21 '90s Celeb Couples You Totally Forgot Dated

Yep, Madonna and Dennis Rodman were once an item in 1994. As Madonna told USA Today (via Los Angeles Times) about the former NBA star, "I love Dennis Rodman. He's hot. I adore him. He's a rebel, the Madonna of the NBA." Their relationship appeared to be only a fling and nothing more.

Not only did they star in There's Something About Mary together, but starting in 1995, Matt Dillon and Cameron Diaz dated. Shortly after starring in the 1998 comedy together, they split. In July 2006, Dillon opened up to Parade about their romance and said, "I fell in love [with Diaz]. It's a very powerful thing when you feel that way about somebody. Cameron was a muse for me. I hadn't been in any deep emotional relationships."

While Gwyneth Paltrow was dating Ben Affleck (more on their relationship later), she introduced Affleck's BFF Matt Damon to Winona Ryder, according to Yahoo. They started dating in 1997 and broke up sometime in 2000. After their split, they both had nothing but good things to say about each other. In an interview with Black Book magazine in 2009 (via Yahoo), Ryder said, "Matt couldn't be a greater, nicer guy. I'm really lucky that I'm on good terms with him." As for Damon, he told Playboy (via Yahoo) in 2004, "My most recent relationships have not been with famous women, but I was with a very famous woman, Winona Ryder, for a couple of years, and we had a great relationship."

In addition to Winona Ryder, Matt Damon also dated Minnie Driver. They both starred in Good Will Hunting together, as well. In 1998, they split after Damon denied having a girlfriend on The Oprah Winfrey Show. Yeah, it's as cringeworthy as it sounds. Driver opened up to the Los Angeles Times in 1998 about it and said, "It's unfortunate that Matt went on Oprah. It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate."

In what might sound like a random relationship, Courtney Love and Ed Norton started dating after appearing in 1996's The People vs. Larry Flynt. They also got engaged for six months during their three-year relationship, but broke up in 1999.

How can you forget about Julia Roberts and Benjamin Bratt, especially since he accompanied her to the 2001 Oscars, where she won her first Academy Award. They dated for four years and seemed to be going really strong, when in June 2001 they split.

Before Portia de Rossi came into her life, Ellen DeGeneres dated Anne Heche. They were together for three and a half years, before calling it quits in 2000. It was a shock to many, especially since they seemed head over heels in love, wore matching wedding bands, and even called each other "my wife."

From 1997 to 1998, Mariah Carey and Derek Jeter dated. As People reports, their relationship made headlines and mainly because Carey was still married to her now ex-husband Tommy Mottola when they met. Per Carey's spokesperson, they broke up due to "media pressure".

Not only did Julia Roberts and Kiefer Sutherland date, but they were engaged. However, in June 1991, Roberts called off the wedding three days before the nuptials. According to People, on what was supposed to be their wedding day, Roberts found comfort in actor Jason Patric.

This is one relationship you may not recall at all, but Courteney Cox and Michael Keaton dated. They weren't together for a short time either, but were a couple for over six years. In 1995, they split. That same year, the former Friends actor told People about Keaton, "It's the most important relationship I've ever had, and I think he's the most wonderful person I've ever met."

After starring in 1995's Seven together, Gwyneth Paltrow and Brad Pitt started dating. They were together for sometime, but broke up in 1997. While chatting with Howard Stern in 2015, Paltrow said about Pitt, "I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt." She also admitted that she "was such a kid" at the time, which factored into their split.

Like her relationship with Brad Pitt, Gwyneth Paltrow and Ben Affleck were also once a popular couple after she split with Pitt in 1997. The broke up in 1999, then got back together, but then broke up for good in 2000. She also opened up to Howard Stern in 2015 about their former romance and said, "He was not in a good place in his life to have a girlfriend."

This may be one relationship that totally slipped your mind. Sarah Jessica Parker and Robert Downey Jr. dated for seven years. They first got together in the '80s and then went their separate ways in 1991. In a 2008 interview with Parade (via The Huffington Post) Downey admitted his former drug problem played a part in their break up. "I was so selfish," he said. "I like liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica, because it is the furthest thing from what she is. She provided me a home and understanding. She tried to help me. She was so miffed when I didn't get my act together."

In what may be the most random celeb relationship ever, Madonna and Vanilla Ice dated. After eight months together, they broke up in 1992. According to News of the World (via Digital Spy), the rapper ended things due to Madonna's table book Sex. He reportedly said, "But I broke up with her after she printed that book because I was hurt to be an unwitting part of this slutty package," he reportedly said. "It was disgusting and cheap. We were in a relationship yet it looked like she was screwing all these other people." Though, he also supposedly said dating the singer was "exciting" and called her "a great lover."

You read that right. New Kids on the Block singer Danny Wood dated Halle Berry in the late '80s, early '90s. It doesn't seem like it lasted long, but now you know the two were an item.

As E! News reports Ted Danson and Whoopi Goldberg got together during their 1992 film Made in America. After 18 months together, their romance came to an end in 1993.

In 2013, Alyssa Milano admitted to dating David Arquette. While chatting with Access Hollywood, she said she was about 19 when they dated. Other than that, not much is known about their relationship, which just might make it so forgettable.

That's right, Ashton Kutcher and January Jones dated from 1998 to 2001. In a 2009 chat with GQ, Jones did not have nice things to say about a former boyfriend and GQ claimed she was talking about the That '70s Show actor. "The guy I was dating when I first got to L.A. was not supportive of my acting. He was like, 'I don’t think you’re going to be good at this.' So — f*ck you! He only has nice things to say now — if anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated."

The director and comedian dated in 1994. According to an interview Cho did with The Hudson Union Society, they met at a bar called The Snake Pit and she was won over by his access to over 8,000 VHS tapes. Yep, that’s pretty ‘90s.

These two definitely made headlines for their relationship. Who can forget about Cindy Crawford and Richard Gere? In 1991, the two got married. Crawford was 26 at the time when she said "I do" to the then 42-year-old actor. However, their marriage came to an end in 1995. In 2016, the model opened up to People about their relationship and said, "I think part of the problem in our relationship was that we were a lot of other things, but I don't know if we were ever friends – like peers, because I was young, and he was Richard Gere." She added, "And then, as I started kind of growing up and growing into myself — it's hard to change the nature of a relationship once you're already in it."