Brad Pitt and Robin Givens, 1988. (Photo: Archive)
Heath Ledger and Heather Graham, 2000 to 2001. (Photo: Archive)
George Clooney and Renee Zellweger, 2001. (Photo: Archive)
Winona Ryder and Jimmy Fallon, 2002. (Photo: Archive)
Cameron Diaz and Matt Dillon, 1995 to 1998. (Photo: Archive)
Ryan Gosling and Sandra Bullock, 2002. (Photo: Archive)
Winona Ryder and Matt Damon, 1997 to 2000. (Photo: Archive)
Cher and Tom Cruise, 1980s. (Photo: Archive)
Courteney Cox and Michael Keaton, 1989 to 1995. (Photo: Archive)
Moby and Natalie Portman, 2001. (Photo: Archive)
Justin Timberlake and Fergie, 1996. (Photo: Archive)
Jennifer Grey and Matthew Broderick, 1987 to 1988. (Photo: Archive)
Johnny Depp and Ellen Barkin, 1994. (Photo: Archive)
Britney Spears and Colin Farrell, 2003. (Photo: Archive)
Leonardo DiCaprio and Naomi Campbell, 1995. (Photo: Archive)
Drew Barrymore and Luke Wilson, 1996 to 1999. (Photo: Archive)
Johnny Lee Miller and Angelina Jolie, 1996 to 1999. (Photo: Archive)
Jennifer Aniston and Vince Vaughn, 2005 to 2006. (Photo: Archive)
Macauley Culkin and Mila Kunis, 2002 to 2011. (Photo: Archive)
Some of the couples on this list will surprise you, but be assured: it actually happened! Tom Cruise actually dated Cher. On the other hand, Winona Ryder was absolutely crushing it about 15 years ago.
