Ashton Kutcher settled down with a ’70s girl, but in the ’90s he was all about January Jones, whom we now know as Betty Draper, the ultimate ’60s housewife. The couple dated from 1998 to 2001 and it’s rumored that Kutcher had the gall to tell Jones that she was a bad actress!
Dillon and Diaz
Cameron Diaz may currently be in her honeymoon phase with new hubby, Benji Madden, but from 1995 to 1998 she was all about her There’s Something About Mary costar, Matt Dillon.
Barkin and Depp
Johnny Depp might win the official title of casanova of the ’90s. In 1994, he dated the amazing Ellen Barkin, who is now rumored to be dating Amal Clooney’s law colleague, whom she met at Clooney’s wedding.
Savage and Love Hewitt
In 1993, an adorable 14-year-old Jennifer Love Hewitt went on a date with Fred Savage, who was then 16 years old. According to Hewitt, it didn’t end well. “We went to a comedy club and we went to dinner and he dropped me off at home,” she told Wendy Williams in 2010. “He never called me again.”
Paltrow and Pitt
Brad Pitt and Gwyneth Paltrow met on the set of Seven in 1995, fell in love, were engaged by December 1996 and then broke up in December of 1997. Eighteen years later, we’re still obsessed with their matching haircuts and killer bone structure.
Johnny Depp, Kate Moss
Kate Moss was pretty much the definition of ’90s waif supermodel, so it made total sense for her to date bad boy Johnny Depp. “It was a nightmare,” Moss told Us Magazine in 2012 of her breakup with Depp. “Years and years of crying. Oh, the tears!”
Madonna and Tupac
We remember that Madonna was married to Guy Ritchie and to Sean Penn, but how did it slip our minds that the queen of pop was once with one of the greatest ’90s icons?
Madonna and Vanilla Ice
Yes, Vanilla Ice, aka Robert Van Winkle, says that he dated Madonna for eight months back in 1990 and she was a “great lover.” He also says he dumped her after she published the table book, Sex, because it humiliated him.
Keaton and Cox
Courteney Cox once told People magazine that Michael Keaton, whom she dated from 1989 to 1995, was a huge part of her life. “It’s the most important relationship I’ve ever had and I think he’s the most wonderful person I’ve ever met.”
Damon and Driver
They had amazing onscreen chemistry during the beloved ’90s film, Good Will Hunting, that transferred into real life. However, Matt Damon pulled a major no-no when he announced on The Oprah Winfrey Show that he wasn’t dating anyone before he let then-girlfriend, Minnie Driver, know.
Uma and Oldman
Not only did it slip by us that Gary Oldman and Uma Thurman dated in the early ’90s, but the couple was actually married from 1990 to 1992! “[It was] a mistake,” Thurman later told Vanity Fair.
Crow and Wilson
Sheryl Crow and Owen Wilson were an item during the late ’90s and he even inspired her to write the song, “Safe and Sound.” The couple also costarred in the 1999 film, The Minus Man.
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