The Absolute Most WTF Celebrity Hookups of All Time

By Night Editor | July 8, 2014 | 4:30pm

Latest

On Monday, the fabric of society was shredded by a solitary photograph. When Zac Efron kissed Michelle Rodriguez on a boat in Italy, “Zachelle” was officially born (I voted for “Michfron”), inciting a frenzy of shocked fans who simply could not believe they were together.

The world seemed to stop spinning all because High School Musical kissed Blue Crush. Because no one saw it coming. She was supposedly with Cara Delevingne; he was supposedly too busy taking his shirt off to fall in love. Kreskin smoking PCP in a sensory deprivation tank wouldn’t have been able to predict those two as a couple.

Julia Roberts and Lyle Lovett

This is one of the earliest celebrity WTF couplings. In 1993, Julia Roberts was one of the world’s biggest movie stars, having come off a string of hits including Steel Magnolias, Pretty Woman and of course her groundbreaking performance as a gallerina/drug dealer mule on Miami Vice. She was also known as “America’s sweetheart,” which apparently means all you can you ever do for the rest of your life is wear pastel colored hoop skirts and tell stories about baking cranberry muffins.

But Roberts, being a real live human being and not some fembot cooked up in the imagination of Pat Robertson, wasn’t quite ready to play along with all that bullshit. So she married country singer Lyle Lovett in a small church in Indiana, while barefoot and wearing a long headscarf big enough that Voldemort could hide in it later.

People were completely gobsmacked that Hollywood’s “Pretty Woman” had wed a guy with curly hair. Let’s face it, that’s what everyone’s real problem was. Society cannot accept when someone with beautiful hair marries someone with bad hair. Think about it. I bet you’d rather see the world descend into a Waterworld-ish post-apocalyptic state than see Jennifer Aniston married to someone with frizzy hair.

Sandra Bullock and that gross mechanic Nazi guy

Sometimes your friends (or complete strangers who irrationally obsess about your private life on the Internet) try to tell you that the guy you are hooking up with is wrong for you. But you don’t want to listen because Paula Abdul and a dancing fucking cat once said “Opposites Attract,” so LALALALALALA I CAN’T HEAR YOU, HATERS. But Paula Abdul is completely full of shit and so is that cat.

Sandra Bullock found that out the hard way after she married “outlaw” glorified motorcycle mechanic and all-around shitty person Jesse James. This coupling was equivalent of that time when you were a little kid and wanted to have some Lucky Charms but there was no milk in the fridge. So you decided to use orange juice instead because you were a genius who figured out that juice tastes awesome and Lucky Charms taste awesome so obviously combining them was a no-brainer. ( How come mom never figured this out, you smugly said to yourself.) Everything was fine until the spoon hit your mouth then all your childhood dreams collapsed on your tongue. That “DEAR GOD WHAT HAVE I DONE TO MYSELF” moment when your taste buds became the Three Mile Island of flavor is exactly what Bullock experienced the second she realized she was married to a philandering asshole who had a thing for Nazis. This isn’t a guy who should be marrying one of the most bankable stars in Hollywood. This is a guy who should be convincing you to upgrade your motor oil brand at the Walmart Auto Center.

Tom Cruise and Katie Holmes

It’s easy to look back at all the couch jumping and accusations of brain washing and forget that these were just two crazy kids who spontaneously fell in love and weren’t trying bolster their own careers or anything. Watching their “love story” unfold was the equivalent of shotgunning a Four Loko and watching a Maya Deren film in reverse. People were more skeptical of this relationship than climate change deniers are of everything comes out of Bill Nye’s mouth.

Renee Zellweger and Kenny Chesney

When the news broke that Academy Award winner Renee Zellweger had married the NASCAR shirt with the sleeves ripped off known as Kenny Chesney, people were stunned. No, that’s not right. Everyone pretty much freaked the fuck out.

The story goes that Chesney saw Jerry McGuire and was so moved by the film he decided to write a song called “You Had Me At Hello.” You’ll know it as the song that made you cringe when your cousin picked it for the Daddy/Daughter dance song at her wedding. Four months later, he was married to one of the film’s stars because that is how life in Celebrityland works. If a guy wrote a song for me about a line from a Tom Cruise movie, I’d probably move to Tasmania and live in hiding to avoid the public humiliation of having to admit that’s how I was wooed. By the way, I unearthed several other heretofore unknown Chesney songs inspired by the blockbusters of Tom Cruise:

I Want the Truth But I Know You Can’t Handle the Truth
I Feel the Need For Speeding Up This Romance
Tame the Cunt, Tame It (THIS ONE IS SO ROMANTIC)

This is yet another case of we were right, famous people were wrong. Zellweger filed for an annulment from him citing “fraud” and everyone lost their shit all over again wondering if it was because he was gay. No, it was probably because she finally just listened to that song.

Emilia Clarke and Seth MacFarlane

No, no, no, Khaleesi, no, what are you doing? You must stay away from the Man of a Thousand Boob jokes. You are the Mother of Dragons. He is the guy who made a bulimia joke at the Oscars.

Ryan Reynolds and Alanis Morrisette

When the beautiful set of Canadian abs named Ryan Reynolds was reported to be engaged to alternative rock goddess Alanis Morissette, the 90s were officially declared dead. Somehow, the fact that that “You Oughta Know” was maybe written about Full House’s Uncle ~~Dave~~ Joey was way less disturbing than this. Alas, the coupling was not to be. Reynolds went on to marry impossibly beautiful human person Blake Lively and Morissette went on to write the album Flavors of Entanglement about their relationship, which seems like a lot of trouble to go through over the guy who was in R.I.P.D.

Sean Penn and Charlize Theron

True fact: When I saw the first headline about their relationship, I went to Snopes to make sure it wasn’t an elaborate Internet hoax. If Michelle Obama held a press conference tomorrow and said she was divorcing the president to marry the resurrected rotting carcass of Mussolini, I would be less horrified than I am by this relationship. The Cornballer seems like a more stable thing to be around than this coupling.

Adam Duritz and Everyone

Of all the great haunting mysteries of the universe (who built the pyramids, what happened to the city of Atlantis, who keeps greenlighting M. Night Shyamalan movies, etc.) perhaps the most perplexing is the mystery of why famous, beautiful women keep dating Counting Crows lead singer Adam Duritz. He makes Adam Levine seem like Rudolph Valentino. Because I CAN’T EVEN WITH THIS, here’s a list of all the women who have supposedly let the man one Jezebel staffer described as a “haunted Chia pet” touch them while naked:

Mary Louise Parker
Gwen Stefani
Lara Flynn Boyle
Emmy Rossum
Winona Ryder
Jennifer Aniston
Courtney Cox
Samantha Mathis

Flavor Flav and Brigitte Nielsen

This celebrity hookup was so utterly WTF it ended up being its own crazy reality show. They first met on VHI’s Surreal Life 3 and fell madly in love. They genuinely seemed to enjoy ~~doing lots of drugs and being on television~~ spending time together. It was like a relationship created by a six-year-old on an Etch-a-Sketch. It looks like a big, hot mess but when you take a step back, it’s actually kind of beautiful. Then you’re compelled to shake the shit out of it and pray that your brain will forever unsee what it was just exposed to. Actually, this might be one of the greatest love stories of all time. Fuck The Notebook; I’ll take Strange Love as my romance guidebook any day of the week.

Images via Pacific Coast News; Getty.