Our Favorite Celebrity Couples of the ’90s

One common trait most celebrity couples in the 90s share are that their romances, and even their marriages, are often fleeting. Still, several celebrities achieved a romantic synergy in the public eye during the 1990s, garnering them the fame that they likely couldn’t have accomplished alone.

Here are our favorite celebrity couples of the 90s.

20.) Britney Spears and Justin Timberlake

britney spears and justin timberlake

New Idea

  • Dated for 3 years

The two music icons started dating in the late 1990s. Their most iconic appearance was when they wore matching denim on the red carpet. Spears and Timberlake met during the Mickey Mouse Club years.

Even though they met when they were much younger, they started dating in 1998.

19.) Sarah Jessica Parker and Robert Downey Jr.

sarah jessica parker and robert downey jr

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  • Dated for 7 years

This 90s celebrity couple started dating from the mid-1980s to the early 1990s, they are still considered our favorite. During their time on the set of Firstborn, the two started dating.

When they were a couple, Downey struggled with drug addiction. Parker said she spent a lot of time worrying about him.

18.) Reese Witherspoon and Ryan Phillippe

reese witherspoon and ryan phillippe

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  • Dated for 2 years
  • Married for 8 years (Divorced)

This iconic celebrity duo fell in love on the set of Cruel Intentions.

They only dated for two years before getting married. Before divorcing in 2006, Witherspoon and Phillippe had two children together.

17.) David and Victoria Beckham

David and Victoria Beckham

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  • Dated for 2 years
  • Married for 20 years (Still Married)

There are one of the last few couples that are still together after the 1990s ended. They met at a charity soccer match in 1997. A year later, they announced their engagement and tied the knot in 1999.

Today, they are still the most photographed and influential couples.

16.) Will and Jada Pinkett Smith

will and jada pinkett smith

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  • Dated for 2 years
  • Married for 22 years (Still Married)

The Smiths are another celebrity couple in the 90s that survived. They first met on the set of the Fresh Prince of Bel-Air in 1994. They started dating in 1995, got married in 1997, and the rest is history.

Two children later, the couple is still together and thriving.

15.) Ellen DeGeneres and Anne Heche

ellen degeneres and anne heche

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  • Dated for 3 years

After Ellen came out in 1997, the comedian and the actress Anne Heche went public with their relationship.

They were known for always matching each other on the red carpet.

14.) Kurt Cobain and Courtney Love

Kurt Cobain and Courtney Love

Terry McGinnis/WireImage

  • Dated for 2 years
  • Married for 2 years

In the early 1990s, Love and Cobain were the king and queen of alternative music.

In 1992, they had their first child together. Unfortunately, in 1994, Cobain died of suicide.

13.) Sarah Jessica Parker and Matthew Broderick

sarah jessica parker and matthew broderick

ET Online/Getty Images

  • Dated for 6 years
  • Married for 22 years (Still Married)

Even though the two started dating in the late 1990s, they are the rare celebrity couple that is still together!

They have been through some ups and downs, but they were able to keep a strong connection.

12.) Jennifer Love Hewitt and Carson Daly

jennifer love hewitt and carson daly

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  • Dated for 1 year

Jennifer Love Hewitt and Carson Daly had amazing careers during the 90s.

They connected for a short time and then broke up after a year together.

11.) Cindy Crawford and Richard Gere

cindy crawford and richard gere

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  • Married for 4 years (Divorced)

The model and the actor married in the 1990s.

Their marriage only lasted four years before they divorced.

10.) Johnny Depp and Winona Ryder

Johnny Depp and Winona Ryder

Barry King/WireImage

  • Dated for 5 years

Johnny Depp met Winona Ryder on the set of Edward Scissorhands in the late 80s. Things went fast, and the two ended up engaged in 1990.

Even though they thought it was love at first sight, the two ended up breaking up in 1993.

9.) Faith Hill and Tim McGraw

faith hill and tim mcgraw

Jason Simanek

  • Married for 20 years (Divorced)

Known as one of the most famous country couples in the world, the two started dating in the 1990s.

Everyone thought they were a success story, but in 2016, the singers ended their marriage after 20 years together.

8.) Gwyneth Paltrow and Ben Affleck

gwyneth paltrow and ben affleck

Reuters

  • Dated for 3 years

The actor and actress had a roller-coaster relationship that started in the late 1990s.

Thankfully, it ended in 2000 before anything could get too messy.

7.) Matt Damon and Minnier Driver

matt damon and minnier driver

Rex

  • Dated for 1 year

The two met on the set of Good Will Hunting. Damon and Driver started dating in 1996.

It did not last long. After only a year of dating, they broke up.

6.) Courtney Cox and Michael Keaton

courtney cox and michael keaton

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  • Dated for 6 years

Courtney Cox was in a high profile relationship with Michael Keaton. They dated over six years before breaking things off in 1995.

Cox said it was the most important relationship she was ever involved in.

5.) Sandra Bullock and Matthew McConaughey

sandra bullock and matthew mcconaughey

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  • Dated for 4 years

Two more celebs that have gone on to bigger and better things since their relationship are Sandra Bullock and Matthew McConaughey. The two met on the set of the 1996 film A Time to Kill and dated till the end of the decade.

What makes this 90s couple unique is their ability to remain friends for a long time after the breakup.

4.) Bruce Willis and Demi Moore

bruce willis and demi moore

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  • Married for 13 years (Divorced)

While their relationship extended a bit beyond the 1990s, Bruce Willis and Demi Moore certainly hit their stride during the decade. The pair married from 1987 to 2000, and they have three children together.

Both accomplished some of their best film work during the decade.

3.) Jennifer Lopez and Sean “Diddy” Combs

jennifer lopez and sean diddy combs

KMazur/Wireimage

  • Dated for 2 years

You could argue that no 1990s celebrity couple boosted their statures through their companionship than J Lo and Diddy. The two dated from 1997 to 1999.

Lopez used her celebrity boost to transition from fledgling actress to film, TV and music mogul. Puff Daddy changed his name a few times and remained a prominent music entertainer and producer for years.

2.) Brad Pitt and Gwyneth Paltrow

brad pitt and gwyneth paltrow

Rex

  • Dated for 3 years

While this wasn’t the most famous celebrity couple for either actor, Brad Pitt and Gwyneth Paltrow were together for a few years in the mid-1990s.

A September 2011 Business Insider article noted the lack of Internet evolution at the time as to why this power couple didn’t achieve the same stature as Braniston or “Brangelina.”

1.) Tom Cruise and Nicole Kidman

tom cruise and nicole kidman

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  • Married for 11 years (Divorced)

Without a doubt, no celebrity couple in the 1990s had greater collective star power than Tom Cruise and Nicole Kidman. The two met on the Days of Thunder movie set in 1990 and stayed together for ten years or the entire decade of the 90s.

In the end, Cruise’s dedication to Scientology and disagreements over parenting were reportedly among contributing factors to the couple’s ultimate demise.

 

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