Friendships: Hollywoods Oddest Couples
By Chris Gardner

If Hollywood is a lot like high school, then it’s no wonder how we catch ourselves doing a double take when we see famous friendships crossing the typical clique lines. But instead of just shaking our heads, we decided to present the parade of pretty odd pairs to you in a real-life “The Breakfast Club”-style gallery of all the seemingly
misfit friendships of the rich and famous.

Call us crazy, but we were just plain shocked when we found out that Jennifer Aniston, one of the world’s biggest movie stars, had befriended Chelsea Handler, an admittedly boozy comedian who made a name for herself skewering celebrities on a late-night talk show. Weird, right? Not if you ask Aniston.

“I’m madly in love with the one and only Chelsea Handler!” Aniston said of the E! hostess while presenting an award to her at Glamour’s Women of the Year Awards in New York in 2011. “Chelsea Handler is not only one of the funniest and the brightest and the sexiest women on the planet. She is inspiring a generation of women to be bold and daring and express exactly what is on their minds, whatever that may be.”

Fine then, Jen — we’ll tell you what’s on our minds: All the other celebs with abnormal bonds. Keep clicking to see the unexpected BFF deets…

Charlize Theron and Kristen Stewart

Us Weekly reported in December that this duo, who co-stars in the upcoming “Snow White and the Huntsman,” had become “inseparable” on set. And it wasn’t memorizing their lines that brought them together. It was food! “They’re both really reserved, but they’ve had a few dinners,” the mag reported. “They’re serious cooks and
like to compare notes.” Theron stirred the friendship pot even more by adding this about Stewart: “We met on a plane going to Comic-Con. You know when you meet someone and it’s effortless? It was instantly amazing.” How sweet!

Jake Gyllenhaal and Adam Levine

The blogosphere seems to go nuts every time the “Brokeback Mountain” star steps out with the Maroon 5 frontman, calling their friendship a “bromance” and their lunch and dinner outings “bro dates.” But who needs labels when you can go straight to the source to find out what brought these two handsome gentlemen together in
the first place? “I’ve known this dude forever. He’s one of my oldest friends,” Levine told Out magazine. And there you have it.

Kim Kardashian and Demi Lovato

Despite a 12-year age difference, these two celebs must have found some common ground, as they’ve been known to be close for more than a year. Just last month, the pretty pair was spotted hanging out together at Beacher’s Madhouse at Hollywood Roosevelt Hotel. But their friendship is more than just a late-night affair. In a
letter celebrating Lovato’s February cover of Seventeen magazine, Kardashian wrote, “Demi, thank you for always being a true friend, for always following your heart, and for being an inspiration to me and countless other girls around the world.” Enough said.

Britney Spears and Mel Gibson

Remember when unstable Brit-Brit was spiraling in a seriously public meltdown a few years ago, and Gibson rushed to her side to offer help and support? We sure do! And apparently, so does the soon-to-be Mrs. Jason Trawick, because when Gibson recently suffered through some rough times of his own, Spears reportedly picked
up the phone to return the favor.

Kelly Osbourne and Miley Cyrus

On paper, these two couldn’t be more different. Osbourne hails from a hard-rock family with a checkered past that includes rehab and public outbursts, while Ms. Cyrus rose through the ranks as a Disney star genuinely proud of her Christian values and her country music-singing dad. But when the latter made the tricky transition from
tween queen to young adult star, she embraced a newfound rebellion — and rebellion is an adjective nearly synonymous with the Osbourne family name, hence their besties bond.

Elton John and Eminem

When these two teamed up to share the stage at Staples Center in Los Angeles for the 2001 Grammy Awards, it became the biggest story of the night. The collaboration helped cool the heat Eminem was feeling after falling under fire for allegedly homophobic song lyrics. But years later, a genuine relationship has formed from what started as an obvious ploy for positive publicity. John has even admitted that in recent years, he helped counsel the rapper through his struggle with substance abuse.

Tom Cruise and David Beckham

It’s hard to infiltrate Mr. Cruise’s inner circle, but all Beckham had to do was move to Los Angeles. When the world-famous soccer star transplanted his gorgeous brood to the city of dreams four years ago, Cruise and his wife, Katie Holmes, threw the Beckhams a lavish welcome party, and the guys have been good buddies
ever since.

Beyonce and Gwyneth Paltrow

Movie stars and music stars have been known to mix it up, but when B and G declared their BFF status, we had to say OMG. Beyonce was much more articulate about the whole thing. “She is what I strive to be one day. You go to her house and she makes you feel like you never want to go home,” the gorgeous singer gushed to
Harper’s Bazaar. The Oscar-winning actress had equally kind things to say about Jay-Z’s main squeeze: “She is the most talented human being on the planet.” Sounds like a complementary connection.

Jay-Z and Chris Martin

OK, so after knowing that Beyonce and Gwyneth are besties, it doesn’t surprise us that much that their significant others have struck up a friendship of their own. However, the Coldplay frontman admits that he still fields shock about his bond with the music mogul. “I think more people wonder why he’s friends with me. Of course,
I want to be friends with Jay-Z. He’s cool as f”“”“”“,” Martin told People. “In Britain, they’re like, ‘How are you friends with Jay-Z?’ It’s almost like they’re jealous. It’s the same with my wife: ‘How the f”“”“”“ did you manage to do that?’ And my answer is: ‘I have no idea.'”

Elizabeth Taylor and Michael Jackson

Their surprising friendship stood the test of time, spanning several decades and becoming one of the most enduring relationships. But what was it that brought these two legends together? Taylor said it best in a 1997 interview with Barbara Walters: “One of the reasons I think Michael Jackson and I are so close [is] because
neither one of us had a childhood, and we can relate to that and wonder at how we got by.”

George Clooney and Viola Davis

Fun fact: Current Oscar nominees George Clooney and Viola Davis are actually close friends. We weren’t the only ones surprised by that timely truth. The theatrical twosome shared the Jan. 13 cover of Entertainment Weekly which described them as “not an obvious pair.” These two have co-starred in three movies together —
“Out of Sight,” “Solaris” and “Syriana” — which led to a lasting friendship. And being pals with Hollywood’s most successful actor has its perks: Clooney let Davis and her hubby have his Italian villa all to themselves for their honeymoon.

50 Cent and Bette Midler

There’s been a lot of hullabaloo over the The Divine Miss M’s friendship with this infamous rapper. While we aren’t sure if the two are still in touch, we do know that their relationship grew out of a very good place: 50 Cent teamed up with the legendary entertainer when her environmental group, New York Restoration Project, decided to build a public garden in 50 Cent’s childhood neighborhood in 2009

Madonna and Rosie O’Donnell

Back in the day, these two besties turned heads for their surprise friendship, which really kicked off when they co-starred in 1992 baseball dramedy “A League of Their Own.” But O’Donnell declared that their friendly courtship actually started a year prior and that the circumstances were a bit more serious. “I had just seen ‘Truth or Dare,’
and she was the first woman that I met who had a similar situation to me,” Rosie has said. “My mom died when I was a kid, as did hers, and I’m named after my mom, as is she, and I don’t know anyone else who has gone to their mothers grave and seen their own name.”

Roger Federer and Anna Wintour

Anna Wintour is the biggest name in the fashion biz. Translation: She can pick and choose her BFFs. You might think she’d select a designer, a supermodel or a movie star, but you’d be wrong. She fancied a famous tennis player. Well, not just any player, but arguably the greatest tennis player to ever grace a Grand Slam court. Did we mention that he’s a dapper dude with one of the classiest off-court demeanors? Nicely played, Ms. Vogue

Oprah Winfrey and Gayle King

We kid, we kid. The end.

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