The 25 Best Dirty South/New York Rap Collaborations of All Time

From Killer Mike and El-P to Jay-Z and UGK.

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Complex Original

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Young New York rappers like A$AP Rocky and his A$AP Mob collective tout a brand of hip-hop that hews more closely in style and substance to Southern rap than most of their predecessors on the East Coast. It makes it easy to forget how strained relations between the regions have been at various points in rap history.

If it seems like there was always a steady line of communication between Southern, West Coast and Midwest artists, that's an illusion of hindsight. Relations between the South and the East could be cold at times, with some New York hip-hop luminaries having gone as far as categorically denouncing all Southern rap.

That doesn’t mean there aren’t exceptions, though. Some artists used their work to break down barriers, cross-pollinate audiences, and create hip-hop history. Jay-Z was taking Timbaland beats when New York thought it was too slick for the bounce, and artists like Nas have been quick to extend the olive branch to their Third Coast compatriots.

Here are The 25 Best Dirty South/New York Rap Collaborations of All Time, from improbable rapper team-ups to unexpected rapper/producer collaborations.

Written by Craig Jenkins (@CraigSJ)

RELATED: The 50 Best Atlanta Rap Songs

25. Dipset f/ Master P "Bout It Bout It...Pt. III" (2003)

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Album: Diplomatic Immunity
Label: Roc-A-Fella Records, Diplomat Records, Def Jam
Producer: Craig Lawson

"Bout It Bout It... Part 3" off the second disc of Dipset's 2003 Diplomatic Immunity album found Cam'ron and Jim Jones teaming up with No Limit's Master P to show some Harlem pride. The trio takes the opportunity to run down a laundry list of actual locations in the hood and the various criminal activities they're known for over sinister g-funk lifted off No Limit's first two "Bout It Bout It" installments.

24. Killer Mike "JoJo's Chillin'" (2012)

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Album: R.A.P. Music
Label: Williams Street
Producer: El-P

Dungeon Family alumnus Killer Mike and New York underground rap czar El-P met randomly through a mutual acquaintance in 2011, who suggested they work together. The collaboration quickly became R.A.P. Music, a whole album with El on beats and Mike on rhymes. El's clattering, futuristic boom bap and Mike's country drawl seemed like a weird mix on paper, but tracks like the bad-guy-wins story song "Jojo's Chillin" revealed a union as creative as it was improbable.

23. Prodigy f/ B.G. "Y.B.E." (2000)

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22. Busta Rhymes f/ Mystikal "Iz They Wildin Wit Us & Gettin Rowdy Wit Us?" (1998)

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Album: E.L.E. (Extinction Level Event): The Final World Front
Label: Flipmode Records, Elektra Records
Producer: Darrell "Delite" Allamby, Kenny Dickerson

Busta Rhymes met his fast rapping match on 1998's E.L.E. (Extinction Level Event): The Final World Front when he tapped No Limit Soldier Mystikal for "Iz They Wildin Wit Us & Gettin Rowdy Wit Us?" Mystikal leads with a monster of an opening verse, and Busta matches his speed and intensity with one of the fastest verses in a career full of lyrical speed trials.

21. Missy Elliott f/ Lil Kim & Mocha "Hit Em wit da Hee" (1998)

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Album: Supa Dupa Fly
Label: Goldmind, Elektra
Producer: Timbaland

The first song on Missy Elliott's hit debut solo record Supa Dupa Fly is "Hit Em Wit Da Hee", which introduced Missy as a capable switch hitter who could skip from rapping to singing and back without missing a beat. "Hit Em Wit Da Hee" also features Lil' Kim, who cuts through Timbaland's futuristic bounce with a half-serious, half-ridiculous one-liners about "gettin pissy in Bennigan's."

20. Lil Jon & the East Side Boyz f/ Bun B, Nas, Jadakiss, T.I., Ice Cube "Grand Finale" (2004)

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Album: Crunk Juice
Label: TVT, BME Recordings
Producer: Lil Jon

Lil Jon and the East Side Boyz united the West, East and South on their 2004 album Crunk Juice's closing track "Grand Finale." Jon drops a beat tougher than murder, and Bun B, Jadakiss, T.I., Nas, and Ice Cube proceed to lay waste to the track. All bars, no hook. Nas might've killed it, but Ice Cube turned in one of his more inspired performances in years ("I'm polished and gritty/Shoot better than that nigga who tried to kill 50").

19. Crooked Lettaz f/ Noreaga "Firewater" (1999)

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18. Cormega f/ Hot Boyz "Who Can I Trust" (1999)

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17. LL Cool J f/ Master P, DMX, Canibus, Method Man & Redman "4,3,2,1 (Remix)" (1997)

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16. 50 Cent f/ Young Buck "Blood Hound" (2003)

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Album: Get Rich or Die Tryin'
Label: Aftermath, Interscope, Shady
Producer: Sean Blaze

In its heyday, 50 Cent's G-Unit goon squad was a uniquely multi-regional coalition. You had 50, Tony Yayo, and Lloyd Banks from New York City, but there was also Game repping Compton (for the few months before the partnership with 50 exploded into a rivalry) and Young Buck from Nashville. In 2003, Buck and 50 linked up for the Get Rich or Die Tryin' album cut "Blood Hound" to hurl threats over producer Sean Blaze's Timbaland-esque thump.

15. Young Jeezy f/ Fat Joe and Jay-Z "Go Crazy (Remix)" (2005)

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Album: 12"
Label: Corporate Thugz, Def Jam
Producer: Don Cannon

"Go Crazy" was the third single off Young Jeezy's debut album Let's Get it: Thug Motivation 101. Don Cannon's sped up soul sample sounded like a lot of money, and Jeezy turned in a triumphant dopeboy anthem that somehow seemed repentant and celebratory at the same time. The remix turned the song into a multi-regional hustler's convention as Jay-Z and Fat Joe both contributed verses matching Jeezy's stories of the block brick for brick.

14. Jim Jones f/ T.I. and Bun B "End of the Road" (2004)

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Album: On My Way to Church
Label: Diplomat, Koch
Producer: Heatmakerz

"End of the Road," off Dipset capo Jim Jones' debut album On My Way to Church, overlayed a flayed, Janis Joplin-sampling beat with verses from Jones and Southern ambassadors T.I. and Bun B. The Heatmakerz' beat's too serious for games, and the three of them trade no nonsense verses without even bothering to devise a hook.

13. Jermaine Dupri f/ Jay-Z "Money Ain't A Thang" (1998)

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Album: Life in 1472
Label: So So Def, Roc-A-Fella
Producer: Jermaine Dupri

"Money Ain't a Thang," So So Def maestro Jermaine Dupri's classic 1998 collaboration with Jay-Z, began with Dupri listening back to Jay's Reasonable Doubt before a planned meeting between the two. Struck by the "Bouncing on the highway switching four lanes, screaming through the rooftop, money ain't a thing" line from "Can't Knock the Hustle," JD re-purposed the line into a chorus, looped up a funk sample underneath, and came out with a chart smash. Jay made it a hot line, Dupri made it a hot song.

12. Rick Ross f/ Nas "Triple Beam Dreams" (2012)

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Album: Rich Forever
Label: Maybach Music Group, Def Jam, Warner Bros. Records
Producer: J.U.S.T.I.C.E. League

Rick Ross' 2012 mixtape Rich Forever was packed with enough heat to have been sold in stores exactly as is, and the J.U.S.T.I.C.E. League produced "Triple Beam Dreams" is one of the tape's highlights. Nas jumps on verse one spitting straight acid, and Ross follows up with his trademark drug dealer supervillain bars. The pairing was a winning one: Nas and Ross had already squared off on "It's a Tower Heist" off 2011's Tower Heist soundtrack, and they regrouped soon after Rich Forever for "Accident Murderers" from Nas' Life Is Good album.

11. Scarface f/ Jay-Z & Beanie Sigel "Guess Who's Back" (2002)

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Album: The Fix
Label: Def Jam South, Island Def Jam, Universal Records
Producer: Kanye West

Houston rap legend Scarface always found time to collaborate with rappers from other regions, but his 2002 album The Fix seemed like a concerted effort to get out of his comfort zone. It featured production from industry heavyweights like Kanye West and the Neptunes and guest appearances by artists from across the country. Album highlight "Guess Who's Back" pairs Scarface with Roc-a-Fella soldiers Jay-Z and Beanie Sigel for drug kingpin posturing over diced up soul from Kanye.

10. Nas f/ Jadakiss & Ludacris "Made You Look (Remix)" (2003)

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9. Cam'ron f/ Lil' Wayne "Touch It Or Not" (2006)

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8. Gang Starr f/ Scarface "Betrayal" (1998)

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Album: Moment of Truth
Label: Noo Trybe, Virgin, EMI Records
Producer: Guru, Scarface

Gang Starr albums were largely New York-only affairs, but deep cut "Betrayal" off the back end of 1998's Moment of Truth paired Primo and Guru with Scarface. The song begins with a phone call between Guru and a friend on an up north trip who suggests they grab Face for a feature. Then Primo loops up an ethereal funk sample, while Guru kicks a rhyme about a family friend turned back-stabbing revenge killer, and Scarface mourns the life of a high school sports prodigy snuffed out over a brother's debt.

7. Slick Rick f/ OutKast "Street Talkin" (1999)

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Album: The Art of Storytelling
Label: Def Jam
Producer: Jazze Pha

Slick Rick's 1999 album The Art of Storytelling brought his classic sound up to date with help from producers Trackmasters, Ty Fyffe, and Dame Grease and guest raps from Nas, Raekwon, Snoop, and more. "Street Talkin'" blessed Rick with Jazze Pha production and a verse from Big Boi. Rick's smooth melodic flow was the perfect match for Jazze Pha's breezy production, and Big Boi's taut, verbose second verse offered a welcome counterpoint. OutKast and Slick Rick would pair up again a few weeks after "Street Talkin'" dropped as a single for Aquemini's "Da Art of Storytellin'," whose single version contains a Slick Rick verse woefully cut from the album.

6. Ma$e f/ 8Ball & MJG "The Player Way" (1997)

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Album: Harlem World
Label: Bad Boy Records
Producer: Mo-Suave-A

Mase's 1997 debut album Harlem World remains a monument to the gleeful materialism and squeaky clean production of late '90s New York pop rap, but things get a little gritty midway through the album when Memphis rap luminaries 8ball & MJG show up to toss around some tough talk. Ball & G's pimp tales and Ma$e's unrepentant displays of wealth proved a winning combination, and when Puff launched a Southern wing years later, he reached out to 8ball & MJG to be his flagship artists.

5. Jay-Z f/ Scarface & Beanie Sigel "This Can't Be Life" (2000)

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Album: The Dynasty: Roc La Familia
Label: Roc-A-Fella, Def Jam
Producer: Kanye West

Jay-Z got real a couple times on 2000's The Dynasty: Roc La Familia, both on "Where Have You Been," where he lashes out at an absentee father, and on "This Can't Be Life", where he, Beanie Sigel, and Scarface each spit tearjerker autobiographical stories about struggles and loss over a mournful Kanye West beat. The chemistry between the three is undeniable, and "This Can't Be Life" was the first in a series of collaborations including The Fix's "Guess Who's Back" and The Blueprint 2's emotional "Some How Some Way."

4. Devin The Dude "Doobie Ashtray" (2002)

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Album: Just Tryin' ta Live
Label: Rap-a-Lot
Producer: DJ Premier

Houston rapper Devin the Dude made a name for himself off sleepy and studiously druggy rap music years before "weed rap" entered the lexicon, and his ten-year run on Rap-A-Lot Records is full of underrated heat. "Doobie Ashtray" off 2002's Just Tryin' Ta Live is a laid back smoker's anthem with production from DJ Premier, who dials back his typical sample wizardry to let the funky sample loop here just ride.

3. Ruff Ryders f/ Drag-On & Juvenile "Down Bottom" (1999)

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Album: Ryde or Die Vol. 1
Label: Ruff Ryders, Interscope
Producer: Swizz Beatz

After a few guest spots on early DMX albums, Ruff Ryder Drag-On got his first major showcase on the Ryde or Die Vol. 1 compilation single "Down Bottom." Drag-On vaults out the gate with fierce double time raps almost entirely comprised of different ways he plans on shooting enemies. Juvenile slows things down in verse two, where he counters Drag-On's assault with a dash of melody and then scores the biggest, weirdest laugh on the record when he threatens to "Ruff Ryde yo ass then Cash in for Money."

2. Jay-Z f/ UGK "Big Pimpin'" (2000)

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Album: Vol. 3... Life and Times of S. Carter
Label: Roc-A-Fella, Def Jam
Producer: Timbaland

"Big Pimpin'" was Jay-Z's third Billboard Top 20 smash and an early indication that he might have some staying power as a solo artist. His trip to the upper echelons of the charts was aided by Timbaland, whose production folded Far East sonics into Southern rap, and UGK, who put on for Texas and started on their own path to national renown. "Big Pimpin" helped power Jay's Vol. 3 to triple platinum status and netted the whole team a Grammy nomination, and that's saying nothing of the profound effect it had on increasing the visibility of Southern rap for mainstream rap loving audiences outside the South.

1. OutKast f/ Raekwon "Skew It on the Bar-B" (1998)

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Album: Aquemini
Label: LaFace Records, Arista Records
Producer: Organized Noize

A chance meeting between Big Boi and Raekwon in Atlanta led to the recording of "Skew It on the Bar-B", the second single from the group's 1998 classic Aquemini. "Skew It on the Bar-B" is notable for being the first song Raekwon recorded with artists from outside New York, and Rae's appearance marks the first guest spot from an artist outside the Dungeon Family on an OutKast album. As a single, it didn't do too well on the charts, but was a critical favorite. Organized Noize's production had a distinctly East Coast flair, and the song went a long way in bridging the gap between Southern and East Coast rap fans.

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