17 Photos Of '90s Couples Whose Breakups Broke Our Hearts Into Tiny Pieces

2015 seemed to be the year of the devastating celebrity breakup, from Emma Stone and Andrew Garfield to Blake Shelton and Miranda Lambert. And while the year certainly boasted its fair share of star splits (still mourning Ben Affleck and Jennifer Garner, TBH), it was nothing compared to the slaughter that the '90s took upon Hollywood's fave celeb couples. I mean, R.I.P. to the fairytale Reese Witherspoon and Ryan Phillippe romances of the world — those '90s celeb breakups took no prisoners.

And, oh, what a tangled web the these A-list celeb couples weaved. In the set of photos below alone, there are a surprising number of Hollywood couples whose romances overlapped with one another. Like the fact that Gwyneth Paltrow was engaged to Brad Pitt, who later married Jennifer Aniston. Or how Paltrow dated Ben Affleck, who went on to be engaged to Jennifer Lopez, who famously dated P. Diddy (then known as Puff Daddy) in the late '90s. Call it Hollywoodcest, call it fate, call it whatever. It's kinda random that these stars and their relationships are all interconnected in some way. Or maybe that's just the entertainment industry for ya.

Re-live some of the best '90s romances below. You know what they say: A picture speaks a thousand words.

Johnny Depp & Winona Ryder

1. Smokin' Hot

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Johnny Depp and Winona Ryder became engaged after co-starring in Edward Scissorhands in 1990.

2. A Look Of Love

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The off-beat actors were engaged for three years before ending their engagement. It was during this time that Depp tattooed "Winona Forever" on his arm — always a wise decision.

3. Heartache

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"I had just done Dracula and Edward Scissorhands. I had just had my first real break-up, the first heartbreak," Ryder told Elle in 2009 of her split from Depp. "And I think it was really ironic because, like, everybody else just thought I had everything in the world, you know, I had no reason to be depressed, everything was sort of at its peak, but inside I was completely lost."

4. Happier Times

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After the two called it quits, Depp had his "Winona Forever" tattoo changed to "Wino Forever." Classic.

Reese Witherspoon & Ryan Phillippe

5. Young Love

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Ryan Phillippe and Reese Witherspoon were EVERYTHING in the '90s. The unfairly good-looking couple got together soon before shooting Cruel Intentions when Witherspoon was just 21 and Phillippe was 22.

6. Cruel Intentions? Not So Much

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Their real-life relationship certainly didn't echo any of their movie title's sentiments: the couple was married for seven years before divorcing in 2007, no cruel intentions involved.

7. Ya Gotta Laugh

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Witherspoon and Phillippe may no longer be married (and both have each remarried to other people), but they have maintained a strong co-parenting relationship for the sake of their children, Ava, 16, and Deacon, 11.

8. Cruel Intentions For Life

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In fact, the pair recently took a stroll through Central Park with their kids and reminisced about how they filmed many of the film's scenes there.

"We got to meet up as a family and took a walk through Central Park with the kids, and it was funny," Phillippe told HuffPost Live . "We were reminiscing then because we shot a lot of Cruel Intentions [there], so there we were with Ava and Deacon talking, and they were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds."

Jennifer Lopez & P. Diddy

9. The '90s Fashion Was Legit

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The only tell-tale sign that this photo was taken in the late '90s is the fashion. From J. Lo's rhinestone-studded bandanna headband to Diddy's see-through shades, the couple's style just screams "1999." Their faces, though, have stayed exactly the same — even more than 15 years later.

10. Who Can Forget About That Dress?

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Lopez's plunging, jungle green Versace gown — which she wore to the 2000 Grammy Awards — literally inspired the guys at Google to create Google Images.

11. But It Wouldn't Last

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Unfortunately, not even a dress like that could keep the couple together, and they broke up in 2001. Fortunately for all of us, the two later danced it up at the 2015 AMAs after-party and the world partied like it was 1999.

Jennifer Aniston & Brad Pitt

12. The Golden Couple

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When Jennifer Aniston and Brad Pitt married in 2000, they were the Hollywood golden couple — and not just because they both shared the same enviable fair-haired locks. Aniston was flying high in TV stardom (Rachel Green is iconic), while Pitt was busy perfecting his heartthrob movie star status.

13. They Perfectly Encapsulated That Early '00s Red Carpet Look

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For the five years they were married, Pitt and Aniston shared a seemingly blissful relationship in the public eye — that is, of course, until Pitt filmed Mr. and Mrs. Smith alongside Angelina Jolie.

14. Trouble In Paradise

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Pitt and Aniston divorced in 2005, and thus began the world's obsession with #Brangelina, which may or may not have started blossoming while Pitt was still married to Aniston. But all's well that ends well: Pitt is now married Angelina Jolie, while Aniston is married Justin Theroux.

Ben Affleck & Gwyneth Paltrow

15. Kissy, Kissy

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Affleck and Paltrow began dating in 1997 after Paltrow ended her engagement with Brad Pitt. (I'd have done the reverse, TBH.)

16. Huggy, Huggy

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After dating on off for three years, the two took their partnership to the big screen and starred in the 2000 film Bounce together. (I don't remember it, either.)

17. And The Inevitable Splitty, Splitty

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After dating on and off for three years, Paltrow ended things with Affleck and later told Howard Stern that the actor "was not in a good place in his life to have a girlfriend." This was, of course, after saying that he would have been better off "dating a Scores stripper." Yikes.

R.I.P. to all of our fave '90s couples. May your romance live on through Getty Images.