Minnie Driver & Matt Damon
The Good Will Hunting co-stars had a very public breakup back in 1998.
Matt Damon & Winona Ryder
The talented twosome dated briefly in the late-nineties but ultimately called it quits in 2000.
Michael Keaton & Courteney Cox
The Beetlejuice actor and Friends star dated from 1989 to 1995.
David Arquette & Alyssa Milano
The Charmed actress and Scream star dated in 1991.
Kiefer Sutherland & Julia Roberts
The actors began dating in 1990 after co-starring in Flatliners. They announced their engagement in August and planned to marry on June 14, 1991. However, Roberts called off her wedding to Sutherland three days before it was scheduled to take place.
Matthew Perry & Julia Roberts
The pair dated briefly in 1996 following Roberts' guest appearance on Friends.
Benjamin Bratt & Julia Roberts
The pair dated from 1998 to 2001.
Whoopi Goldberg & Ted Danson
After meeting on the set of Made in America in 1993, Goldberg and Danson dated briefly. During a 2015 appearance on Bravo's Watch What Happens Live!, the View co-host joked she'd "bone so many people" since dating Danson.
Halle Berry & Danny Wood
The future Oscar winner briefly dated the New Kids on the Block singer in 1990.
Madonna & Dennis Rodman
The singer-actress briefly dated the former NBA star in 1994.
Madonna & Vanilla Ice
The unlikely duo dated for about eight months in 1991.
Christine Taylor & Neil Patrick Harris
The HIMYM star dated the actress (and future wife of Ben Stiller) in 1997. "She's the coolest, nicest chick ever. She's an absolute catch," Harris, who is married to David Burtka, later revealed in an interview with Howard Stern. "And I thought, 'If I'm not going to feel the super sparks with her... it probably means I'm gay."
Cameron Diaz & Matt Dillon
The Something About Mary co-stars dated from 1995 to 1998.
Ashton Kutcher & January Jones
The Two and a Half Men star and Mad Men actress dated from 1998 to 2001.
Anne Heche & Ellen DeGeneres
The former pair dated from 1997 to 2000.
Richard Gere & Cindy Crawford
The actor and supermodel were married from 1991 to 1995.
Carmen Electra & Dennis Rodman
The model-actress and NBA player were married briefly in 1998.