10 Couples From The 90's That You Forgot Ever Happened

By Valerie Williams

Brad Pitt and Gwyneth Paltrow. Tom Cruise and Nicole Kidman. Cindy Crawford and Richard Gere. These are 90’s couples we will never forget, but what about the ones that were a big deal way back when and are all but forgotten now? These relationships happened and they mattered, ok? The fact that there was ever a time when Madonna and Vanilla Ice were a thing needs to be in the history books so our children and our children's children know all about it and can pass the tale down through the ages. Well, not really. But it's still fun to look back at the weird and unexpected couplings of everyone's favorite decade. Check out these couples of the 90's and see how many you've already forgotten about!

1. Johnny Depp and Kate Moss

This was the 90’s couple everyone was fascinated with – they smoked, they fought, they showed up at every event looking impossibly hip. When they were dating, Kate was at the very peak of her modeling career and Johnny was in just about every movie that mattered. They were together for about four years and a tabloid fixture in part because of wild stories about their romance, including the time Johnny trashed a hotel room after a fight with Kate. 

2. Matt Damon and Winona Ryder

Introduced in 1997 by Gwyneth Paltrow (who was dating Matt’s BFF Ben Affleck), this is one 90's couple everyone seems to overlook. They were together for a little over two years and after breaking up, Matt dated Penelope Cruz, which is the relationship everyone remembers. Winona, sadly, is mostly remembered for the oddball shoplifting incident shortly after parting ways with Matt.

3. Ashton Kutcher and January Jones

These two were together from 1998 to 2001 yet, I never heard about it until now. January is reported as saying that Ashton was not supportive of her acting and all but told her she wasn’t good at it. It would appear the world disagreed as she spent seven seasons playing Betty Draper on the critically acclaimed drama Mad Men. Good thing she ditched Ashton before he convinced her she couldn’t act!

4. Madonna and Vanilla Ice

Could this pairing BE more representative of the amazingness of the 90’s? It was brief, but these two superstars dated for a little while in 1990. Vanilla Ice reportedly had jealousy issues after the release of her infamous book, Sex, and they break up shortly after its release. There was no way this would last – she is the queen and he's….well, he's Vanilla Ice.

5. Julia Roberts and Lyle Lovett

The whole world wanted to know what a beauty like Julia Roberts saw in quirky country singer Lyle Lovett. They married in June 1993 after only a few weeks of dating, shocking everyone. Well, it couldn’t have been anything too compelling because they divorced almost as quickly as they decided to marry – after only 21 months of marriage.

6. Julia Roberts and Matthew Perry

Matthew and Julia dated briefly in 1996 after she appeared in a guest spot on Friends. It was at the height of both of their fame so the pressure probably made it difficult to stay together, but they were so adorable while it lasted.

7. Jennifer Love Hewitt and Joey Lawrence

It doesn’t get more 90’s adorable than J-Love and Joey. She had Party of Five, he had Blossom and together, they were a 90’s sitcom It couple for a short time. Jennifer is now married and pregnant with her second child and Joey is married with two kids but this is one couple I wish had stayed together because of their sheer cuteness.

8. Mariah Carey and Derek Jeter

Mariah and Derek dated in the late 90’s when Derek was at the height of his baseball career. This coupledom is often forgotten by everyone as Mariah is better known for her marriages to Tommy Mottola and Nick Cannon while Derek had a long-term relationship with actress Minka Kelly

9. Cameron Diaz and Matt Dillon

Cameron and Matt dated between 1995 and 1998. They reportedly parted ways because Matt wanted to start a family and Cameron wasn’t quite ready yet. It’s been 17 years and while she’s now married to Benji Madden, Matt is still single and never had kids. I wonder if he has been hung up on Cameron all this time?

10. Sheryl Crow and Owen Wilson

This one only includes the very end of the 90’s but is worth including because almost everyone forgets they ever dated. Shortly after they broke up, Sheryl ended up engaged to Lance Armstrong and that’s the relationship the world remembers. She did write a song about her and Owen on her album C’mon C’mon, so they will always have that.


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