Owen Wilson And Sheryl Crow
[ranking: 40]
Once upon a time, Hollywood made a movie called The Minus Man. This is where Owen Wilson met Sheryl Crow. Their relationship was met with a ??What?!?? from the media at large, but the two Texans dated from 1999 to 2001.
Crow went on to date Lance Armstrong, who would later date Wilson??s ex, Kate Hudson.
Bill Murray And Jenny Lewis
[ranking: 6]
A Page Six report in 2015 seemed to indicate actor Bill Murray was dating indie rocker Jenny Lewis. The two were reportedly seen together at the after party for Murray's 2015 film Rock the Kasbah.
Other sources said that the two were just friends, but it would be awesome if the rumors were true!
Jerry Hall And Rupert Murdoch
[ranking: 8]
Jerry Hall and Rupert Murdoch got married in 2016. They were 59 and 84, respectively. It's Murdoch's fourth marriage, but it's technically Hall's first, as her marriage to Mick Jagger from 1990 to 1999 was declared void by the British government.
Hall and Murdoch were first seen together at the 2015 Rugby World Cup Final between Australia and New Zealand.
David Spade And Julie Bowen
[ranking: 35]
Apparently, David Spade has serious game. He??s dated Heather Locklear, Nicolette Sheridan, Lara Flynn Boyle, and Pamela Anderson, and he has a child with former Playboy playmate Jillian Grace. He dated Julie Bowen in 2002.
Ryan Reynolds And Alanis Morissette
[ranking: 30]
Isn??t it ironic? Doncha think? Ryan Reynolds seems to have a type and Alanis Morissette refreshingly didn??t fit his later Scarlett Johansson/Blake Lively profile. Fans and media outlets couldn??t quite wrap their heads around the A-list actor and the more-popular-in-the-'90s singer getting engaged in 2004.
This was no fly-by-night celebrity couple, though. They stayed together for five years. Morissette said her 2008 album Flavors of Entanglement was inspired by the break-up.
Michelle Rodriguez And Zac Efron
[ranking: 29]
Michelle Rodriguez hooked up with Zac Efron in 2014 soon after she split with model Cara Delevingne. When Efron and Rodriguez appeared to be an item, the world had a meltdown with every major media outlet doing a collective double take.
Then, there was a huge wave of support, when media and fans alike were rooting for the couple. But it didn??t last.
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