The 7 Strangest Celebrity Hip Hop Couples

Serena and Drake may seem like they came out of left field...but hip hop has a history of bringing odd couples together.

By Sowmya Krishnamurthy

What’s love got to do with it? Rappers usually don’t admit to love—on or off wax--and rarely step out publicly with anyone special. Save for the rare celebrity power couple like Jay Z and Beyonce or Kim and Kanye, rappers like being (or at least publicly appearing) single. When they do fall head over kicks in love, the results can be…strange. How did you meet HER? What do you two really talk about? In light of surprise lovebirds Drake and Serena Williams, here are our favorite and weirdest hip hop couples. 

1.    50 Cent and Chelsea Handler

50 Cent brags about being a P.I.M.P. on his records but he forgot all about that when he dated Chelsea Handler in 2010. The streetwise rapper (who infamously got shot nine times) and the no-holds-barred talk show queen only dated for a few months and apparently he was a total sweetheart. "He's actually a lot different than you would think," Chelsea said to Howard Stern. "He's really sweet.” Chelsea explained that the two had a “falling out” when Curtis (that’s what she called him) flipped over his ex-girlfriend Ciara appearing on Chelsea Lately. "I was like, at my job," Chelsea said. "It was just so juvenile, I was at work." Respect the gangsta, 50.

2.    Diddy and Emma Hemming

Diddy has no problem bedding beauties and the mogul has been romantically linked to everyone from Naomi Campbell and Sofia Vergara to Leah Remini. In 2000, then-Puff Daddy and J. Lo publicly called it quits (amid his criminal trial). He followed his famous flame with English model Emma Heming, who he posed with in a very provocative Details shoot (NSFW!) They fizzled quickly but what’s weird is that Diddy’s homeboy, Bruce Willis, married her a few years later. 

3.    Nick Cannon and Kim Kardashian

It’s hard to believe there was a time when we didn’t know Kim Kardashian. Before she broke the Internet and before she famously dated Brandy’s little brother, Kim Kardashian was a total unknown…and Nick Cannon dated her. Back in 2006, the funnyman and the unrecognizable Kim dated and for whatever reason, he keeps talking about this relationship (even posting throwback pics on his Instagram). Adding to the ick factor, Nick’s recently hinted that he may have smashed another Kardashian sister too.

4. Mariah Carey and Cam’ron

According to the rumor mill, Mariah Carey was not happy about ex-hubby Nick Cannon dating Kim Kardashian, but the songbird has her own romantic past. After her divorce from Sony honcho Tommy Mottola, Mimi went on a bit of a dating spree, hooking up with Yankees star Derek Jeter, Latin hunk Luis Miguel and rapper Cam’ron. Wait. Killa Cam? Yup. When they weren’t making sweet music on 2002’s “Boy (I Need You),” the two were heating up the streets of New York City with their fling. Then on  2015’s “Better Have My Money,” Cam confirms: “I ain't talking music when I say I did sh** with Mariah/Nick wasn't there, nor was Mottola.” 

5.    Big Sean and Naya Rivera

When Big Sean started dating Naya Rivera, everyone wondered how the totally unrelated stars met. Well, even big stars like to slide up in the DMs because the rapper hollered at the Glee actress on Twitter. Sadly, the social media fairytale did not have a happy ending. After getting engaged, things went sour fast. Big Sean dumped Naya, she accused him of stealing her Rolex and both moved on to other relationships.

6. Pharrell Williams and Jade Jagger

Moves like Jagger? Pharrell Williams has always been hush hush about his romantic moves but in the early 2000s, the eccentric producer had a cougar moment when he began hooking up Jade Jagger across the pond. Skateboard P and Mick Jagger’s daughter were an odd pair. The gossip rags loved to report about their on-and-off hookups and how allegedly, she wore him out in the bedroom.

7. Tupac Shakur and Kidada Jones

If there’s one rapper who has every girl’s heart, it’s Tupac Shakur. The star had it all—great music, handsome looks, a tortured soul—and at the time of his death, he was engaged to Quincy Jones’ daughter Kidada. Kidada was a music industry staple and Aaliyah’s bff. Pac made disparaging comments about Quincy and her sister, actress Rashida Jones, publicly blasted him for it. Yet, the pair somehow found love.

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