From Jennifer Aniston to Christina Applegate, Every Red Carpet Date Brad Pitt Has Ever Had

Brad Pitt & Shalane McCall (1988)

The Dallas costars attended a red carpet event together in some very ’80s outfits. 

Brad Pitt & Jill Schoelen (1988)

The couple, who would get engaged the following year, dressed to impress for the Hurlyburly opening night party…whatever that is. 

Brad Pitt & Christina Applegate (1989)

Applegate famously ditched Pitt for another guy at the 1989 MTV Video Music Awards. Imagine that.

Brad Pitt & Juliette Lewis (1992)

Aw, Pitt and Lewis (who dated for three years) got all dressed up for his first Oscars. 

Brad Pitt &  Jitka Pohlodek (1994)

Pitt channeled Kurt Cobain at the Legends of the Fall premiere with Pohlodek at his side. 

Brad Pitt & Gwyneth Paltrow (1996)

And then came Gwyneth. 

Brad Pitt & Gwyneth Paltrow (1997)

After Pitt proposed in 1996, they even got matching haircuts for The Devil’s Own New York premiere. Sadly, they parted ways the following year.

Brad Pitt & Claire Forlani (1998)

The 50th Annual Writers Guild of America Awards called for a night out with his Meet Joe Black costar, whom he briefly dated. 

Brad Pitt & Jennifer Aniston (1999)

Welcome to the era of Brad and Jen. 

Brad Pitt & Jennifer Aniston (2002)

Sunglasses were clearly required at the 59th Annual Golden Globe Awards, and Pitt was happy to oblige. 

Brad Pitt & Jennifer Aniston (2004)

’Twas the golden age of Aniston and Pitt’s marriage, which kicked off in 2000. 

Brad Pitt & Angelina Jolie (2007)

Enter Angelina Jolie at the 64th Annual Golden Globe Awards.

Brad Pitt & His Mom, Jane Pitt (2012)

There’s no better date. 

Brad Pitt & Angelina Jolie (2012)

Brangelina shined bright at the 84th Academy Awards. 

Brad Pitt & Family (2014)

Pitt brought half of his brood (Maddox, Shiloh and Pax) and his parents to the Unbroken premiere. 

Brad Pitt & Angelina Jolie (2015)

The couple, who wed in 2014 and ultimately parted ways in 2016, made their last walk down the red carpet together at the premiere of their film By the Sea.