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9 of the creepiest celebrity relationships

By / 06.04.13
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Creepiest Celebrity Relationships

Hugh Hefner/Crystal Harris image by s_bukley/Shutterstock


Celebrities have a long and disturbing history of creepy relationships: Liza Minnelli and David Gest, Tom Cruise and Katie Holmes, Michael Jackson and Bubbles the Chimp. So it falls upon us, the guardians of culture and all things decent, to periodically remind everyone that these people are out there and holy shit, are they ever creepy. And while some of the kings and queens of creep have gone their separate ways, a new breed has arisen to take their place on the throne of disturbia. It's like Game of Thrones only with creepy old men and occasional incest, which I guess makes it exactly like Game of Thrones. And on that note, here are nine of the creepiest of these celebrity relationships.

Photo credit: Hugh Hefner/Crystal Harris image by s_bukley/Shutterstock

Hayden Panettiere and Wladimir Klitschko

Hayden Panettiere/Wladimir Klitschko image by Helga Esteb/Shutterstock


Recently, these two comically mismatched love birds got back together, which I’m guessing made Hayden’s gynecologist clutch his rosary beads and start praying that he doesn’t get lost in there once Wladimir does his thing. Yeah, that might sound distasteful, but damn it, just look at the two of them together. He’s like ten feet tall and she’s a Smurf. This would be like a gorilla mating with your kitten. It’s impossible not to marvel and then cringe when considering the logistics. Also, whenever they show a shot of them standing side by side, it looks like a proud dad taking his daughter to kindergarten. Tell me how this isn’t creepy.

Photo credit: Hayden Panettiere/Wladimir Klitschko image by Helga Esteb/Shutterstock

Heidi Montag and Spencer Pratt

Heidi Montag/Spencer Pratt image by s_bukley/Shutterstock


Okay, admittedly we’re stretching the definition of “celebrity” here a bit since I’m guessing these two are about three days away from pan-handling on the side of the road but they still show up to haunt our lives every once in a while so I’ll allow it. It’s hard to say who is the creepier of the two. Heidi has basically reconstructed her entire body of out of plastic in order to become essentially a living sex doll while Spencer has hung on like some ghoulish pimp, selling the scraps of his lady’s dignity so he can afford to stylishly groom those pubes he has pasted on his face. It’s just a sad situation. But hey, at least now we know what it would look like if a sociopath ever fell in love with a robot.

Photo credit: Heidi Montag/Spencer Pratt image by s_bukley/Shutterstock

Hugh Hefner and Crystal Harris

Hugh Hefner/Crystal Harris image by Helga Esteb/Shutterstock


Crystal Harris already ran away from Grandpa Hef once, leaving him at the altar and then giving interviews talking about how gross it was to touch his wrinkled prune of a body. (Oh and also complaining because Papa Hef only gave her a small allowance every week. Yeah.) But then Hef had her lassoed and hog-tied (with a rope made of money, no doubt) and brought back to the grotto where he made her his concubine once again. Look, Hef is an American icon and back in the Stone Age I’m sure he was quite the charmer, but these days I’m guessing spoon-feeding him applesauce and tickling him until he has an accident and starts crying and talking about the time he and Charlie Lindbergh danced the Foxtrot with Clara Bow isn’t really a turn-on. Call me crazy.

Photo credit: Hugh Hefner/Crystal Harris image by Helga Esteb/Shutterstock


Look, it’s hard for anyone to date one of the Olsen twins and not come across as creepy. It’s even harder when you look like you could be her father, which is how it appears every time she steps out on the town with Olivier Sarkozy, the brother of the former President of France. Granted, she could be dating Bob Saget or Uncle Joey (oh God, I probably just gave Ashley some ideas) which I think we can all agree would be just a tad creepier, but this isn’t much better.

Photo credit: YouTube/popCultured

Courtney Stodden and Doug Hutchison

Courtney Stodden/Doug Hutchison image by Helga Esteb/Shutterstock


Come on, this one is almost too easy, right? I mean let’s get the obvious right of the way first – she was 16 when they got married and he was 51. That’s pretty fucked up. But what takes it to an even creepier level of, uh, creep is that it’s so incredibly obvious that the whole thing is just one big attempt to capitalize on people thinking it’s fucked up. Courtney Stodden wants to be famous so bad that she doesn’t even care that the only reason she’s “famous” is because people think she and her relationship are grotesque freak shows. She’d bang a corpse on live TV if she thought it would make people talk about her for ten seconds. Then again, that’s basically all her marriage is anyway. To be fair to Doug, though, there is at least a small chance that he actually thought she was older than him when they first met. After all, she looks like she was constructed from old leather, cigarette butts, and regret.

Photo credit: Courtney Stodden/Doug Hutchison image by Helga Esteb/Shutterstock


The idea of Hulk Hogan banging anyone is pretty creepy, right? I mean, we’ve all seen bits and pieces of that sex tape. It’s like watching an old leather shoe in a clown wig suddenly gain sentience and start humping a lady. Terrifying. But what really makes this relationship creepy is that his new wife, Jennifer McDaniel, aside from appearing to be a She-Hulk, looks disturbingly similar to Hulk’s daughter, Brooke. And given that the Hulkster seemingly has a hard time not letting the pythons run wild all over Brooke every time she slaps on a bikini, it’s hard not to speculate that the only reason he married Jennifer is, uh, well… oh God, I think I need to shower in acid.

Photo credit: YouTube/Maximo TV

Celine Dion and Rene Angelil

Celine Dion/Rene Angelil image by s_bukley/Shutterstock


Lots of older dudes marry younger ladies, so why is this one especially creepy? Well, here’s the thing, not only is Rene Angelil Celine Dion’s longtime manager/Svengali/father figure, he first met her when she was 12. And he was 38. Yeah. That doesn’t mean that they got together then but on some level she is always going to be a little kid to him. That’s just how their dynamic formed. He was the old dude who served a paternal role in her career and she was the young ingénue that he guided and then eventually decided he wanted to bang. She was 12 when they met! Come on.

Photo credit: Celine Dion/Rene Angelil image by s_bukley/Shutterstock

Kim Kardashian and Kanye West

Kim Kardashian/Kanye West image by Joe Seer/Shutterstock


No. Just… no.

Photo credit: Kim Kardashian/Kanye West image by Joe Seer/Shutterstock

Woody Allen and Soon Yi Previn

Woody Allen/Soon Yi Previn image by s_bukley/Shutterstock


Like anything else could be number one. Woody Allen married his own step-daughter! On Father’s Day in 2012, Woody’s son Ronan – and Soon Yi’s brother - tweeted the following: “Happy father’s day – or as they call it in my family, happy brother-in-law’s day.” And there you have it.

Photo credit: Woody Allen/Soon Yi Previn image by s_bukley/Shutterstock

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TAGSArbitrary RankingsCeline Dion and Rene AngelilCourtney Stodden and Doug Hutchisoncreepy celebrity couplescreepy celebrity relationshipsfeaturedHayden Panettiere and Wladimir KlitschkoHeidi Montag and Spencer PrattHugh Hefner and Crystal HarrisHulk Hogan and Jennifer McDanielKardashiansListsMary Kate Olsen and Olivier SarkozyStrange celebrity couplesweird celebrity couplesweird celebrity relationshipsWoody Allen and Soon Yi Previn
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