy

After Total laced “Juicy” and “One More Chance” with their luscious background vocals, Big returned the favor on the trio's 1995 debut single “Can't You See.” Leading off the track, Big dominated the intro, asking for all the chicken heads from Pasadena to Medina, and making more explosion references than you could shake a stick at. His rap lines truly were like landmines.

Living Total's mantra "Beside every Bad Boy, there is a Bad Girl," Big helped propel the single to Gold status. Big was a team player, and proved a simple sixteen from him was enough to draw interest and help push the New Jersey Drive Soundtrack and Total's debut album to RIAA certification as well. Bad Boy slipped in 95? Ridiculous.

22. The Notorious B.I.G. "Party and Bullshit"

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Producer: Easy Mo Bee

Album: Who's The Man soundtrack

Label: Uptown

A terror since the public school era, Big and his Brooklyn boys knew how to turn out a party. So it was no surprise that the first single of his career was entitled “Party and Bullshit.” A year before “Juicy” kicked off Ready To Die, the fourth single released from the Who's The Man? Soundtrack introduced Biggie to the world. (The track was a favorite of 2Pac's before he and Big became rivals.)

While “Party and Bullshit” was the polar opposite of Big's later party anthems, it showcased how a young, unrefined Big got down. Before chilling with Puff in bathtubs filled with Cristal, Big's parties consisted of bullet-proof vests, Heinekens, and plenty of blunts in rotation.

21. The Notorious B.I.G. f/ Bone-Thugs-N-Harmony "Notorious Thugs" (1997)

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Producer: Steven "Stevie J" Jordan, Sean "Puffy" Combs

Album: Life After Death

Label: Bad Boy

To kick off disc two of his Life After Death masterpiece, Big took it to the crossroads of America for some Midwest bounce. "Notorious Thugs" stands as a testament to just how popular Bone Thugs-N-Harmony were in that era, as they were the only group to have worked with Biggie, Pac, Pun, and Eazy-E before those rappers' untimely deaths.

High off weed and lots of gin, Big out-rapped and out-harmonized Cleveland's Bone Thugs, taking their double-time flow and upping the ante. Seamlessly integrating himself into the track, Chris Wallace sounded like the sixth member of the Ruthless collective. Big's words were clearer, crisper, and easier to understand than those of his Mo Thug counterparts—and exhibited amazing breath control for such a big boy (pun intended).

Big even nonchalantly—albeit briefly—addressed his so-called beef with you-know-who, which proved rather unsettling because by the time we heard the track, both artists were gone. After "Notorious Thugs," countless other rappers would try their hand at their sound, but none did it quite like B.I.G.

20. 112 f/ Ma$e & The Notorious B.I.G. "Only You" (1996)

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Producer: Steven "Stevie J" Jordan, Sean "Puffy" Combs

Album: 112

Label: Bad Boy

Jesus, the Notorious pleased us with his lyrical thesis on 112's remix to their hit “Only You.” Putting a hip-hop spin on traditional R&B, Puff and Bad Boy had Big lead off the track while a fresh-faced Mase closed it out. The Escada Don Dada mentioned the usual luxury brands and shouted out Cease, but when he name-dropped his accountant, Bert Padell, many listeners were left scratching their heads. Pre-Google, people outside of NYC had no idea who the hell Big was talking about.

19. The Notorious B.I.G. f/ 2pac "Live Freestyle" (1993)

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Producer: N/A

Album: The Tunnel

Label: Def Jam

During a 1993 Big Daddy Kane concert at Madison Square Garden, the smooth operator invited Biggie Smalls and Tupac Shakur onstage to freestyle for the packed arena. Thinking he was recording a run of the mill cipher, Kane's DJ Mr. Cee, who was in the habit of recording every show, had no idea he was about to capture a piece of history. After this performance, nobody would have to wonder "Where Brooklyn at?" ever again.

At the time, Big and Pac were chums—running in the same circles, partying and bullshitting throughout New York City. Big hit the stage like a cannon, kicking off his firearm-inspired verse with the classic “I got seven Mack-11's, about eight 38's, nine 9's, 10 Mack-10's...” He went on to take hilarious shots at MC Hammer and Oaktown's 357. Pac's verse wasn't quite as “lyrical,” but the energy and sincerity he displayed in his words were chill-inducing.

Shyheim and BDK-baggage-handler Scoob, also participated in this historical moment, but their contributions have been largely swept under the rug. While the other MCs deserve their just due, the camaraderie on display between Big and Pac outshines everything else on the stage, raising poignant questions of what might have been.

18. Junior M.A.F.I.A. "Get Money" (1995) / Junior M.A.F.I.A f/ The Notorious B.I.G. "Gettin' Money (The Get Money

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Producer: DJ Enuff, Lance "Un" Rivera, The Notorious B.I.G.

Album: N/A

Label: Big Beat

Biggie Smalls was one of the illest to ever do it. Period. But the world had no choice but to respect Jay-Z as a major contender for the NY throne after hearing him go toe-to-toe with Frank White. It's clear both MCs were quietly battling each other, but this competitive spirit brought out the best in both. Loaded with quotables, “Brooklyn's Finest” found Biggie taking playful jabs at his wife Faith Evans and the bogus rumors about her affair with 2Pac: “If Faye had twins she'd probably have two Pac's. Get it? Two. Pacs.”

This would be the first of just three collaborations the two would record prior to Big's demise. Would The Commission have come to fruition? Would these two have kept the spirit of friendly competition alive? Those questions, and more, will haunt us forever.

17. Jay-Z f/ The Notorious B.I.G. "Brooklyn's Finest" (1996)

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Producer: DJ Clark Kent

Album: Reasonable Doubt

Label: Roc-A-Fella/Priority

Biggie Smalls was one of the illest to ever do it. Period. But the world had no choice but to respect Jay-Z as a major contender for the NY throne after hearing him go toe-to-toe with Frank White. It's clear both MCs were quietly battling each other, but this competitive spirit brought out the best in both. Loaded with quotables, “Brooklyn's Finest” found Biggie taking playful jabs at his wife Faith Evans and the bogus rumors about her affair with 2Pac: “If Faye had twins she'd probably have two Pac's. Get it? Two. Pacs.”

This would be the first of just three collaborations the two would record prior to Big's demise. Would The Commission have come to fruition? Would these two have kept the spirit of friendly competition alive? Those questions, and more, will haunt us forever.

16. Mary J. Blige f/ Biggie Smalls "Real Love (Remix)" (1992)

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Producer: Mark C. Rooney, Mark Morales, Sean "Puffy" Combs, Daddy-O

Album: N/A

Label: Uptown

By the time Big passed in 1997, he was the poster boy for the hip-hop/R&B duet. Time and again, he proved the perfect recruit to eloquently thug out the softer sounds that were so popular on the radio. His verses worked like a charm—converting heads who otherwise wouldn't have been caught dead bumping slow jams. But back in '92, he was very much unproven.

Though it was only the rapper's second guest appearance, Puff believed in Big enough to add him to the remix of “Real Love,” the breakout song by Diddy's other muse, Mary J. Blige. Still rocking with the Biggie Smalls moniker (before switching to Notorious thanks to an obscure white rapper who'd already trademarked the name), the unapologetically grimy Biggie stole the show with his “Look up in the sky it's a bird it's a plane” intro. Sure Big was rough around the edges, but he didn't sound at all out of place alongside Ms. Mary. On this day a star was born.

15. The Notorious B.I.G. "Everyday Struggle" (1993)

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Producer: Norman & Digga, The Bluez Brothers

Album: Ready To Die

Label: Bad Boy

Sure Biggie had glossy singles, but the meat and potatoes of the album was a grimy affair. Biggie was fresh off the block, and could still relate to the plight of the street-level hustler. He was yet to hit don status, so he dealt with the everyday struggle of the hand-to-hand supplier. But this wasn't a life Chris Wallace enjoyed living. "Sometimes," he rapped, "I hear death knocking at my front door."

“Everyday Struggle” tells the tale of a low-level drug dealer traveling the country attempting to make it in the criminal underworld. Sure the story was intriguing, but it was Big's dizzying wordplay and layered bars that made it classic: “I heard Tech got murdered, in a town I never heard of/By some bitch named Alberta, over nickel-plated burners.”

14. The Notorious B.I.G. f/ Faith Evans & Mary J. Blige "One More Chance" (1994)

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Producer: The Bluez Brothers, Chucky Thompson, Sean "Puffy" Combs

Album: Ready To Die

Label: Bad Boy

Although he may have been an unlikely candidate for hip-hop sex symbol, Big waddled further into that territory on the “One More Chance (Remix)." Not included on initial pressings of Ready To Die, the remix featured a brand new beat, lyrics and chorus—all more radio friendly than on the original.

Big took his Casanova role to the next level, professing he was "not only a client," but "the player president." Switching honeys like musical chairs, Big ushered them in and out with ease: “Isn't this great, your flight leaves at eight/Her flight lands at nine, my game just rewind.”

Released in the spring of '95, the remix was an instant smash, tying a record set by Michael Jackson and The Beatles for the highest debuting single when it entered Billboard's Hot 100 at No. 5.

13. The Notorious B.I.G. f/ Eminem "Dead Wrong (Remix)"

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Producer: Chucky Thompson & Mario Winans

Album: Born Again

Label: Bad Boy

While the majority of Big's posthumous material was was spotty at best, the brightest moment on the Born Again album was his “Dead Wrong (Remix),” featuring the red-hot-in-1999 Eminem. Biggie's vocal was lifted from a Mister Cee Best Of Biggie mixtape, and flawlessly remixed.

The original Easy Mo Bee beat was booted in favor of a more contemporary Al Green-sampling banger courtesy of the Hitmen. Big's voice, cadence and flow were clearly from his pre-superstar days, but with the help of Eminem's brilliantly off-color and ultra-violent verse, it sounded right in place with the sound of the late-'90s. Unfortunately the remainder of Born Again was a patched together mess—but it still went triple-platinum on the strength of this track and Biggie's name alone.

12. The Notorious B.I.G. "Gimme The Loot" (1993)

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Producer: Easy Mo Bee

Album: Ready To Die

Label: Bad Boy

Big plays two different characters on "Gimme The Loot": One, the cool and calm stick up kid, the other an overly aggressive jux puller with an itchy trigger finger. Both are on a mission for that ultimate lick—by any means. Crazier than a bag of angel dust, these two were sticking everyone: kids, high school students, pregnant mothers. The cops would later thwart the duo's plan, and while we don't know exactly how the tale ends, we have a feeling it was violent.

11. The Notorious B.I.G. "Machine Gun Funk" (1993)

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Producer: Easy Mo Bee

Album: Ready To Die

Label: Bad Boy

There may be no better way to describe the sound Easy Mo Bee gave Biggie on Ready To Die, than the title of the song. Together, Big and Mo Bee sold bags of machine-gun funk by the ton, seamlessly weaving traditional NYC boom-bap with funk-inspired bass lines and samples. This was Big at his grimiest: Kicking exceptionally rough and rugged bars, Frank White beat the track "like Ike beat Tina." Yeesh.

10. Junior M.A.F.I.A f/ The Notorious B.I.G. "Player's Anthem" (1995)

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Producer: DJ Clark Kent

Album: Conspiracy

Label: Big Beat

Chris Wallace repped for his Junior Mafia crew from day one—before we had any idea what it was or who was in it, Big was shouting out JM on records. Composed of childhood friends and associates from his BK stomping grounds, the 10-man collective inked a deal with Big Beat on the strength of Biggie's success (and industry connects).

Big always went above and beyond for his fellow Brooklynites, so it was no surprise to learn years later that Big wrote the entire song. Yep, those are Biggie's words being spewed by Kim and Cease. The Smalls, bitch, who you thought it was supposed to be?

9. The Notorious B.I.G. "Ten Crack Commandments" (1997)

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Producer: DJ Premier

Album: Life After Death

Label: Bad Boy

Biggie had been in this game for years, so it was only right for him to share some tricks of the trade. This song was a step-by-step manual of rules for dealers seeking a long-lasting and fruitful career in the crack game ("get your game on track, not your wig pushed back.").

Rules such as not mixing blood and money and never getting high on your own supply were beat into the heads of countless would-be students.

With such brazen subject matter, it's no surprise the song proved to be controversial. Shortly after the track dropped, Public Enemy's Chuck D, whose voice was sampled by DJ Premier for the countdown, sued for copyright infringement.

The parties settled out of court for a sizeable sum in 1998. Apparently Chuck didn't like his voice being associated with crack, as he'd always had a strong anti-drug stance (see “Night of the Living Baseheads”).

8. Craig Mack f/ The Notorious B.I.G., Rampage, LL Cool J & Busta Rhymes "Flava In Ya Ear (Remix)" (1996)

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Producer: Sean "Puffy" Combs, Chucky Thompson

Album: N/A

Label: Bad Boy

In the Fall of '94, Puff's BIG-MACK cross-promotion campaign for Bad Boy's two flagship artists, Craig Mack and The Notorious B.I.G., was hauling ass. Both artists' debut albums were released within a week of each other, each with bubbling first singles. But what Biggie did to the “Flava In Ya Ear (Remix)” was the nail in the coffin for Craig Mack's Bad Boy career. This would be Big and Craig's first and last collaboration on wax.

Letting Biggie lead off the track could be classified as one of the greatest hip-hop fails of all time. By the time Craig rapped on verse two, listeners were still focused on what Big said. Seventeen years later many rap fans have no clue it's actually a Craig Mack song.

Big's booming voice and unapologetic tough talk eclipsed Mack's star, and proved he was the marquee act on Bad Boy. On “Flava,” Big sounded menacing and precise with every word and syllable, leaving timid MCs shaking in their boots.

In fact, due to Big's slight speech impediment, it sounded like he was unexplainably ethering The Roots (“Like the Roots, disappear, vamoose you're wack to me.”)—which was something Biggie denied and addressed in various interviews (he was actually saying “the Gooch.”). Biggie's entire verse was chock full of quotables, but none more potent than the still relevant: “Don't be mad, UPS is hiring.”

7. The Notorious B.I.G. "Kick In The Door" (1997)

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Producer: DJ Premier

Album: Life After Death

Label: Bad Boy

Over Primo's Screamin' Jay Hawkins–sampling Tunnel banger, Frank White came out with two guns blazing—"stay low," he advises, "and keep firing"—aiming at all detractors, foes, and those who chose to use disrespectful views on the king of NY.

Forced to defend his throne, Biggie asserted his dominance as the boss of the Big Apple. If it wasn't bad enough that Biggie had an entire coast at his neck, now rappers in his own city were attacking him too. Fellow Brooklynites OGC mocked Big in a video, while Rae & Ghost accused him of biting of Nas' shit. Heavy hangs the head that wears the crown.

How did Big Poppa respond? He threw bleach in Raekwon's eye (now he's brailin' it), and mocked the jealous with the first appearance of the hilarious mad rapper skit. He seemed to have the Wu and Nas in mind, claiming they'd studied Ready To Die, stolen his flow, not recouped on their albums, and dozens of other hilarious jabs.

Perfecting the art of the subliminal diss, Big's "Kick In The Door" had plenty of rappers looking in the mirror, questioning whether his shots were directed at them.

6. The Notorious B.I.G. "Hypnotize" (1997)

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Producer: Deric "D-Dot" Angelettie, Ron "Amen-Ra" Lawrence, Sean "Puffy" Combs

Album: Life After Death

Label: Bad Boy

"Hypnotize" was Biggie Smalls toasting to the good life. The triumphant first single off his double-disc answer to Pac's All Eyez On Me was a bright moment in an otherwise dark and gloomy period in Big's life. The drama with Pac had come to an unexpected, tragic end, and it was time to move on. It was a time to celebrate—but when the album finally dropped we were celebrating the memory of Biggie Smalls.

Yeah, Big was the King of NY, but on "Hypnotize" he brought the rest of the country along for the ride—shouting out players in Detroit, hoes in Philly, and Versace supporters in Miami and DC. Puffy played Big's hype man on the track, lacing him with those now-legendary "take that, take that" ad-libs. He squeezed first and asked questions last, leaving plaintiff's daughters tied up in Brooklyn basements. Sure Big liked to party, but it was always business first. And if the head was right? Well, you know the rest...

This song created a small riot when played during Big's funeral procession through his Brooklyn borough. The visual of Big's fans swinging off lamp posts, jumping on top of parked cars, and dancing on top of newspaper boxes is something we'll never forget. In good times or bad, no matter the occasion, "Hypnotize" still brings people to their feet and gets them dancing all these years later.

5. The Notorious B.I.G. "Unbelievable" (1994)

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Producer: DJ Premier

Album: Ready To Die

Label: Bad Boy

The chemistry between Biggie Smalls and DJ Premier was, for lack of a better term, unbelievable. Rocking over a sinister soundscape and a slick Robert Kelly sample, Big left the track on crutches. "Live from Bedford Stuyvesant, the livest one" was damaging dumb rappers and bruising all sorts of egos along the way.

Biting his tongue for no one, Big was quick to diss a subpar MC. The random shot he fired at Kwame (“Your life is played out, like Kwame and the fuckin' polkadots”) effectively derailed the rapper's career until the 2000's when he returned as a producer with a new name.

4. The Notorious B.I.G. "Big Poppa" (1993)

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Producer: Chucky Thompson, Sean "Puffy" Combs

Album: Ready To Die

Label: Bad Boy

Although much of Ready To Die focused on gritty street tales of the trife life, you wouldn't have known it from the singles Puff chose to release. “Big Poppa” was the second look from the album, and it found B.I. playing the role of irresistible lover man. Although Big called himself "black and ugly as ever," he had enough big-man swag and personality to bag any cutie.

Over a perfectly flipped sample of the Isley Brothers' “Between The Sheets,” Big gave us a tutorial on the art of seduction, taking us through a night in the life of a bottle-popping, club-hopping Don Juan. He even shared life's three essentials: Money, hoes and clothes.

With “Big Poppa,” he successfully crossed over to the pop charts, further breaking down cultural barriers at a time when rap was just beginning to infiltrate Middle America.

3. The Notorious B.I.G. "Warning" (1994)

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Producer: Easy Mo Bee

Album: Ready To Die

Label: Bad Boy

With a position of power comes paranoia, and no artist revealed the downside of success quite like Christopher Wallace. Jealous ones do indeed envy—“Damn, niggas wanna stick me for my paper”—and Big made it evident that the envious may reside in your inner circle: “It's the ones that smoke blunts witcha, see ya picture, now they wanna grab the guns and come and getcha.”

“Warning” was a tale of backstabbing, murder, and mayhem. Big's captivating story kept listeners on the edge of their seats until the final moments, when two red dots appeared on the heads of Biggie's would-be assailants.

His ability to paint vivid pictures with words, only added to Biggie's larger-than-life persona. Frantic lines like: “I don't give a fuck about you or your weak crew/What ya gonna do when Big Poppa comes for you?” were said with such force and bravado that you believed them to be true.

2. The Notorious B.I.G. f/ Puff Daddy "Who Shot Ya?" (1994)

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Producer: Sean "Puffy" Combs, Nashiem Myrick

Album: Ready To Die

Label: Bad Boy

The shot heard 'round the world. What began as an interlude for Mary J. Blige—but deemed too violent for an R&B album—ended up inflaming the biggest feud in hip-hop history.

Released just two months after Pac was beaten, shot, and robbed of his jewels in a Times Square recording studio (where B.I.G., Puff & Junior Mafia happened to be recording upstairs), the track sent shockwaves throughout the industry—most importantly to Tupac Shakur, who was holed up in a cell at Clinton Correctional Facility, unable to retaliate with plenty of time to sit, listen, and dissect the lyrics.

While Big and Puff vehemently denied that the track was aimed at Pac, asserting that “Who Shot Ya” was recorded months before the shooting, some of the lines were a little too suspect to be written off as pure coincidence (“Brave nigga, turned front page nigga.”) If anything the record was poorly timed, and the fact that it was a mainstay in Biggie's live sets further fueled controversy.

Once Suge Knight sprang Pac from jail in '95, Pac went on the warpath, famously turning “Who Shot Ya” back on B.I.G. with “Hit Em Up”: “Who shot me, but you punks didn't finish...”

1. The Notorious B.I.G. f/ Total "Juicy" (1994)

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Producer: Sean "Puffy" Combs, Jean "Poke" Oliver, Pete Rock

Album: Ready To Die

Label: Bad Boy

“Juicy” was Christopher Wallace vindicated. The song served as the world's official introduction to The Notorious B.I.G., an unlikely rap star who conquered the mean streets of Brooklyn to turn his life from negative to positive. We'd already heard a few grimy tracks from Biggie, but this glossy first single off Ready To Die was his true coming-out party.

Cleaned up for the world to see, Big gave us a first-hand account of transitioning from life in a one-room shack, to having two rides and a limousine with a chauffeur. Even if the tale wasn't 100% accurate, you couldn't help but root for the big guy who'd gone from selling crack to feed his daughter to getting "up close and personal with Robin Leach."

Over a flip of Mtume's “Juicy Fruit,” Big's rags-to-riches tale warmed hearts across the globe—resonating with street hustlers and suburban kids alike. He truly spread love the Brooklyn way. And if you don't know, now you know.

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