Just when you thought Future and Drake would be the year’s most unlikely duo, an announcement came in about a forthcoming joint tape from the world’s most recognizable drill rapper and a pop/reggae artist whose last top ten hit dropped in 2009. Yes, Chief Keef and Sean Kingston not only linked up for yesterday’s “Murda Mook,” but will also share a full-length project that is bound to attract a ton of listeners out of sheer curiosity. Although this comes out of left-field, even by Keef’s zany standards, it’s far from the first time the Chicago star raised eyebrows with his collaborative decisions. 

First attracting attention for his grim, violence-minded tracks like “Bang” and “3Hunna,” these early tracks gave Keef a reputation that he’s still attempting to live down to this day. That image, coupled with his distinct stylistic deviations from golden-era hip hop (the auto-tune, the mumbling, the lack of #BARS), in turn made any collaboration he pursued outside of his drill scene seem more unexpected by contrast. These days he wields less of a shock factor– partially because he’s varied his sound, partially because he’s spawned so many imitators– but seems even more open to working with artists from every corner of the rap game.

Some former collaborators, like Future and Waka Flocka Flame, may hail from different cities, but the stylistic similarities between their music and Keef’s lessened the surprise of joint tracks, so they aren’t included on here. And while we’d love to include a Keef/Lady Gaga track on here, that rumored product still hasn’t surfaced anywhere. Still though, we’ve got a lot of bizarre pairings to choose from here. 

Note, these are ordered by the amount of unexpectedness– with #12 being the least unexpected and #1 being most unexpected.

Gucci Mane

Chief Keef's Most Unexpected Collaborations

One of Keef’s most frequent out-of-town collaborators, GuWop is also the only one on this list to have a joint tape with him (last year’s Big Gucci Sosa). While their respective styles aren’t that far off from each other, the regional and age gaps (they’re 15 years apart) makes for one of the more unlikely duos of the 2010s. Gucci was incarcerated shortly after they began “working” together, so it’s unlikely that they recorded the bulk of their music together, but despite that, they often seem to push each other out of their comfort zones. As evidenced by the two cuts below, this duo can do hard street cuts and softer, more melodic gems.

Soulja Boy

Chief Keef's Most Unexpected Collaborations

Both frequent targets of “real rap” heads, Soulja and Keef probably share more haters than they do fans. Their biggest hits (“Crank That” and “Don’t Like”) couldn’t be more different, but whether due to a mutual affinity for drugs, foreign cars or auto-tune, these dudes seemed to hit it off as friends and collaborators. After they first linked in 2012, some beef arose between them, but as evidenced by recent collabs, they seemed to have worked things out. 

A$AP Rocky

Chief Keef's Most Unexpected Collaborations

Rocky began his rise just around the same time as Keef, but their similarities end there. Especially from the perspective of a label executive, Rocky’s media-friendly, commercially viable career is everything that Keef’s could have been but isn’t, but the duo clearly found something to bound over on “Superheroes,” taken from this year’s Bang 3. First announced back in Spring 2014, the collab took a while to surface, but it was well worth the wait. 

Young Ravisu

Chief Keef's Most Unexpected Collaborations

If you’re asking “who??”, you’re not alone. Appearing on Finally Rich, Keef’s only true major label album, the virtually unknown teenage Polish producer was found one day by Keef when he searched “Chief Keef type beat” on Youtube. The track he produced, “Citgo,” wound up being one of the best-received on the album, and hardcore Keef fans still consider it one of his finest songs to date. 


Chief Keef's Most Unexpected Collaborations

Before it became certain that Jody Highroller’s whole career wasn’t just a joke, every new collaboration with an established rapper came as a surprise. What’s more, Keef was one of the first to put his stamp of approval on RAFF, doing so on the infectious 2012 jam “Cuz My Gear.” The result is a perfect blend of their styles, with Keef keeping up with Jody’s reference-heavy verse by being more intelligible than usual. 

Kanye West

Chief Keef's Most Unexpected Collaborations

Mr. West’s Drake-esque stamp of approval on “Don’t Like” wasn’t a huge surprise, as it was, after all, a Chicago anthem, and remixing it didn’t require him and Keef to step in the studio together. What was unexpected though, was his thoroughly un-Drake move of following up that hype-chasing co-sign with more collaborations. First Keef showed up on Yeezus’ “Hold My Liquor,” and then last winter, their long-awaited collab “Nobody” surfaced. I suppose that Keef and indie rocker Justin Vernon (who was also on “Liquor”) are the odder couple here, but without Kanye pulling the strings, that probably would’ve never happened. Ye came up making almost music that was almost the polar opposite of Keef’s, but as he began to explore more abrasive, unorthodox sounds, he found a great protégé in his fellow Chicagoan. 

Wiz Khalifa

Chief Keef's Most Unexpected Collaborations

Although he was among the crop of established stars that Interscope (not Keef himself) apparently tapped in the name of commercial success for Finally Rich, the peace-loving Khalifa was far and away the strangest match. He appeared on “Hate Bein’ Sober,” which also featured 50 Cent, but unlike nearly everyone else featured on the album, this wasn’t the last time he’d collab with Keef. The pair dropped the song “Rider” just about a year later, and although their chemistry is debatable, it’s cool that they maintained a working relationship after being forced together by a major label. 


Chief Keef's Most Unexpected Collaborations

Full of Mario sound effects, subterranean bass and chipmunk vocals, the Tyga-assisted “Now & Later” is one of the strangest tracks in Keef’s already-pretty-weird catalog. Conceived for the aborted Thot Breaker tape, the track features a pretty standard verse from T-Raww in its second half, but his mere presence on such a weird cut is surprising in and of itself. Chalk this one up to Keef spending more time in L.A.


Chief Keef's Most Unexpected Collaborations

While Kanye West also comes from a different era of Chicago rap than Keef, he’s historically shown an affinity for bringing younger artists into the fold. Twista, on the other hand, didn’t until recently. To many, he represents the exact opposite of Keef and his ilk: lyrical, quick-witted and razor-sharp, but the man himself clearly doesn’t share those views. Keef showed up on a bonus cut of Twista’s 2014 album Dark Horse, and although the veteran MC turns up the auto-tune for his verse, he still seems like a featured artist on his own track, not showing up until well into the second half. Despite the fact that he sounds somewhat like a fish out of water, you’ve got to commend Twista for showing love to his city’s younger talents. 

Mac Miller

Chief Keef's Most Unexpected Collaborations

This unlikely duo have collabed on not one, but two songs in the past two months. Miller first showed up on Keef’s gleeful Bang 3 cut “I Just Wanna,” and then Keef returned the favor on the GO:OD AM track “Cut The Check.” Fittingly, each sounded more in their comfort zone on their own project, but surprisingly, neither sounded like they were forcing anything. A former frat rapper and a former gangbanger hardly sounds like a match made in heaven, but with both of their sounds getting weirder, and both relocating to L.A., they seem to make a great team. 

Lil B

Chief Keef's Most Unexpected Collaborations

At times, Lil B has seemed like the rap game Dalai Lama, while Keef used to revel in violence and destruction like the Joker in Gotham. The argument could be made that their styles are similar (Keef’s definitely had some very based cuts), but philosophically, they once seemed polemically at odds with each other. One thing apparently led to another, Keef traded violent bars for benefit concerts, and B wound up on Bang 3 Pt. 2. “Irri” is a strange track, but what else would you expect these guys to connect on?

Andy Milonakis

Chief Keef's Most Unexpected Collaborations

Before this year, former MTV star Andy Milonakis’ rap career consisted of some hilarious webcam videos, a random one-off track with Lil B and a stint in the group Three Loco with RiFF RAFF and Dirt Nasty. After randomly meeting Keef in L.A. last year, Milonakis says he was eventually invited to Keef’s house, which in turn led to a studio visit:

“He was texting me from the booth, ‘Yo, you got something for this? You gonna come lay something down?’ I was like, ‘Oh shit, I didn’t know I was supposed to be writing.’ So I wrote a verse, laid it down, and he just kept hitting me up like that for every beat that came on. I ended up writing six songs with him that day.”

That session not only led to a lasting friendship between the two, but also several collaborative tracks, one of which even ended up on a Gucci Mane mixtape. As is usually the case with Milonakis, the line between serious and hilarious is blurred on most of these, but it’s absolutely crazy to hear him on tracks with two of the hardest street rappers in the game.