12 Oddest Celebrity Couples

We’re used to celebrity romances changing faster than Superman after Mexican food, but every once in a while the stars manage to surprise us with their strange alignments. Let’s review some of the weirdest matches in recent pop culture history and ponder the eternal question: WTF?

 

Anna Nicole Smith & Howard Marshall

Who says money can’t buy you love? Or at least one smokin’ hot blonde. Billionare tycoon and ancient pervert Howard Marshall put young up and comer (so to speak) Anna Nicole on the map. From there she took the world by storm and spent the rest of her short life on drugs, reality TV, or in court. At least Howard got his happy ending.

 

King Kong & Ann Darrow (Naomi Watts)

Like most little girls, I always dreamed a hulking beast would snatch me out the window & take me to reign over an island of dinosaurs & massive insects. Alas, these things only happen in fairy tales. The unorthodox romance between King Kong & his tiny human mistress/slave is a tale we can all learn from. I don’t know what, but something.

 

Ben Affleck & Jennifer Lopez

Did you think the world was going to just let this go, Ben-Jen? Just because you never had a catchy nickname like “TomKat” or “Brangelina” doesn’t mean we forgot or forgive. Your high-maintenance legend still wafts through green-rooms across Hollywood & New York City. It is said J. Lo used to demand everything in her dressing room be white, which is the only explanation we can find for her Ben affliction.

 

Ted Danson & Whoopi Goldberg

One has to wonder if this relationship began on a dare. They say that love is blind, and I guess this backs that theory up. We aren’t saying that Whoopi has all the sex appeal of a zamboni, but we are strongly implying it. Ted Danson we prefer to view as “mullet run-off,” his body a mere offshoot of his commanding hair.

 

Kermit the Frog & Miss Piggy

Moving from inter-racial to inter-species relations, who among us hasn’t been stumped by the intimate logistics of pig-frog lovin’? I know I’ve drawn many a diagram & I still can’t figure this out. In fact, for my 5th grade Science Fair, I even attempted to breed “Frigs” which suffice it to say, ended in numerous trampled frogs. It was scarring.

 

Lyle Lovett & Julia Roberts

If you’re wondering who the firetruck Lyle Lovett is, then you know how most of America felt when THE “Pretty Woman”– at the height of her fame – rolled out with this human ostrich. You can probably see that Lyle is a quirky musician. (Not to be confused with the famous crocodile.)  The pair had lots in common – like being famous & having huge mouths. Sadly, the couple has since divorced, or Julia ate him.

 

Peter Griffin & Lois Griffen (Née Pewtershmidt)

Only in the Magical Land of Television do fat, dimwitted, bastards like Peter Griffin land endlessly patient, fit, bright, loyal wives like Lois. Every time I see this show, I expect Lois to acquiesce to Brian’s advances. Yes, I know Brian is the dog. Have you SEEN Peter? I mean COME ON. He makes Jabba the Hut look like Mike "The Situation." 

 

Tom Cruise & Katie Holmes

As a devout follower of Gorlax the Omniscient Slug of Babylon, I find Scientology both ludicrous and offensive. That said, we here at Smosh are contractually obligated to pretend to tolerate all faiths. When Katie Holmes’ parents sold her as a child-bride to the Lizard People behind Scientology, they would’ve charged far more had they known she would end up belonging to Tom, a stage 45 some crap. He has a weird secret hat.

 

Michael Jackson & Lisa Marie Presley

My personal favorite unholy union has to be between the King Of Pop and The King’s daughter. I am reluctant to label this as an odd couple, because I would hate to imply any weirdness, however American musical royalty is so niche, they really are a band apart. For the record, I will bet all my kidneys that these two never had sex. In the end, Priscilla left because MJ kept trying to steal her nose while she slept.

 

Angelina Jolie & James Haven

Did you miss this extra special couple? You’d think it would be hard to select one from Angelina’s clown-car packed with lovers, but James has the stand-out feature of being her full-on biological brother. Yep, as in GROSS. Look at that picture again. They are totally kissing. I mean, ew. Peeps be all, “Oh, how did you two meet?” And Angelina’s like, “In the womb.” $h!t’s messed up.

 

Woody Allen & Soon Yi Previn

Speaking of family love run amok, our runner-up Most Freaky-Ass Couple has got to be New York’s frisky Great Uncle: Woody “Woody” Allen and his wife’s kid. What. An. Ace. Hole. Print a copy of this photo out & keep it in your wallet. Next time you are feeling low, especially if you’ve had your heart broken, pull it out and remind yourself: “At least I am not one of these ass-hats.”

 

Flavor Flav & Brigitte Nielson

Flavor Flav loves hats, ass or otherwise. But his favorite hat must be Brigitte. When it comes to the Grand Dame & Dumbass of our odd couples compilation, it is hard to summarize what is bizarre here with less information than your avergae graduate thesis in psychology. Instead, here is a list of what is NOT abnormal in this terrifying pair: both are carbon-based homo-sapiens. We think.

I could go on, but there’s an albino midget snake-handler that hangs out at the bar across the street at around this time, and I want to go slip him my phone number. Wish me luck.

 

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