On September 20, 2016, the entertainment world shattered, as Angelina Jolie filed from divorce from Brad Pitt. It had been twelve years since the couple were first spotted together following their starring roles in
Mr. and Mrs. Smith—the official confirmation came in early 2006 when Jolie announced she was pregnant with Pitt’s child—and just two years after the couple officially tied the knot. Now, six months after the split, it appears that Pitt may be ready to move on. Allegedly, the actor has been approached by a number of his famous exes, including Kate Hudson, Juliette Lewis, Christina Applegate, Thandie Newton, and Gwyneth Paltrow, as well as allegedly flirting with a new blonde: Sienna Miller. While of course all celebrity gossip rumors are to be taken with a grain of salt, the story is valuable if only for the reminder that Pitt has a long history of dating Hollywood’s most eligible bachelorettes. Here, a walk down celebrity couple memory lane.
A pre-divorce Angelina Jolie and Brad Pitt arrive at the premiere of
By The Sea in Hollywood, in November 2015. The couple were together from 2005-2016.
Brad Pitt and Angelina Jolie attend the Global Summit to End Sexual Violence and Conflict in London in June 2014.The couple were together from 2005-2016.
Angelina Jolie and Brad Pitt, who met on the set of
Mr. and Mrs. Smith, arrive for the premiere of The Curious Case of Benjamin Button (2008). The couple were together from 2005-2016.
Where it all began: Brad Pitt and then-girlfriend Robin Givens in Los Angeles. The couple were together from 1986-1987.
Actress Shalene McCall and Brad Pitt enjoyed a brief dalliance after meeting on the set of TV show
Windmills of the Gods. The couple dated in 1987.
McCall and Pitt are again spotted in Beverly Hills. The couple dated in 1987.
Brad Pitt and Jill Schoelen, who dated for one year, are spotted by paparazzi. The couple were together from 1988-1989.
On-set co-stars, Brad Pitt and Jill Schoelen enjoyed a brief relationship that drew great media attention. The couple dated in 1987.
Brad Pitt and Jill Schoelen at the 20/20 Club in Los Angeles. The couple dated in 1987.
Brad Pitt & Christina Applegate during 1989 MTV Video Music Awards in Los Angeles, California. The couple were together from 1988-1989.
Christina Applegate and Brad Pitt spotted again in 1989. The couple were together from 1988-1989.
Brad Pitt and actress Juliette Lewis enjoyed a lengthy long relationship in the public eye. Here they are in 1991. The couple were together from 1989-1993.
Brad Pitt and Juliette Lewis at the AMC Theater in Santa Monica, for the premiere of
Thelma & Louise (1991). The couple were together from 1989-1993.
Brad and Gwyneth Paltrow attend the Hamlet Broadway Play Opening Night Performance in 1995, in New York City. The couple were together from 1994-1997.
Gwyneth Paltrow and Brad Pitt, 1996. The couple were together from 1994-1997.
Brad Pitt and girlfriend actress Gwyneth Paltrow arrive before the 68th Annual Academy Awards on March 25, 1996 in Los Angeles, California. The couple were together from 1994-1997.
Brad Pitt and actress Gwyneth Paltrow attend
The Devil’s Own New York City premiere on March 13, 1997, in New York City. The couple were together from 1994-1997.
Actress Claire Forlani and actor Brad Pitt attend the 50th Annual Writers Guild of America Awards in 1998, in Beverly Hills, California. The couple dated in 1998.
Brad and Jennifer attend the
Rock Star premiere in 2001 in Hollywood. The couple were together from 1998-2005.
Actress Jennifer Aniston and actor Brad Pitt attend
The Mexican Westwood premiere in 2001. The couple were together from 1998-2005.
Brad Pitt and Jennifer Aniston, married for five years, appear here at the 51st Annual Primetime Emmy Awards, in 1999. The couple were together from 1998-2005.
The couple, thought to be an American institution, divorced in 2005. Here the couple make an appearance at the 59th Annual Golden Globe Awards. The couple were together from 1998-2005.