Let's Remember Some Gossip: Ross Mathews Recalls Chelsea Handler and 50 Cent's 'Relationship'

Let's Remember Some Gossip: Ross Mathews Recalls Chelsea Handler and 50 Cent's 'Relationship'

Let’s Remember Some Gossip is a new series in which we revisit the juiciest gossip of yesteryear, with the celebrities who simply cannot forget it.

“The truth is that there’s usually some truth to gossip,” Ross Mathews, the television personality known for his time on The Tonight Show with Jay Leno, Chelsea Lately, Celebrity Big Brother, and currently, RuPaul’s Drag Race and Live from E!. “In my experience, when I see something in the press and see it behind-the-scenes, it’s pretty close in lining up.”

Mathews’s second book is entitled Name Drop, and so I assumed he would be down to do so—he laughs when I ask him about his favorite outrageous gossip story. “When it’s my friend, it’s tough to talk about gossip about them,” he explains over the phone from California. “I’m going to get in trouble if I do.” But he did have this delicious tidbit to share about a piece of gossip the world has surely forgotten: Chelsea Handler and 50 Cent dated. Or did they? Mathews said:

“Do you remember when it was rumored that Chelsea was dating 50 Cent? Here’s the deal, I can’t confirm or deny, but I will tell you this: one time I was at Chelsea’s house. There was a party. 50 Cent was there. Chelsea had a Ms. PacMan machine in her living room. I was playing Ms. PacMan against 50 Cent, and I think I beat him. Good thing Mrs. PacMan’s machine didn’t take quarters, because I’d have to borrow one from 50 Cent!
That was a long time ago—it was hilarious at the time and it’s hilarious now… I just love waking up every morning and thinking, “Which two rando celebrities could start dating today?” Right there, that is worth waking up for.”

A refresher: Exactly one decade ago, in 2010, Chelsea Handler and 50 Cent were dubbed an item by the celeb press—seemingly confirmed in the above picture taken on Halloween 2010 in Malibu, California, after the rapper and comedian were spotted canoodling at a bar in New Orleans a few weeks prior. Their relationship is rumored to have lasted a few months, and may or may not have ended because 50 Cent was upset that his never-confirmed-as-having-dated “ex-girlfriend” Ciara was going to be on Chelsea Lately. According to the rumor mill, Ciara was allegedly mad that he was dating Handler in the first place, and Chelsea was mad that 50 Cent told her they may be some issue with Ciara.

In the years since their rumored coupling, Chelsea and 50 have discussed dating one another. Chelsea went on the Oprah Winfrey Network in 2013 and spoke about their short but loving fling; that same year, 50 Cent went on Howard Stern’s radio show and said he gave her the nickname “Gator… because you wrestle a gator… If you don’t hold on to her, you’ll lose the whole place.” But because their time together was so brief, I can’t help but wonder if it was staged. In retrospect, it looks a bit too coincidental that Handler would go on Good Morning America in 2014 to talk about her book, titled the astonishingly tone-deaf Uganda Be Kidding Me, to prove she is not racist because she dates black men. A few months later, 50 posted topless pics of the comedian on his Instagram page, so make of that what you will. The truth isn’t out there.

This has been Let’s Remember Some Gossip.

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