In film, he has appeared in Hedwig and the Angry Inch (2001), Bully (2001), Murder by Numbers (2002), The Dreamers (2003), Last Days (2005), Silk (2007), Funny Games (2007), I Origins (2014), and Ghost in the Shell (2017).

"[6] He has also stressed that he chooses roles not with the hope that they will garner commercial success or to gain notoriety but to create art, challenge the audience, and ultimately contribute to a project that he is proud of: To be honest, I make very controversial films.

[7]In 2004, Pitt has also appeared in The Heart Is Deceitful Above All Things and The Village and in 2005 starred in Last Days as a rock musician "inspired" by Nirvana frontman, Kurt Cobain.

On the set of Last Days, he met Thurston Moore of Sonic Youth, who had been hired by Van Sant to serve as the film's music consultant.

In 2006, he starred in the unconventional romantic comedy Delirious as a young homeless man who befriends a celebrity photographer and falls in love with a pop singer.

The following year, he played opposite Keira Knightley in Silk, adapted from the novel by Alessandro Baricco, as Hervé Joncour, a French silkworm smuggler, who falls in love with a baron's concubine while in Japan.

[5] During his theater debut, a casting agent whom Pitt had mistaken for a police officer attempting to arrest him noticed him and recommended him for a role on the television series Dawson's Creek.

In 2010, Pitt was cast as Jimmy Darmody in the HBO series Boardwalk Empire (about the rise of Atlantic City during the Prohibition era), as the protégé of corrupt politician Nucky Thompson.

[13] In January 2015, Pitt made his official directorial debut with a campaign film for fashion label Rag & Bone's Spring 2015 collection.

The video features Pitt and prior co-stars actress Astrid Bergès-Frisbey—the new face of Rag & Bone womenswear—and British actor Stephen Graham, from I Origins and Boardwalk Empire, respectively.

Says Rag & Bone co-head, Marcus Wainwright, "[Pitt]'s a really talented actor and musician, and he came to us with this concept of doing a film-based campaign.

[19][20] In July 2022, Pitt was arrested and charged with assault and petty larceny after allegedly hitting another man multiple times and taking his phone.