21 Iconic Exes from Years Past

They may not be together anymore, but we'll always remember these celebrity couples. For more ex drama, catch You, Me & my Ex every Monday at 9/8c!

By: Jessica Butler

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Brad Pitt and Jennifer Aniston

These two ended their five-year marriage in 2005.

Ben Affleck and Jennifer Lopez

"Bennifer" made plans to tie the knot, but they called it quits in 2004. Although the pair decided to get hitched nearly two decades later in 2022, we couldn't help but include these former exes.

Lisa Marie Presley and Michael Jackson

These two ended their nearly two-year marriage in 1996.

Bruce Willis and Demi Moore

The actors filed for divorce in 2000 after 11 years of marriage.

Ryan Phillippe and Reese Witherspoon

After seven years of marriage, the "Cruel Intentions" co-stars divorced in 2006.

Lisa Bonet and Lenny Kravitz

The couple spent six years together before divorcing in 1993.

Katie Holmes and Tom Cruise

The power couple split in 2012, ending their six-year marriage.

Sarah Jessica Parker and Robert Downey Jr.

After seven years together, the couple ended things in 1991.

Vanessa Hudgens and Zac Efron

The "High School Musical" co-stars ended their five-year relationship in 2010.

Courteney Cox and David Arquette

The actors' divorce was finalized in 2013, closing the door on their 11-year marriage.

Heidi Klum and Seal

The model and singer officially divorced in 2014 after seven years of marriage.

Mariah Carey and Nick Cannon

These two were married for six years, split up in 2014, reunited briefly, and officially divorced in 2016.

Helena Bonham-Carter and Tim Burton

Their 13-year marriage came to an end in 2014.

Antonio Banderas and Melanie Griffith

After 18 years of marriage, the actors split up in 2015.

Emma Stone and Andrew Garfield

"The Amazing Spider-Man" actors dated from 2011 to 2015.

Kourtney Kardashian and Scott Disick

After meeting in 2006, the couple dated for two years and broke up — only to reconcile again and again and officially end things in 2015.

Cassie Ventura and Sean "Diddy" Combs

The musicians dated on and off for a decade and called it quits in 2018.

Selena Gomez and Justin Bieber

The singers had an on-and-off relationship from 2011 to 2018.

Channing Tatum and Jenna Dewan

After nine years of marriage, the "Step Up" co-stars called it quits in 2018.

Pete Davidson and Ariana Grande

These two began dating in 2018 and got engaged after two months. The couple split later that year, ending their 5-month relationship.

Liam Hemsworth and Miley Cyrus

"The Last Song" co-stars dated on and off for 10 years and separated after less than a year of marriage in 2019. Their divorce was finalized in 2020.

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