8.31. Robert Downey Jr.
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Sarah Jessica Parker and Robert Downey Jr
Well before Carrie and co, Sarah Jessica Parker dated Robert Downey Jr for seven years in the ‘80s, but his drinking and drug abuse put a strain on the relationship. “She provided me a home and understanding. She tried to help me. She was so miffed when I didn't get my act together,” he said. “Sarah Jessica would pull me out of a hangover, and we'd go pick out furniture together. She is a force of nature!"
7.92. Brad Pitt
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Brad Pitt and Sinitta
Singer Sinitta said Brad Pitt was “just a very cute boy” during their two-year love affair in the 1980s. In the end the couple broke up because maintaining a long-distance relationship proved too difficult. “I’d go over quite a lot but, at the end of the day, you want someone you can hang out with, not someone you’re always waiting for,” she said. We wonder if Angelina has that problem.
7.13. Winona Ryder
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Winona Ryder and David Duchovny
David and Winona reportedly got together in 1996 though the Californication actor doesn’t like to talk about it. "I was just good friends with Winona. I just don't like to talk about my personal life. It's an area I don't go into."
6.94. Gwyneth Paltrow
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Gwyneth Paltrow and Luke Wilson
After meeting on the set of the Royal Tenenbaums, Luke Wilson dated Gwyneth Paltrow for a year in 2002. The actor said he liked Gwynnie’s “goofy sense of humour”.
7.55. George Clooney
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George Clooney and Kelly Preston
Things were so serious between George Clooney and Kelly Preston that in 1988 they were living in a Hollywood Hills home with a potbellied pig called Max. Kelly went on to become Mrs John Travolta but George is still looking for Miss Right.
6.86. Heather Locklear
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Tom Cruise and Heather Locklear
In 1982, a fresh-faced Heather Locklear stepped out with Tom Cruise. The young couple seem to have kept things very innocent. "I don't think we kissed. It was more friends," Heather said of the romance.
6.47. Cameron Diaz
Picture of Robbie Williams
Cameron Diaz and Robbie Williams
Robbie worked his British charm on Californian beauty Cameron Diaz in the summer of 2003. The couple was spotted holding hands and kissing on a beach in Santa Monica, and the singer is even alleged to have taken the Charlie’s Angel star for some Go-Karting fun in Berlin.
6.48. Tom Cruise
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Tom Cruise and Cher
This unlikely couple dated in 1987 when Tom Cruise was just starting out in his career and Cher was at the peak of hers. The singer described the actor, who is 16 years younger than her, as “shy”, but admitted: “I was crazy for him”.
6.79. Brooke Shields
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Brooke Shields and Dean Cain
Brooke Shields found her Superman (at least for a while) in Dean Cain. The couple dated for two years while they were studying at Princeton, but remain tight-lipped about their time together.
6.610. Justin Timberlake
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Justin Timberlake and Fergie
JT and Fergie had a failed fling in 1996. "It wasn't a long-term serious relationship, so there's no bad blood," says Fergie. "He was 16 and I was 23…It was before he got real heavy with Britney."
711. Drew Barrymore
Picture of Zach Braff
Zach Braff and Drew Barrymore
In July 2007, Zach Braff and Drew Barrymore were in contention for Hollywood’s hottest couple after they were clocked making out in a New York nightclub. Nothing more came of it however and we were left wondering what might have been.
6.712. Shia LaBeouf
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Rihanna and Shia LaBeouf
Shia LaBeouf admitted that he briefly hooked up with Rihanna before they both hit the big time in 2007. The couple didn’t make it past their first date though because there just wasn’t any chemistry between them. “It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends,” Shia said.
6.913. Courtney Cox Arquette
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Courteney Cox and Adam Duritz
Not content with dating her Friend Jennifer Aniston, Counting Crows’ Adam Duritz moved on to Courteney Cox in 1995. Art imitated life as Adam wrote the song “Monkey” for the actress and she appeared in the band’s music video “A Long December”.
7.514. Joaquin Phoenix
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Liv Tyler and Joaquin Phoenix
There was an instant attraction between Liv Tyler and Joaquin Phoenix when they met in 1997 on the set of Inventing The Abbotts. "What can I say? We hit it off immediately. She`s a darling. I`ve said it over and over again. She`s just very real, right there, never like a movie star. She`s so genuine, and she doesn`t take herself too seriously. It shows in the work she does that her honesty stands out most," said the Gladiator star.
6.715. Christina Applegate
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Christina Applegate and Brad Pitt
Christina Applegate was briefly the object of Brad Pitt’s attention in 1988. Christina was famous for her TV show Married With Children but Brad was on the verge of hitting the very big time.
5.316. Lindsay Lohan
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Aaron Carter and Lindsay Lohan
Back when Lindsay Lohan was a clean-living teen, the actress dated baby-faced singer Aaron Carter. Unfortunately Aaron wasn’t as innocent as he looked, and hooked up with Hilary Duff behind LiLo’s back.
7.117. Colin Farrell
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Colin Farrell and Britney Spears
After Britney brushed off rumours that she and Colin Farrell were romantically involved, the naughty Irish actor sent her a T-shirt saying: “I slept with Colin Farrell and all I got was this lousy t-shirt”. Unsurprisingly the pair aren’t talking to each other.
818. Leonardo DiCaprio
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Naomi Campbell and Leonardo DiCaprio
Naomi and Leo allegedly hooked up for a brief affair in 1995 just before the actor’s star rocketed with the success of Romeo and Juliet and Titanic.
7.319. Reese Witherspoon
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Reese Witherspoon and Stephen Dorff
Lucky Reese has had a string of gorgeous men but before she got involved with Ryan Philippe or Jake Gyllenhaal, she was dating Blade hunk Stephen Dorff in 1994. We bet you didn’t know that!
6.420. Owen Wilson
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Sheryl Crow and Owen Wilson
Sheryl and Owen hooked up with Owen Wilson for three years when the actor had just started out in Hollywood. Things didn’t end well however, with Owen calling things to a quick end and the singer saying: “It felt catastrophic. I was pretty miserable.”
6.821. Keanu Reeves
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Sofia Coppola and Keanu Reeves
This pair were romantically linked in 1992 after Keanu Reeves was directed by Sofia’s father, Francis Ford Coppola in Dracula.
7.122. Ashley Judd
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Michael Bolton and Ashley Judd
Michael and Ashley remain close despite splitting in 1997. The actress credits the singer with helping her out of a deep depression."He's family and very sweet," she said.
5.523. David Arquette
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Drew Barrymore and David Arquette
Wild child Drew Barrymore had a romance with David Arquette in 1991 (don’t worry – way before he met Courteney). The pair then starred together in Never Been Kissed, which had to be a bit weird!
724. Jennifer Aniston
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Jennifer Aniston and Adam Duritz
Jennifer Aniston and the Counting Crows frontman hooked up for just a week in the 90s and Adam hinted that the relationship was doomed from the start. "Some people you really dream about dating. Then, when you get there, you think, 'Wow, this is not the vacation I thought it would be. This is not where I want to spend my vacation'."
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