Frenemies: A History of 50 Cent and Jay-Z's Rocky Relationship

"Frenemies" is a term usually reserved for shit like the The Hills (and a song on Jim Jones' last album), but the rap game has its own collection of drama queens volatile, flip-floppy stars. Cases in point: the phony-friendship roller coaster that Jay-Z and 50 Cent have been riding over the last decade. No "Takeover" or "Ether" yet, but these two heavyweights still qualify as top-notch frenemies.

As regulars atop Forbes Hip-Hop list, you'd figure Jigga and 50 have enough in common to be buddies, but rap is a competitive sport and there's pretty much only room for one at the top. While they've never all-out beefed, they're not on that vegan steez neither—hence, frenemies. Check out our list of the friend and enemy moments between the two and a KRS-One video with his thoughts on a possible battle between 50 and Jay-Z...

50 CENT, "HOW TO ROB"
DATE: August 10, 1999
ENEMIES: With "How to Rob," 50 had barbershops buzzin' by sending shots at Jay and every other relevant rapper in the game. "What Jigga just sold, like 4 mil? He got something to live for/Don't want a nigga putting four through that Bentley coupe door." The plan worked, and has been copied by countless rappers since.

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JAY-Z ,"IT'S HOT"
DATE: December 28, 1999
ENEMIES: "I'm about a dollar, what the fuck is 50 Cent?" First freestyled at Summer Jam months earlier, Hov responded to "How to Rob" with this line off the track "It's Hot" from the Vol. 3: Life and Times of S. Carter album. Back then, 50 was only worth half a bar.

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50 CENT AND JAY-Z REEBOK AD
DATE: November 2003
FRIENDS: After 50 broke Billboard records with Get Rich or Die Tryin', he signed a shoe deal with Reebok. Turned out Hov had his own 'Bok deal for those S. Carters, so the new homies linked up for this commercial. Don't think Jigga and 50 were BFFs at the time? Peep the 16-second mark where they even took matching strides together. Or maybe Reebok execs carefully choreographed that corny moment. Dope ad, though—feels like a lot longer than six years ago.

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PARTY AT THE TAO IN LAS VEGAS
DATE: May 5, 2007
FRIENDS: It was a good year for Jay-Z and 50 Cent. They took number one and two (Jay-Z with $34 million and 50 Cent with $32 million) on the Forbes Hip-Hop Cash Kings list. Thirty million-plus would make friends out of any enemies, so when these two were spotted partying together at Tao in Vegas after the Mayweather vs. De La Hoya bout, it was no surprise. Note, however, the decidedly different outfits. Jigga-man's rich, so he took the doo-rag off. 50? Thug n'gga to the end.

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"I GET MONEY" BILLION DOLLAR REMIX
DATE: August 3, 2007
FRIENDS: As we mentioned, millions of dollars can do a lot for friendship and 50 was even better after getting that Vitaminwater guap, so he got Hova and Diddy to hop on the "Billion Dollar Remix" of "I Get Money." Was Fif actually bringing unity to New York hip-hop on this remix or just trying to bolster his chances in his SoundScan showdown with Kanye? Prolly the latter, but one thing we know for sure: He coulda spent a little more cheese on the CGI for this 12" art. It looks like The Game featuring a young James Earl Jones and Ray J.

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MADISON SQUARE GARDEN SCREAMFEST CONCERT
DATE: August 22, 2007
FRIENDS: Fans at the Garden were surprised to see Jay-Z bring out a slew of rappers including Diddy, T.I., and Kanye, but they were most shocked by the appearance of Curtis himself. Boo Boo looks like he's having too much of a good time in this pic—maybe that Formula 50 was spiked.

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FREEWAY'S FREE AT LAST ALBUM
DATE: November 20, 2007
ENEMIES: What started as a joint venture in which 50 and Jay were due to co-executive produce Freeway's Free at Last album ended up falling through at the last minute leaving Jay-Z as the sole executive producer. Even five prayers a day couldn't bring the two moguls together for this project.

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FLIGHT 187 VIDEO
DATE: September 3, 2009
ENEMIES: 50 took his first direct lyrical shot at Jay since "How to Rob" in his "Flight 187" track and video with the line, "Why Jay rockin' that Urkel look, man isn't he from Marcy?" and the hilarious GIF at 1:07. In following interviews, 50 Cent once again claimed that it wasn't a dis toward Jay. Just some "aggressive content," right Curtis?

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"NO ONE IS SCARED OF 50 CENT."
DATE: September 22, 2009
ENEMIES: After Kanye's case of logorrhea at the VMAs, Jay went on radio to defend his bay bro. When a U.K. DJ said he thought 'Ye would have acted a bit differently if it were 50 on stage, Jay responded with this classic quote. 50 quietly fumed.

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BEANIE SIGEL AND 50 CENT, "GO OFF"
DATE: November 13, 2009
ENEMIES: "You used to be from Marcy nigga, now you a 'Pass the Grey Poupon'-ass nigga." 50 teamed up with Jay's newly friend-turned-foe Beanie Sigel on "I Go Off," the Broad Street Bully's first official track since parting ways with the Roc. Fif let Beans be the lyrical assassin, providing only the hook and plenty of tough talk at the end of the track, where he gets at Mr. Knowles. And the saga continues...

BONUS: Krs-One On A Possible 50 vs. Jay-Z Battle

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