A Look Back at Brad Pitt’s Oscars Dates Through the Years

One aspect of the Academy Awards red carpet that never gets old is seeing who that year’s A-list stars bring as their dates, from long-time spouses to burgeoning new romances. One particularly of-interest man-about-town is Brad Pitt, who practically owned the Oscars red carpet for years when he and ex-wife Angelina Jolie would walk down it in style. Since their 2016 split, we’ve all been waiting for Pitt to take a new paramour down the red carpet — and who will join the decorated cadre of women to walk on Pitt’s arm on Hollywood’s biggest night.

Pitt’s past dates have been particularly on our mind since Pitt and Jennifer Aniston’s 2020 SAG Awards reunion, which made us seriously nostalgic — and curious if there could be another chance for the power couple. While Pitt and Aniston never actually attended the Academy Awards together, they were a red carpet fixture of the early 2000s — maybe one year, they’ll hit the carpet together again just for old time’s sake?!

The truth is, the Pitt Oscar date is made even rarer by the fact that only a select few women have ever accompanied the Fight Club star to the Oscars — largely because he’s only ever been to the show a handful of times himself. It’s not his fault though. For all of his incredible performances over the years, he’s only been nominated a few times. In 1996, he snagged a Best Supporting Actor nomination for 12 Monkeys, and he’s been nominated as best actor twice; in 2009, for his role in The Curious Case of Benjamin Button, and in 2012 for Moneyball. The A-lister has also been nominated as a producer twice, accepting a gold statue for best picture in 2014 for 12 Years a Slave, and in 2020, he finally accepted an Oscar for best supporting actor in Once Upon a Time in Hollywood.

Let’s take a trip down memory lane and remember all of Brad Pitt’s Oscars dates over the years as we look forward to this weekend’s show.

A version of this story was originally published in 2020.