The Best Couples from the '90s You May Have Forgotten About

Their love affair began at Witherspoon's 21st birthday party in 1998, where after meeting and spending the night talking, she reportedly told him, "I think you're my birthday present." (I mean, come on.) They were engaged a year later, got married in 1999 when Witherspoon was six months pregnant, and by the time they split in '07, had mini-me children Ava and Deacon.

File this under "The Most Amazing Couple You Forgot About/Didn't Know Existed." But Madge and Ice were legit for a whole eight months in 1992, until he dumped her for publishing her book Sex, which he found "disgusting and cheap." He also said that she's still the oldest woman he's ever been with. Why does this Vanilla taste so bitter?

Yes, this actually happened—and for three whole years from 1998 to 2001. But while they look super cute here, there were rumors that Kutcher is the ex who Jones said wasn't supportive of her acting. Hey, Ashton, have you watched Mad Men lately?

Can we theorize that it was Johnny Depp's mission to date every single poster girl of the decade? Before heroin/grunge-chic Kate Moss, it was Winona Ryder (albeit pre-Reality Bites). They met in 1989 at a movie premiere, when she was 17 and he was 27. And despite Ryder's young age, this wasn't puppy love—they got engaged in 1990 and remained so until they broke up in 1993. A word to the wise: Don't tattoo your SO's name on yourself. Depp's "Winona Forever" now reads "Wino Forever."

One of the more dashing couples in our lineup, these two were married from 1991 to 1995. They met at a barbecue at the home of the late, great photographer Herb Ritts when Crawford was 21. She went on to become the capital-S of supermodels in the '90s, and has said that success (and the age difference) put a wedge in the relationship.

We don't know much about these two, except for the fact that before Claire Danes left the Australian singer for actor Billy Crudup in 2003, they dated for six years.

First of all, Dillon's derp face in this pic is stellar. Secondly, the details: They started dating in 1995, but split three years later in 1998. Apparently, Dillon wanted to settle down, but after filming There's Something About Mary, Diaz wasn't ready for a family quite yet.

After meeting on the set of Seven in 1995, Gwyneth Paltrow and Brad Pitt were engaged by December 1996. They broke up six months after that, and I'm just a tiny bit sad that we'll never get to experience the blondest, most blue-eyed kids ever (though his kids with Angelina Jolie certainly won the gene pool lotto).

This is one of those couples that always maintained the "Oh, but we're just really good friends!" shtick, but word has it they were romantically on and off for a few years after meeting on the set of A Time to Kill. P.S. They're still good friends, and I believe them on this one.

These two dated for about a year after meeting on the set of Good Will Hunting, but apparently their breakup was...not so good. During an appearance on Oprah, Damon said that he was no longer dating anyone—and Driver learned about this sudden relationship status change when she tuned in with millions of other viewers.

No relationship is without its up and downs, and this rule certainly applies to the 13-year relationship between Grant and Hurley. The two started dating in 1987 and in 1995, Grant famously ran into a little trouble with someone named Divine Brown. Nonetheless, the pair lasted until 2000 before splitting amicably—so amicably, in fact, that Grant is godfather to Hurley's son.

The actors met on the set of Gattaca in 1997, married a year later, and had two children together before divorcing in 2004. It seems like they remain on good terms, though, if their casual hangout at Sundance is any indication.

While we saw a version of this relationship play out on the small screen when Donovan played Rachel Green's love interest, Joshua, on Friends, it turns out that the fictional romance occurred during the demise of their actual one. Aniston and Donovan began dating in 1995, and split up in 1998, right as the Joshua/Rachel storyline was in production. They were also rumored to be engaged at some point.

Never one to bite her tongue, Paltrow has since remarked that her relationship with Affleck, which lasted from 1997 to 2000, fell apart because they had "different value systems." The good news is, they've both moved on.

Yes, expect to see a few of the same faces in this roundup, since—haven't you heard?—people in the entertainment industry really like to date each other. And to make the Hollywood world even smaller and weirder, you should know that Gwyneth Paltrow introduced the pair, since she was dating Ben Affleck at the time and he and Matt Damon have been buds for years. (Then Paltrow and Ryder had a falling out, but that's a different story). Anyway, after their meet-cute in December 1997, Damon and Ryder dated for three years until calling quits in 2000, and Damon moved on to Penelope Cruz.

Their relationship has been pretty well-documented since, after meeting on the set of Days of Thunder in 1990, they were married for 11 years. They adopted two children together, Isabella and Connor, and starred together again in Eyes Wide Shut. Kidman has since made a life with country singer Keith Urban, and, well, Cruise has certainly had his share of marital drama with Katie Holmes since.

They're the '90s couple that could! Back in their leather-clad, frosted tips days, they were Posh and Becks, and Miss Victoria Adams was best known for her alter-ego, Posh Spice. Beckham was a rising star on the English football scene. They met in 1997 and more than two decades, a cross-Atlantic move, three strapping sons, and one adorable daughter later, they're still going strong.

"From the moment I saw him, I realized he was the most incredible person I'd ever been so fortunate to meet," Barrymore gushed to People after she and Wilson started dating in 1996. The couple split in 1999, shortly after filming Home Fries. Random fun fact of the day: Barrymore is godmother to Frances Bean Cobain, the daughter of Courtney Love and Kurt Cobain.