Lyle Lovett and Julia Roberts It can be easy to forget that one of the unlikeliest celebrity pairings happened when America's sweetheart hooked up with the country crooner 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.
Cher and Tom Cruise
In 2008, Cher dished in several interviews, including one with Oprah Winfrey, that she dated Tom Cruise before he was a big star. She told "Entertainment Tonight" that the two dated sometime after "Risky Business" in 1983 but before "The Color of Money" in 1986.
Drew Barrymore and Tom Green While still just engaged, comedian Tom Green had a head-scratcher of a cameo in Barrymore's "Charlie's Angels." The cameo was only matched by the couple's romance. They would get married in June 2001, only to file for divorce in December 2001.
Michael Jackson and Pamela Anderson A source told the British tabloid The Daily Mirror in 2008 that the King of Pop and "Baywatch" babe Pamela Anderson had gone on a string of dates. "It was all arranged by their people in total secrecy, very cloak and dagger," the source said. Perhaps they bonded over their mutual interest in plastic surgery?
Scott Baio and Pamela Anderson Only slightly less strange than Anderson's relationship with Michael Jackson was her time dating Scott Baio while he was starring in the TV sitcom "Charles in Charge" in the late 1980s and early '90s. The pre-"Baywatch" fame Anderson even appeared on a 1990 episode of "Charles in Charge."
Lisa-Marie Presley and Michael Jackson Jackson himself had a tendency to defy expectations when it came to his romances. In 1994, he married Lisa Marie Presley, Elvis' daughter, just 20 days after her divorce from singer-songwriter Danny Keough. The kooky couple, who had first met in the 1970s when the then 7-year-old Presley attended several of his concerts in Las Vegas, left people squirming with their kiss at the 1994 MTV Video Music Awards. Despite their claims of happiness, the relationship fell apart two years later.
Nicolas Cage and Brooke Shields You could make an argument for Lisa Marie Presley's rebound marriage to actor Nicolas Cage in 2002, but instead we'll turn our attention to another of Cage's relationships, this one to Brooke Shields in the late 1980s. Although little is known about their relationship, the two dated for about a year.
Andre Agassi and Brooke Shields But while the Cage-Shields relationship seems a bit off, even more strange was the high-profile coupling between long-haired rebellious tennis star Andre Agassi and Shields. The two dated for six years before marrying in 1999, although they divorced just two years later. Of course, the relationship came after Agassi dated Barbra Streisand in the early 1990s, so it might rank as only the second oddest relationship Agassi had.
Angelina Jolie and Billy Bob Thornton While the matchup between Angelina Jolie and Billy Bob Thornton seems strange on the surface, it couldn't hold a candle to the couple's strange actions. Married between 2000 and 2003, the Oscar-winners became known for their eccentric displays of affection, which reportedly included wearing vials of each other's blood around their necks. Thornton later clarified that the "vials" were, instead, two small lockets, each containing only a single drop of blood. Which makes it only slightly less creepy.
Heather Locklear and David Spade The former "Saturday Night Live" star has dated his fair share of attractive women, including Nicolette Sheridan, Lara Flynn Boyle, Pamela Anderson and Teri Hatcher, but it is his brief relationship with Heather Locklear that is most impressive. The two dated after Locklear filed for divorce from Bon Jovi guitarist Richie Sambora in 2006.
Adam Duritz and Jennifer Aniston Counting Crows frontman Adam Duritz briefly dated "Friends" star Jennifer Aniston at the peak of their fame in 1995. However, he later told Us magazine that the relationship wasn't that serious and they had "never even slept together."
Adam Duritz and Courteney Cox 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.
Michael Keaton and Courteney Cox Cox's relationship with Duritz wasn't her first interesting matchup and wouldn't be her last either. Toward the beginning of her career, with just her star-making turn in the Bruce Springsteen video "Dancing in the Dark," a recurring part in the sitcom "Family Ties" and roles in movies such as "Masters of the Universe" and "Cocoon: The Return," Cox dated "Batman" star Michael Keaton. The couple dated from 1989 to 1995.
David Arquette and Courteney Cox 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.
Moby and Natalie Portman According to Moby, his brief affair with 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.
Ted Danson and Whoopi Goldberg While this pairing of actors wasn't too strange on the surface, it was the details around the romance that made the pairing odd. "Cheers" star Ted Danson became so smitten with co-star Whoopi Goldberg during filming of the 1992 movie "Made in America," that he divorced his then wife-of-16-years, Cassandra Coates, the next year. It was one of Hollywood's costliest divorces, reportedly costing Danson $30 million. Danson courted more controversy when he appeared in blackface at a Friar's Club comedy roast of Goldberg in the fall of 1993 and delivered a racially offensive monologue.
Gary Oldman and Uma Thurman 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.
Christina Hendricks and Geoffrey Arend The voluptuous redhead has viewers lusting after her on "Mad Men," while he 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.
Lance Armstrong and Ashley Olsen Before 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 Olsen, 15 years his junior, at a New York City bar.
Roger Ebert and Oprah Winfrey Back when the movie reviewer and the soon-to-be "Queen of All Media" were both starting out in Chicago, Ebert and 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."
Oprah Winfrey and John Tesh According to a 2010 unauthorized autobiography of Oprah Winfrey written by Kitty Kelley, John Tesh allegedly left Oprah broken-hearted in the 1970s when he bolted in the middle of the night from the apartment they shared in Nashville, Tenn.
Ryan Gosling and Sandra Bullock It's not unusual for two good-looking stars to meet on set and develop a romance. That's exactly what happened when Bullock starred with an up-and-coming 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.
Jesse James and Sandra Bullock 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.
Jack Nicholson and Lara Flynn Boyle The unlikely couple 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.
Brigette Nielsen and Flavor Flav Perhaps the best descriptions of the relationship between rapper Flavor Flav and actress Brigette Nielsen, best known for her roles in "Red Sonja," "Rocky IV" and "Beverly Hills Cop II" and for being Sylvester Stallone's ex, can be found in the titles of the reality show they met on, "The Surreal Life," and their subsequent spin-off reality show "Strange Love."
Billy Corgan and Tila Tequila 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.
Ryan Reynolds and Alanis Morissette They're both Canadian, so maybe the matchup wasn't so odd, but there's still something off about the singer-songwriter pairing up with 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 O'Brien and 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 improve partners tried dating for a while but "found we were better as friends," Kudrow said.
Johnny Depp and Ellen Barkin Sex symbol 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.
Robert Downey Jr. and Sarah Jessica Parker Both one-time bad boy Downey Jr. and "Square Pegs" actress Parker got their start as young actors, but that wasn't enough to overcome his alcohol and drug problems. The two met on the set of the 1984 drama "Firstborn" and dated for seven years. "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica, because it is the furthest thing from what she is," Downey Jr. later told Parade magazine.
Macaulay Culkin and Mila Kunis 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.
Madonna and Dennis Rodman The media couldn't get enough of the brief two-month affair between pop star Madonna and NBA bad boy Dennis Rodman in the early 1990s. The highly-publicized relationship kept the rumors swirling, including one that Madonna wanted to have Rodman's baby, before it fizzled out.
Courtney Love and Edward Norton 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.
Brian Austin Green and Megan Fox 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.
Amber Tamblyn and David Cross 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."
Jack White and Renee Zellweger 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."
Hayden Panettiere and Wladimir Klitschko 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.
LeAnn Rimes and Tiger Woods 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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