14 Iconic Celebrity Couples We Loved in the '90s.

Ah, the 90s. This time before Y2K was unforgettable for many and also marked the beginning of a time when the public began to have more access to the lives of celebrities through television and paparazzi photos. Whether you’re celeb obsessed or not, you have to admit that these famous 1990s couples were absolute #relationshipgoals at the time.

1. Kate Moss and Johnny Depp

This edgy couple was the epitome of cool, although people who now know about the Depp and Heard affair may feel differently about it. Johnny and Kate dated for about four years, but the two broke up due to the actor’s mood swings. Yes, it follows!

2. Brad Pitt and Gwyneth Paltrow

Today, Paltrow is happily married to another Brad, who often collaborates with Ryan Murphy on TV shows. But in her 20s, she had a thing for Brad Pitt, whom she met on the set of “Se7en.” Although he proposed, they broke up just six months later.

3. Tom Cruise and Nicole Kidman

Today, Nicole Kidman has an everlasting love story with Keith Urban, but before there was Keith, there was Tom. Married in the 1990s, the two were together until 2001, when their relationship mysteriously ended. We’d say she dodged a bullet with this whole Scientology thing!

4. Britney Spears and Justin Timberlake

The 90s were the peak of Britney’s era, and no one knew that better than JT, who ended up falling for her. They started dating around 1998 when they went on tour together, and the song “Cry Me A River” he wrote in the early 2000s is about Britney Spears.

5. Pam Anderson and Tommy Lee

Blonde bombshell Pam Anderson and Motley Crue drummer Tommy Lee have had a rollercoaster love story. Married for three straight years, the Los Angeles couple had two children before eventually divorcing, but they stayed on and off for several years.

6. Whitney Houston and Bobby Brown

This love story lasted 14 years but ended tragically with both substance abuse and domestic violence. Houston initially rejected Brown’s marriage proposal because she did not want to get married at the time. But in 1992, the two married and the ensuing relationship ended a decade later.

7. Drew Barrymore and Luke Wilson

Quirky redhead Drew Barrymore has been Hollywood’s darling for decades, and beau Luke Wilson began a romantic relationship with her after they filmed the 1997 movie Home Fries. After dating for a few years, they broke up before filming Angels of Charlie’, but they still had to work together—awkward!

8. Kurt Cobain and Courtney Love

This rocker couple had a controversial relationship in the media and public eye, especially since Love was still using banned substances when she was pregnant. In 1994, the romance ended abruptly when Kurt took his own life, but they are still known as the ultimate grunge romance.

9. Bruce Willis and Demi Moore

Once a ’90s power couple, Bruce Willis and Demi Moore remained married until 2000. At that point, they had three children, but remained on good terms after the divorce. Willis even attended Demi and Ashton’s wedding in 2005.

10. Winona Ryder and Matt Damon

After spending two years in a relationship, Ryder and Damon went through a public breakup. The two were apparently introduced by Gwyneth Paltrow, who at the time was dating Damon’s BFF, Ben Affleck.

11. Cameron Diaz and Matt Dillon

Before Cameron later found love with Benji Madden, her romance with Matt Dillon was unforgettable. According to Matt Cameron, she was his muse and the first “deep emotional connection” he was in at the time. They weren’t into drama or the limelight and kept their relationship pretty low-key.

12. Ethan Hawke and Uma Thurman

Based on Uma’s interview with Oprah, her and Ethan’s breakup was difficult for the entire family. Married in 1998 and divorced in 2005, the two share two children: Maya and Levon. Thurman was quoted as saying that she needed to take responsibility for the failure of her marriage.

13. Hugh Grant and Elizabeth Hurley

Apparently, exes really can stay friends, and Grant and Hurley are a great example of that. After a 13-year relationship that began in 1987, they finally separated in 2000. However, they remained best friends and often talk about each other in interviews. Grant said she is “the number one person I call in a crisis.”

14. Brooke Shields and Andre Agassi

When stunning actress Brooke Shields married tennis megastar Andre Agassi, everyone thought the power couple would last forever. Just a few years later, however, it all ended in an ugly divorce. In his memoir, Shields revealed that Andre had been accused of substance abuse, and when he saw her flirting in a guest appearance on Friends, he smashed all of his tennis trophies.

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