Celebrity odd couples

It can be easy to forget that one of the unlikeliest celebrity pairings happened when America's sweetheart Julia Roberts hooked up with country crooner Lyle Lovett in 1993. The 27-year-old Roberts fell so hard for the 37-year-old Lovett that the couple were married just three weeks after meeting. The marriage broke up almost as quickly though, lasting less than two years.

But when Duritz and Aniston broke up, he wasn't yet done with the stars of "Friends." Duritz went on to date Aniston's co-star Courteney Cox in 1997, leaving him short a date with Lisa Kudrow from dating all three lead actresses on the sitcom.

Like Duritz before, Cox continued to show her interesting taste in men when she married her "Scream" co-star David Arquette in 1999. The couple would separate in late 2010, but remain friends.

According to Moby, his brief affair with Natalie Portman caused a lot of nerd wrath. "You don't date Luke Skywalker's mom and not have them hate your guts," he told Spin magazine in 2008.

Forget about the "Oprah Uma" introductions David Letterman made at the 1995 Oscars, the real question is who introduced Uma Thurman to Gary Oldman. Not only did the couple date, they were married from 1990 to 1992.

Voluptuous redhead Christina Hendricks had viewers lusting after her for seven seasons on "Mad Men," while Geoffrey Arend is known for his nerd-geek roles in movies such as "Garden State" and "(500) Days of Summer." Hendricks and Arend, who met at a party thrown by Hendricks' "Mad Men" co-star Vincent Kartheiser, married in October 2009.

Before Lance Armstrong's reputation was officially destroyed in 2013, it had already taken a dent or two in 2007 after the New York Post reported he was spotting making out with then 21-year-old Ashley Olsen, 15 years his junior, at a New York City bar.

Back when the movie reviewer and the soon-to-be "Queen of All Media" were both starting out in Chicago, Roger Ebert and Oprah Winfrey co-hosted the Chicago Emmy Awards in 1986 and went on two dates. In 2005, Ebert even jokingly took credit for some of Oprah's success, writing "Yes, it is true, I persuaded Oprah to become the most successful and famous woman in the world."

It's not unusual for two good-looking stars to meet on set and develop a romance. That's exactly what happened when Sandra Bullock starred with an up-and-coming Ryan Gosling in the 2002 psychological thriller "Murder by Numbers." The two, who are 16 years apart in age, dated for about a year before breaking up.

Of course, dating her much younger co-star could be considered an improvement over Bullock's decision to marry motorcycle builder and "Monster Garage" host Jesse James in 2005. The couple's marriage fell apart in 2010 amid reports that James had cheated on her with multiple women.

The unlikely couple of Jack Nicholson and Lara Flynn Boyle, who have a 33-year age difference between them, went public with their relationship at the 1999 Emmys. They proceeded to have an on-again, off-again relationship through 2006.

Who knows how long they dated or how serious the relationship was, but there's no doubt Smashing Pumpkins frontman Billy Corgan and reality TV star Tila Tequila went out once or twice. The two surprised rock fans when they attended Bravo's second annual A-List Awards in 2009, but stopped seeing each other soon after. By the end of the year, Corgan had moved on to dating Jessica Simpson.

They're both Canadian, so maybe the matchup wasn't so odd, but there's still something off about singer-songwriter Alanis Morissette pairing up with Ryan Reynolds, who went on to first marry actress Scarlett Johansson and then Blake Lively. Morissette and Reynolds announced their engagement in June 2004, but broke up less than three years later. Morissette has said her 2008 album "Flavors of Entanglement" was created out of her grief after the breakup.

Conan O'Brien and Lisa Kudrow met while he was still a writer for "Saturday Night Live" and she was working as an up-and-coming comedian in Los Angeles, according to the New York Daily News. The improv partners tried dating for a while but "found we were better as friends," Kudrow said.

Sex symbol Johnny Depp was briefly married in the early 1980s before becoming serially engaged to actresses Jennifer Grey, Sherilyn Fenn and Winona Ryder. He later had two successive four-year relationships with Kate Moss and Vanessa Paradis. But in between all that, he briefly dated "The Big Easy" and "Sea of Love" actress Ellen Barkin, nine years his senior, in 1994.

Considering they both started out as child actors, it's not too surprising that "Home Alone" star Macaulay Culkin and Mila Kunis, who rose to fame on "That '70s Show," started dating in 2002. Of course, the romance started long after Culkin had entered the "Where Are They Now?" files. The two ended up splitting in 2011, saying that the breakup was amicable and that they remain close friends.

You'd be hard-pressed to find a more unlikely couple than controversial rocker Courtney Love, the ex-wife of late Nirvana singer Kurt Cobain, and actor Edward Norton, but the couple dated for three years in the 1990s after appearing together in "The People vs. Larry Flynt." They were even rumored to be engaged before splitting up in 1999.

The relationship between "Transformers" beauty Megan Fox and former "Beverly Hills, 90210" star Brian Austin Green has been surprising people since the two first met on the set of the sitcom "Hope & Faith" when she was 18 years old and he was 30. Following years of dating, rumored breakups and false reports of engagement, the couple finally married in June 2010. Fox initially filed for divorce in August 2015, but by early 2016 the couple had gotten back together.

Most people probably didn't even know they were dating, but "Arrested Development" star David Cross and "Sisterhood of the Traveling Pants" actress Amber Tamblyn got married in October 2012 after nearly four years as a couple. Cross is nearly 20 years older than Tamblyn, who has also appeared in "The Grudge 2," "The Ring" and "127 Hours."

Oscar-winning actress Renee Zellweger and hipster rocker Jack White dated for a year-and-a-half after meeting in 2002 on the set of the Civil War drama "Cold Mountain."

While rising to fame as the NBC drama "Heroes," Hayden Panettiere started dating Ukrainian boxer and Heavyweight Champion Wladimir Klitschko in 2009. The couple overcame big differences in height (she's 5 foot 2 inches tall while he stands at 6 foot 6 inches) and age (she's 13 years younger) for two years before breaking up in May 2011. However, they later reunited and announced their engagement in October 2013. On Dec. 9, 2014, Panettiere gave birth to their daughter, Kaya Evdokia Klitschko.

Grammy-winning country star LeAnn Rimes and golf champion Tiger Woods "went out a few times" before she married her now ex-husband Dean Sheremet in 2002, according to Us Weekly. After the two went their separate ways, Woods tied the knot with Swedish model Elin Nordegren in October 2005, but his marriage fell apart starting in 2009 amid his highly publicized infidelity scandal.

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Celebrity odd couples