THROWBACK THURSDAY

A Photographic Guide To Everyone Brad Pitt Has Dated

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Brad Pitt leaning on a car
Photograph by Juergen Teller; Creative Partner to Juergen Teller: Dovile Drizyte; Styled by Sara Moonves. Skin by Stacey Panepinto; Hair by Malcolm Edwards at LGA Management; Manicure by Michelle Saunders.

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. Since the split, Pitt’s name has tumbled around the dating rumor mill quite a bit (and it didn’t exactly help when the actor was discovered flirting with real people under his real name, William, a couple years later). Allegedly, the actor has also been approached by a number of his famous exes, including Kate Hudson, Juliette Lewis, Christina Applegate, and Gwyneth Paltrow, as well as allegedly flirting with Sienna Miller. There were even rumors that Pitt dated MIT professor Neri Oxman (they didn’t) and actress Alia Shawkat (also untrue, though they did share a meal at In-N-Out Burger after seeing Thundercat perform in L.A.). The latest in the rumor mill? Oscar-nominated musician and actress Andra Day, who set the record straight and told the press she has never met the man. 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. Take a walk down celebrity couple memory lane, here.

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Where it all began: Brad Pitt and then-girlfriend Robin Givens in Los Angeles. The couple were together from 1986-1987.

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Actress Shalane 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.

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McCall and Pitt are again spotted in Beverly Hills. The couple dated in 1987.

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On-set co-stars, Brad Pitt and Jill Schoelen enjoyed a brief relationship that drew great media attention, from 1988-1989.

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Brad Pitt and Jill Schoelen, who dated for one year, are spotted by paparazzi. The couple were together from 1988-1989.

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Brad Pitt and Jill Schoelen attend the Hurlyburly play performance on January 15, 1989 at Westwood Playhouse in Westwood, California.

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Brad Pitt and Jill Schoelen at the 20/20 Club in Los Angeles.

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Pitt and Schoelen at the 8th Annual Jimmy Stewart Marathon Kick-Off Party.

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Brad Pitt and Christina Applegate during 1989 MTV Video Music Awards in Los Angeles, California. The couple were together in 1989.

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Christina Applegate and Brad Pitt spotted again in 1989.

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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.

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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.

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Lewis and Pitt arrived together at the 7th Annual IFP/West Independent Spirit Awards in 1992.

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Lewis and Pitt arrived together at the 64th Annual Academy Awards in 1992.

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Juliette Lewis and Brad Pitt attend the Johnny Sude Beverly Hills Premiere on August 19, 1992.

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Brad Pitt and Juliette Lewis during The Last of the Mohicans Los Angeles Premiere in September 1992.

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Brad Pitt and Juliette Lewis attend the A River Runs Through It premiere in October 1992.

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Brad Pitt and Juliette Lewis attend the 1993 NATO/ShoWest Convention on March 8, 1993 at Bally's Hotel and Casino in Las Vegas, Nevada. The couple were together from 1989 to 1993.

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Brad Pitt and Gwyneth Paltrow attend the Legends Of The Fall U.K. premiere after party in London, 1995. The couple were together from 1994 to 1997.

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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.

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Brad Pitt and Gwyneth Paltrow attend the Living in Oblivion L.A. premiere in 1995.

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Gwyneth Paltrow and Brad Pitt, 1996. The couple were together from 1994-1997.

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Brad Pitt and Gwyneth Paltrow on set of The Devil’s Own (and carrying a copy of W magazine) in 1996.

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Pitt and Paltrow attend The Pallbearer premiere in New York on April 28, 1996.

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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.

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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.

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Brad Pitt and Gwyneth Paltrow in Paris on March 27, 1997.

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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.

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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.

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Aniston and Pitt arrive together at the American Film Institute tribute to Harrison Ford, who received the Life Achievement award from the organization 17 February, 2000 in Beverly Hills.

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The couple attended the Erin Brokovich premiere on March 4, 2000.

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Brad and Jennifer attend the Rock Star premiere in 2001 in Hollywood. The couple were together from 1998-2005.

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Actress Jennifer Aniston and actor Brad Pitt attend The Mexican Westwood premiere in 2001. The couple were together from 1998-2005.

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Brad Pitt and Jennifer Aniston arriving at the premiere of The Good Girl in 2002.

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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.

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Brad Pitt and Angelina Jolie during 64th Annual Golden Globe Awards in 2007, shortly after meeting on the set of Mr. & Mrs. Smith.

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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.

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Brad Pitt and Angelina Jolie at an event in London in June 2014. The couple were together from 2005-2016.

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Brad Pitt and Angelina Jolie attending the premiere of Maleficent at Kensington Palace, London in 2014.

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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.