Can You Believe They Ever Got Together? The 29 Oddest Celebrity Couples Of All Time

The boxer and the beauty! The world was shocked when Nashville star Hayden Panettiere was first spotted with Ukrainian fighter Wladimir Klitschko, who she is planning on marrying!

Rosario Dawson has dated several gorgeous actors and models, so it was a bit surprising when she indulged in a romantic relationship with much-older director Danny Boyle.

Lady Gaga is so over the top when it comes to her style and music, so it was interesting to see that she found a good romance with surfer dude Taylor Kinney.

Melissa McCarthy and Ben Falcone are such an odd couple, that their romance was sort of spoofed in the movie Bridesmaids.

Age clearly wasn’t an issue for Mary-Kate Olsen, who is dating much-older Olivier Sarkozy, the brother of the former President of France.

Adrienne Maloof has no problem hooking up with younger men! The Real Housewives of Beverly Hills star has been on-and-off with Rod Stewart’s son Sean.

Chelsea Handler is always out to shock people, even when it comes to her love life! The talk show host briefly dated rapper 50 Cent, after meeting him on her show.

It’s hard to believe that Jack Nicholson and Anjelica Huston were once an item!

Julia Roberts and Lyle Lovett were one of the most unlikely celebrity couplings, and apparently they both realized it shortly after they eloped.

Bad boy Jesse James definitely wasn’t the guy who everyone thought America’s Sweetheart would end up with, and Sandra Bullock learned this the hard way when he cheated on her with several women, including Michelle Bombshell McGee.

Christina Applegate was ‘dating down’ when she hooked up with the then-unknown actor Brad Pitt in the late 1980s and brought him to the MTV Movie Awards. She later revealed that she felt guilty for dumping him at the show, and leaving with someone else.

Diane Keaton and Al Pacino were Hollywood’s hottest on-again off-again couple in the 1980’s after meeting during The Godfather Trilogy, however the union couldn’t sustain Diane’s pressure to wed.

Ashley Judd and Michael Bolton once made sweet music together! The crooner and the actress dated in the late 1990s.

Before Heather Locklear sunk her claws into Richie Sambora, Cher dated the Bon Jovi rocker.

Years before he met Courteney Cox on the set of Scream, David Arquette dated Who’s The Boss star Alyssa Milano in 1991.

It’s hard to imagine Edward Norton and Courtney Love in a healthy relationship! After the duo met on the set of The People vs. Larry Flynt in the 1990s, they became one of the oddest couples in Hollywood.

More than just friends? Heather Locklear was linked to Tom Cruise in 1982, but despite spending a lot of time with the Top Gun hunk, the Melrose Place star claimed the relationship was purely platonic.

Before they were famous, Kelly Preston and George Clooney were live-in lovers! The duo dated in the late 1980s and she even purchased his famous pet pig, Max, as a gift for him.

Years before she fell for rocker Ben Harper, Laura Dern dated her Blue Velvet costar, Kyle MacLachlan, for four years.

Robert Downey Jr. and Sarah Jessica Parker were Hollywood’s hottest couple of the 1980s, dating for seven years.

Pretty Baby and the King of Pop? Brooke Shields has admitted that former flame Michael Jackson asked for her hand in marriage several times during their brief romance during the 1980s and their subsequent lifelong friendship.

Before he got engaged to Jessica Simpson’s best friend, Scrubs star Donald Faison dated Friday Night Lights fox Minka Kelly.

Halle Berry dated a New Kid On The Block? In her youth, the Academy Award winning actress romanced Danny Wood.

Fatal Attraction? Glenn Close and Woody Harrelson were one-time lovers.

Before he dated Naomi Watts and Michelle Williams, the late Heath Ledger was in a year-long relationship with Heather Graham.

It’s hard to believe that Julia Roberts and Kiefer Sutherland were once Hollywood’s hottest couple! The Runaway Bride ditched him days before their planned 1991 wedding for his pal Jason Patric.

David Spade has romanced the hottest women in Hollywood, including Modern Family star Julie Bowen in 2006.

Before Alanis Morissette, Scarlett Johansson and BlakeLively, Ryan Reynolds was in a relationship with 3rd Rock From the Sun star Kristen Johnston for a year.

Apparently Seal has always had a thing for supermodels! Before he married Heidi Klum, the singer dated Tyra Banks.