For decades, celebrity couples have captured our imaginations, with fans rooting for many of them as they find love in the often hopeless world of Hollywood. But what about those couples that seem a little random, out of nowhere, and often, mismatched? From long-term relationships like Mariah Carey and Nick Cannon to short-lived flames like Madonna and Tupac, we’re breaking down some of the most famous Black celebrity couples that still have us scratching our heads.
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Mariah Carey and Nick Cannon
While we’ve known Mariah Carey and Nick Cannon as exes for years now, it’s easy to forget just how unexpected their reunion was initially. Yes, there is a bit of an age difference here, but more so Mariah’s fame was far greater than Cannon’s. Still, the two maintained their relationship for quite some time, and share two children together.
Halle Bailey and DDG
We’re still confused as to how Halle Bailey and DDG ever even came together in the first place. Halle, whose star only continues to rise, dated YouTuber and rapper DDG from around 2021 to 2025. While Bailey starred in some of the biggest films of late in “The Little Mermaid,” the drama between her and DDG seemed constant. The two share one son together, baby Halo.
Janet Jackson and Jermaine Dupri
From 2002 to 2009, Janet Jackson, one of the greatest pop stars of all time, was romantically involved with Jermaine Dupri. Janet was the first star to link up with a producer, but the entire situation certainly left fans confused, and it certainly helped Dupri’s celebrity-wise. At least we got some pretty great music out of it.
Whitney Houston and Bobby Brown
Whitney Houston and Bobby Brown were together for almost two decades, and spent so much of that letting us in to the highs and lows of their relationship (remember “Being Bobby Brown”?). They were together and making headlines for so long that it’s easy to forget just how out of left field their initial linkup was, as Whitney was one of the biggest pop stars in the world at the time, and had maintained a squeaky clean public image for years.
Lil Wayne and Lauren London
Lil Wayne and Lauren London dated on and off for years, and it’s still a connection that we’re wrapping our heads around. When speaking to Skin Deep about their relationship, London revealed, “We were in a relationship that didn’t make it. We tried more than once to revive it, and we were engaged briefly years ago, but we eventually parted ways,” she confesses.
50 Cent and Chelsea Handler
Yes, 50 Cent and Chelsea Handler briefly dated in 2010. The “In Da Club” rapper dated the comedian back in 2010, making for one of the most random linkups between a rapper and a comedian that we can think of.
Madonna and Tupac
From 1993 to 1995, Tupac and Madonna infamously dated, and we’re still shocked that these two dated, and that it was at private as it was for so long. While it was short-lived and long-rumored, the pop star finally confirmed the relationship back in 2015.
Kelis and Bill Murray
Yes, Kelis and Bill Murray were rumored to have dated. As we reported, the two were linked around 2023, with TMZ saying that the comedian and the singer were getting “close” while overseas in London. Murray has since come out and explained that the rumors around them were false, but that they “raised” his “cred” at the time, but still, for two years, the news of these two linking up had us all confused.
Lenny Kravitz and Nicole Kidman
Yes, Lenny Kravitz and Nicole Kidman dated and were even engaged back in the 2000s. In a full circle moment, Kravitz’ daughter Zoë starred alongside Kidman in “Big Little Lies.” In an interview, Kravitz explained, “I thought it was very interesting that they ended up on the same show. Zoë hadn’t seen Nicole since she was younger, and so it was beautiful that they got to know each other as adults and make this great show together.”
Jamie Foxx and Katie Holmes
Remember when Jamie Foxx was connected to “Dawson’s Creek” star Katie Holmes? The actor and singer dated the actress from 2013 to 2019 in what US Weekly described as a “low-key romance.” Random!
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