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Shocking Celebrity Couples You Never Thought Will Be Together

Thursday, Jul 7, 2022, 7:36 pm


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1.Zach Braff and Drew Barrymore

Drew Barrymore has dated some strange guys, hell she married one Tom Green. It looks like Ms. Barrymore's taste in men is the opposite from her taste in movie roles. Zach Braff seems like a good guy. Don't get me wrong "Scrubs" was a fine television program. It was so good it was on two networks! But he seems like he is not in Drew's league. If she wanted to date a funnyman she should have given Jimmy Fallon a shot. I mean come one they had some kind of chemistry in "Fever Pitch" I wonder when Drew was making that movie did it ever cross her mind that she was making a bad movie with the future host of the "Tonight Show" ?




2.Winona Ryder and David Duchovny

This couple is not strange and shocking because one is A-list (Ryder) and the other is B-list (Duchovny) they are strange because both have dealt with strange addiction in their lives. Duchovny is a recovering sex addict and Ryder as we all remember is a kleptomaniac. This couple would have gone the distance but I bet visits to the lingerie section at Macys would have been hard for both of them.



3.Colin Farrell and Britney Spears

Many people blame Kevin "K-Fed" for Britney's dissent into madness as do I, but we all must remember it started with Colin Farrell. That's right the Irish bad boy was the first post Justin Timberlake stop that the Britney Spears crazy train visited.





4.Teri Hatcher and Michael Bolton

One is a desperate housewife and the other is just desperate. Hatcher and Bolton do have one thing in common. They were both famous in the early 90's. After that there respective careers went off in different paths. Hatcher would go on to do "Desperate Housewives" the show that would define her career and Bolton would go on to do Starburst commercials. All in all I would say pretty strange couple.



5.Moby and Natalie Portman

Off the bat this couple seems odd. One is A- list Hollywood actor and the other is a vegan musician who was on the brink of irrelevancy five years ago. If one scratches the surfaces however this couple makes a lot of sense the more you think about it. Moby is all about trance and electronics music, and Portman had a scene in "Anywhere but here" with electronic music..yea I'm grabbing at straws they were a weird couple.





6.Olivier Sarkozy and Mary-Kate Olsen

I guess when you're a child star you mature faster than your non famous counterparts. It makes sense. Child stars are surrounded by adults all day everyday, so it's not surprising that 26 year old Mary-Kate Olsen would want to date an older man. The fact that her man is 17 years her senior is not the shocking part. What's shocking is that Oliver is the half brother of French President Nicolas Sarkozy. Crazy right?



7.Woody Allen and Soon-Yi Previn

Woody Allen Married the adopted daughter of his girlfriend of 12 years. If that is not a shocking and strange celebrity couple I don't know what is. Allen who is the king of Neurotic comedy did something that would only be conceivable in one of his movies. The strange part is that it's real life.




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8.Nick Cannon and Mariah Carey

One has been a star since birth it seems, and the other gained slow fame by being America's oldest teenager. From the start this bizarre couple looked like it had the staying power of white after Labor Day. So far it looks like the jokes on us. The couples have been together for a few years and have had twins to boot. It looks like these two might go the distance after all.



9.Michael Jackson and Lisa Marie Presley

This couple is without a doubt the epitome of shocking. No one in a million years could say that they say this one coming. People did not even know that Michael and Lisa Marie knew each other well enough to date let alone marry. The marriage was short lived but the famous MTV Video Music Award kiss will live forever.



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10.George Clooney and Stacy Keibler

These two make a gorgeous couple. Even going to the grocery store they look like they stepped out of a magazine cover. What makes this couple strange besides the fact Clooney is considerable older, Keibler is a former pro wrestler. That's right before stepping out on red carpets keibler was running the ropes and hitting people with chairs in the WWE.



11.Minka Kelly and Donald Faison

Off the bat Donald Faison is a bigger star than Minka Kelly. He has appeared in "Clueless" and the hit sitcom "Scrubs" while Kelly only has Friday night lights and a canceled remake of "Charlie's Angles" under her belt. The reason this is an odd couple is the fact that Kelly has dated perennial All-Star baseball player Derek Jeter. Jeter is a notorious playboy who has dated some of the most beautiful women on the planet. Just for that Kelly's stock rises and she is therefore out of Faison league.




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12.Chelsea Handler and 50 Cent

When you think of a celebrity couples you usually think a singer and an actress, or and athlete and a reality t.v. star but a comedian and a rapper? That is exactly what we got with the brief and the shocking odd couple that was Chelsea Handler and Rapper 50 Cent. The two went on a couple of dates and that was it. To think of what conversation ensued between the Sharpe tongue comic and the vulgar rapper.



13.Angelina Jolie and Billy Bob Thornton

Angelina Jolie has had a very strange road to the top. From her public spat with father John Voight to the borderline incestuous public kissing of her brother. After all that she slid in nicely to a relationship with fellow actor Billy Bob Thornton. The couple was weird from the start. One reason could be the age difference; another could have been their constant PDA'S on the red carpet and other places. It also doesn't help that Billy Bob is the poster boy for America's creepy uncle.



14.Courtney Stodden and Doug Hutchison

If there was a picture definition of "Creepy" in the dictionary I think this picture would be one of the candidates. The pairing of 16 year old Courtney Stodden and 51 year old Doug Hutchison is so far out of left field I would not be surprised if Barry Bonds was asked to officiate the marriage ceremony.



15.Andre Drummond and Jennette McCurdy

Simple story, boy likes girl, boy tweets girl, boy meets girl, boy gets girl. What's not so simple is that the Boy is a 7 foot tall NBA player and the girl is petite former Disney star. The couple was spotted on a shopping date in West Hollywood. According to they were buying a ladder so she could kiss him.



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