WTF Celebrity Relationships You Wouldn’t Expect

WTF Celebrity Relationships You Wouldn’t Expect

It's understandable why celebrities constantly seem to only date other celebrities. When you're gorgeous, rich and constantly flying to romantic locations, you tend to gravitate toward people who check off at least two of those boxes.. Or at least, it's understandable most of the time, because when you look back across history, there have been some celebrity pairings that cause us to elicit a weird, strained "Huh."

Tupac and Madonna

In March 1994, Madonna made an appearance on Late Show With David Letterman that ranks as the cringiest thing Madonna has ever done -- which we're sure you'll agree is a pretty high bar. We could recount all her escapades, but honestly, where to begin? With the part where she pulls out a pair of panties and asks Dave to sniff them? With her sexualizing a microphone? With her lowkey bragging about trying "endo?" With her constantly dropping f-bombs and refusing to leave the stage when her interview was over? It was a parade of awkwardness.

In 2015, Madonna finally explained what happened that fateful night. Basically, she was having some guy trouble. Her then-current boyfriend, as she explained to Howard Stern, had got her "all riled up on life in general," so when she went on the show, she was feeling "very gangster." Which is fair considering that at the time, she was dating none other than Tupac.

Yes, THAT Tupac.

It isn't known when Madonna and Tupac started dating since they kept their relationship a secret, but what IS known is that this wasn't just a fling. The pair had major feelings for each other; a fact we only know because in 2017, a three-page letter from Tupac to Madonna went up for auction.

The letter, which was written in 1995 while Tupac was doing time, talks a lot about the pair's relationship and his own insecurities -- including the fact that throughout their relationship, he ("a young man with limited experience") was intimidated by Madonna's sexually-aggressive public persona. The letter also sheds some light on why the two broke up. Basically, it came down to the fact that although going public with their relationship would've helped her career, it would've not only hurt his, but (in his mind's eye) "be letting down half of the people who made ."

Luckily, Madonna still seems to celebrate the late rapper's birthday on Twitter, complete with TWO cake emojis. It's a sentiment too beautiful for words.

Dolph Lundgren and Grace Jones

The phrase "power couple" gets thrown around a lot these days, often in the context of describing two middling celebrities who care more about branding than each other. For an example of a true power couple, you have to go back to the 1980's and check out Dolph Lundgren and Grace Jones.

In 1983, Dolph Lundgren was a chemical engineering student with a full ride to MIT, a penchant for bodybuilding, and a side-career as a bouncer. That is, until he bumped into musician, supermodel, and actress Grace Jones while working security at one of her shows. The two swiftly became lovers and at her insistence, he landed a small henchman role in her latest movie project, A View To A Kill ... and thereafter abandoned his studies, signed up for acting classes, and dove headfirst into the hedonistic wilderness that was New York City in the 80's, where alongside Andy Warhol, David Bowie, and Jones, he became a mainstay of the party scene.

Life with Jones was an adventure for the young, naive Lundgren. For one, this being the 80's, there were drugs. Lots of drugs. "Back then everybody in circle was doing heavy drugs - cocaine, crack and smoking weed," said Lundgren in an interview. "I didn't know anything about drugs, I was just training. This was before drugs were a menace to society, it was just rich people who were having fun."

Jones and Lundgren would also share their bed, sometimes with as many as five girls a night. By 1985, however, the realities of this particular aspect of their lifestyle were wearing on Lundgren, partly because he'd just landed his big role as Ivan Drago in Rocky IV and didn't have any energy to spare. "Sometimes she would bring a girlfriend home and then I'd have to get up for work the next day and that kind of thing. It's great in theory, but when you have to get up and fight Sylvester Stallone in the morning, it's not such a good thing."

After Lundgren hit the big-time with Rocky IV, the couple started to fracture and fall apart -- a rollercoaster which culminated in Grace turning up at Lundgren's hotel in the dead of night armed with a gun, to 'rescue' him from his manager. As Grace recalled in her autobiography:

"We turned up at the hotel, not to shoot anyone, but to make sure he came with us. We banged on the door of his room. Bang, bang, bang! I've got a gun! I'm screaming, "Let him out, you bastard!" It was as though Tom was holding him hostage and we had come to rescue him, hair flying, legs flailing, breasts heaving, guns flashing, music pumping. This was the kind of hysteria that took place in Los Angeles. In one of the many lives I never got to live, another Grace (one who never came true) shot Dolph there and then. And that was the end of the ballad of Grace and Dolph."

Fortunately for us, this didn't happen but the couple nonetheless decided to call it a day -- but not before Grace, in a final, literal coup de grace, spent three days cutting up and burning his clothes.

Kate McKinnon and Bari Weiss

Kate McKinnon is a comedy icon, but as with every big-time star, she's got some real turds in her closet. Ted 2? The Angry Birds Movie? Both terrible, soulless pieces of dross, albeit terrible, soulless, forgivable pieces of dross.

There's a turd in her closet, though, that defies reason, explanation, and forgiveness. She once dated Bari Weiss, the hack/columnist who christened the "Intellectual Dark Web," aka: that "oppressed" group of academics and public figures (including Jordan Peterson and Ben Shapiro) who earn millions of dollars every year writing articles about how female superhero movies are ess-jay-double-you propaganda aimed at getting men to cut off their own dicks.

In an interview with Vanity Fair, Weiss described how she first met McKinnon while studying at Columbia and how the two not only spent several years in an on-again off-again relationship, but still remain good friends to this day. Other than that, Weiss refuses to talk about the relationship, presumably because she's allergic to being cool or even remotely likable.

David Bowie and Ola Hudson

We expect rock stars to be wild, hedonistic vagabonds -- and David Bowie was no different. So it's not surprising that while filming The Man Who Fell to Earth, he started getting bone-happy with the movie's costume designer. That's just the sort of behavior you expect from someone who has a four-foot deep fur-lined sex pit in his living room.

The costume designer in question? Ola Hudson, the world-renowned costume designer who by this point, had outfitted music legends like John Lennon, Diana Ross, and Ringo Starr ... as well as given birth to a music legend of her own, one Saul Hudson.

Although that's probably not the name you know him by.

Scott Penner
Sorry to destroy the fantasy that the world's most heavy-metal-mom actually put "Slash" on a birth certificate.

That's right, David Bowie banged Slash's mom.

When Slash was 11, his mother moved from their ancestral home in Stoke-on-Trent, England -- home of fancy teapots, rubbish sailors, and some hack clickbait writer -- to Los Angeles, to be closer to the beating heart of rock and/or roll. Alongside designing costumes, Ola was neighbors with Joni Mitchell and David Geffen, designed album covers for Neil Young, and oh right, there was her "mysterious romance" (as Slash called it) with David Bowie. Although to be fair, that describes pretty much every relationship that David Bowie had.

It wasn't an easy relationship between Bowie and Not-Yet-Slash, though. "My mom dated Bowie right after my parents broke up," said Slash in an interview. "I hung out with him and his wife and their son, Zowie, when I was real young. I really didn't like him that much, because he was the new guy in the house. I was really resentful." We're betting that things didn't improve much after Slash walked in on the pair while they were naked, either.

Although the pair's relationship only lasted for three years, Ola kept in touch with Bowie -- and even asked him to step in when Slash was at the height of his drug problem. There's no word on how useful that intervention was, but Slash soon moved onto collecting snakes. We'll let you decide whether that's an improvement or not.

Adam Wears is (allegedly) a comedy writer. Want to read other articles he's written for Cracked? Click here! Want to follow him on Twitter? Click here! Want to check out his website? Click here!

Scroll down for the next article
Forgot Password?