In August 2006, Heslov and George Clooney started Smokehouse Pictures and began writing screenplays for production. He was nominated for an Academy Award for Best Original Screenplay (with Clooney) and as Producer for Best Film for Good Night, and Good Luck. Heslov also appears in the film as Don Hewitt, the Director of the TV series See It Now, around which the movie is centered. He directed a screen adaptation of The Men Who Stare at Goats, starring Clooney, Ewan McGregor, Jeff Bridges, and Kevin Spacey and co-produced The American starring Clooney in 2012. He also worked on 2011's The Ides of March. In June 2012, he was invited to join the Academy of Motion Picture Arts and Sciences.