They say opposites attract and it turns out there are way more mismatched celebrity couples out there than we thought. It's time to hop in TEN's time machine and take a trip down memory lane to some of Hollywood's most bizarre and weirdest romances. Get ready for some blasts from the past!
10. Drew Barrymore and Tom Green
It didn't take Canadian actor and goofball comedian Tom Green 50 First Dates to spark a romance with Hollywood sweetheart Drew Barrymore. The unlikely pairing reportedly started dating in March 2000, and after a publicity stunt to tie the knot on Saturday Night Live, the lovebirds eloped to the South Pacific to say 'I do' in March 2001. They remarried in July before family and friends in a ceremony in Malibu, California.
Green later admitted that his short-lived marriage of 163 days was "a crazy, whirlwind of a time."
"Drew is a wonderful woman, I love her very much," Green said in a statement. "I wish our marriage could have worked out, I wish her much happiness."
"Yes, it is true we have decided to part," said Barrymore in her own statement. "I love Tom very much. He has always been a great friend and that won't change."
It was Green's first marriage and Barrymore's second. She first walked down the aisle with bar owner Jeremy Thomas in 1994, and they ended their brief relationship 19 days later.
While we don't think Green inspired Drew to star in 2009 rom-com He's Just Not That Into You, we do reckon she wishes her romance to the former MTV star was scripted for a film.
Tom Green and Drew Barrymore arrive at the premiere of 'Donnie Darko' at the Egyptian Theatre October 22, 2001.
The couple at the premiere of Charlie's Angel's, in Hollywood, 22 October 2000.
Tom Green and actress Drew Barrymore (voice of Akima) arrive at the premiere of Twentieth Century Fox's 'Titan A.E.' at the Staples Center June 13, 2000 in Los Angeles.
9. Kylie Minogue with Michael Hutchence
The princess of pop and Australia's darling Kylie Minogue began dating one of the biggest rock stars in town, INXS frontman Michael Hutchence in the late 1980s, after the pair met at a swanky bash after the Countdown Awards. Minogue lasted two years with the musician, but sadly he left her for supermodel Helena Christensen in the early 90s. So much for Michael's track Never Tear Us Apart then!
The Can't Get You Out Of My Head hitmaker previously said that her former lover is responsible for so many of her life experiences saying, "Let's just say I was 21 and my eyes were open to the world.
"You want to experience everything and I couldn't think of a better person to, you know, take those first steps into the big wide world with."
The couple remained close until Hutchence died at the Ritz-Carlton hotel in Sydney, Australia in 1997 while under the influence of drugs and alcohol.
Kylie Minogue with Michael Hutchence in Sydney in 1990.
8. Rosario Dawson and Danny Boyle
They swapped loving glances while working on 2013's psychological thriller film, Trance, and started to date when production wrapped. The actress, who is 22 years his junior, previously revealed that she made the first move on the British director saying, "We were going to just go our separate ways" if she hadn't."
The pair dated from May-December and were said to have completely ignored each other during an awkward movie junket for Trance.
(L-R) Director Danny Boyle, actors Rosario Dawson, James McAvoy and Vincent Cassel attend the UK Film Premiere of 'Trance' at Odeon West End on March 19, 2013.
Rosario Dawson and director Danny Boyle attend the premiere of Fox Searchlight Pictures' 'Trance' in 2013.
7. Jack Nicholson and Anjelica Huston
It's hard to believe this pair were even an item, but they firmly established themselves as Hollywood's coolest couple back in the seventies. Huston lived with the As Good as it Gets actor in spurts from 1973 until 1990, with their on-again-off-again relationship lasting 16 years came crashing down in 1989, when Nicholson had a child with a woman 12 years his junior.
In her tell-all book Watch Me, the second instalment to the 63-year-old's 2013 book, A Story Lately Told, Huston said Nicholson constantly broke her heart, and revealed his refusal to marry her hurt even deeper because of his lack of commitment to her.
The city of love (or no): Jack Nicholson and Anjelica Huston (1984) in Paris
Jack Nicholson stands with Anjelica Huston at the Cannes Film Festival May, 1974.
6. Edward Norton and Courtney love
Before they were famous! They met on the set of The People vs. Larry Flynt in the 1990s and dated for three years before they went their separate ways. In 2010, Love hit out at her ex claiming he was the cause of her losing $300,000 in a fund he reportedly told to invest in. However, she has since tweeted that she was “wrong” and that she actually tripled her money, not lost it.
Courtney Love, Woody Harrelson and Edward Norton (1996) star in the movie 'The People Vs. Larry Flynt'.
5. Heather Graham and Heath Ledger
Surprise! The late Heath Ledger was in a year long relationship with Heather Graham (shocking we know). The couple met at a party in Prague, where Ledger was shooting A Knight's Tale, and she was filming From Hell. Ledger had just come out of a relationship, while Graham's two-year relationship with Edward Burns had ended. At one stage there were rumours circulating that the pair were engaged, with The Hangover star even travelling to Ledger's family home in Oz. An official statement said the actors remained "good friends" after the break-up.
Ledger tragically died in 2008 with US authorities saying the results of the post-mortem were inconclusive.
The late Heath Ledger and actress Heather Graham mingle at the premiere party for 'A Knight''s Tale' May 8, 2001.
Heath Ledger and girlfriend Heather Graham sit at courtside during NBA playoff game between the Sacramento Kings and the Los Angeles Lakers May 6, 2001.
Heath Ledger and Heather Graham kiss at the premiere of 'Say It Isn't So' in 2001.
4. Lisa Kudrow and Conan O'Brien
More than just friends?
Who would have that Lisa Kudrow and night-time talk show host Conan O'Brien would have hit it off. Apparently, the comedic lovebirds had instant sparks.
"He was really smart, really funny, and he thought I was funny," Kudrow said.
The two didn't date for long with Kudrow, adding: "but found we were better as friends."
Did you know this pair had hooked-up?
Conan O'Brien visits the Friends set
3. Nicolas Cage and Lisa Marie Presley
Return to sender! Elvis's daughter Lisa Marie Presely met actor Nicolas Cage at Johnny Ramone's birthday party in 2000. They filed for separation in November 2002, just a few months after they walked down the aisle in Hawaii. It took nearly a year and a half for them to officially end their marriage that lasted less than four months. Presley admitted that a "temper tantrum" led to their shock divorce, saying a blazing row they had at a movie premiere was a major factor to their split.
"We're both so dramatic and dynamic that when it was good it was unbelievably good, and when it was bad it was just a f****** bloody nightmare for everybody. It was just Mr Toad's Wild Ride," said Cage.
Lisa Marie Presley, daughter of Elvis Presley, and actor Nicolas Cage attend the Los Angeles Premiere of MGM's 'Windtalkers' at Grauman's Chinese Theatre on June 11, 2002.
Nicolas Cage and actress Lisa Marie Presley arrive at the premiere of the film 'Captain Corelli''s Mandolin' August 13, 2001.
Nicolas Cage and wife Lisa Marie Presley arrive at the Egyptian theatre for the sneak preview of the film 'Adaptation' in Hollywood, California 23 November 2002.
Joint 3. Chelsea Handler and 50 Cent
Well I'll be damned! We were puzzled to find out that Chelsea Handler and rapper 50 Cent once dated. The Chelsea Lately host said she went out with the In Da Club hitmaker for the craic, which is weird in itself.
"He's actually a lot different than you would think," Handler said. Of their odd pairing she commented, "I thought it was kind of amusing that I would even be with 50 Cent; I thought it was funny."
She even said her friends were feeling the love adding, "My friends all loved him, my friends fell in love with him. [Jennifer Aniston and Reese Witherspoon] loved that I was dating him. They were like, 'Chelsea, come on.' They were both laughing really hard at it… I mean, everyone was."
However, their relationship was short-lived and ended over another woman.
We dated for a couple months and then we had a falling out. One of his ex-girlfriends was coming onto my show. [He called me about it and] I was like, at my job. It was just so juvenile, I was at work.
"I hung up and I've never spoken to him again," said Handler, who concluded with this back-handed compliment for ex-boyfriend 50 Cent: "I do think he's a really nice guy and I think he's smart in a certain way."
2. Alanis Morrisette and Ryan Reynolds
Way before his lovely wife Blake Lively came on the scene, Ryan Reynolds was engaged to rocker Alanis Morissette. They crossed paths at Drew Barrymore's birthday party in 2002, and dated for two years before becoming engaged in 2004, but their relationship sadly ended three years after. She later admitted that her album Flavors of Entanglement was written about their break-up.
The news of their split was confirmed in a joint statement by their representatives read, "Ryan Reynolds and Alanis Morissette have mutually decided to end their engagement. They remain close friends and continue to have the utmost love and admiration for each other. They ask that their privacy be respected surrounding this personal matter."
Fast forward a few months and Reynold's had moved on to Scarlett Johansson and those two did tie the knot in September 2008.
Musician Alanis Morissette and actor Ryan Reynolds attend the Los Angeles Premiere of the movie 'Blade Trinity' at the Grauman's Chinese Theater December 7, 2004.
Actor Ryan Reynolds with Alanis Morissette at the premiere of 'Blade Trinity' after party held at the Level 7 club Hollywood and Highland on December 7, 2004.
Alanis Morissette and Ryan Reynolds attend The 2003 MTV Movie Awards held at the Shrine Auditorium on May 31, 2003.
1. Macaulay Culkin and Mila Kunis
Are we being Punk'd? It's hard to imagine Mila Kunis and Ashton Kutcher not being besotted with each other, so finding out that Mila was with someone else for almost a decade was a shock. The pair reportedly met and started dating in 2002 when she was only 19 years old.
Culkin and Kunis almost made it down the aisle before breaking up in 2011 and were together for eight years before parting ways. Rumour has it that the pair split because Mila, who was 27-years-old at the time, didn't want to settle down and start a family.
In 2009, Kunis said,"'Not to say that I don't believe in it, but it's just not something that's important to me. But I will have children. I'm too selfish to have them now, but when I do, I don't feel like I need to be married,"
Macaulay Culkin and Actress Mila Kunis attend Michael Jackson's funeral service held at Glendale Forest Lawn Memorial Park on September 3, 2009.
Macaulay Culkin (L) and actress Mila Kunis attend the launch of the 'uBid for Hurricane Relief' charity auction and benefit at the Empire Ballroom October 15, 2005 in Las Vegas.
Macaulay Culkin and Ukrainian-born American actress Mila Kunis walk on Main Street during the 2004 Sundance Film Festival January 19, 2004.
Laura Delaney
