It’s easy to forget that Ted Danson once dated Whoopi Goldberg. Why? Because it was just so damn random, that’s why.
But they’re not the only odd celebrity pairing, not by far. We’ve rounded up just a few of the most bizarre celebrity couples in the history of celebrity-dom.
Tom Cruise and Cher
Yep. That happened. Tom Cruise dated a considerably older Cher back in the 80s, and the singer bragged that they even shacked up at one point.
Michael Jackson and Lisa Marie Presley
Who the hell could forget this bizarre hookup? It was as if they couldn’t even believe they were dating.
After the relationship, in 2007, Presley expressed her regret. She said in an interview with Marie Claire:
“My biggest mistake? Let’s see. How can I word this? Um. Well. Leaving my first marriage, for the person that I left it for — that was probably the biggest mistake of my life.”
Oprah Winfrey and Roger Ebert
I’m not sure why this one is so weird, it just is. When Oprah was just starting out, the two went on a couple of dates, though a relationship never truly blossomed. However, Ebert does credit himself with helping Oprah become Oprah. Apparently, he convinced her to try to start her own talk show. He definitely deserves a car.
Lance Armstrong and Ashley Olsen
Olsen was only 21 when she was caught making out with Armstrong at a bar in New York City. He was 36 at the time. Weird. Just weird.
Conan O’Brien and Lisa Kudrow
Kudrow was a stand-up comedian in Los Angeles and O’Brien a writer for Saturday Night Live when these two crazy kids got together. Kudrow said of their romance:
“He was really smart, really funny and he thought I was funny, but found we were better as friends.”
Moby and Natalie Portman
Remember when pretentious musician Moby dated the even-more pretentious Natalie Portman? Me neither! I had no idea these two were an item, but apparently, Moby joked about their May-December relationship pissing off a bunch of nerds:
“You don’t date Luke Skywalker’s mom and not have them hate your guts.”
Madonna and Dennis Rodman
Gee, I wonder why this didn’t work out? The couple had a two-month fling back in the 90s, and I can only imagine how tumultuous those eight weeks were. On the bright side, at least they could swap outfits.