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As a playwright, Letts is known for having written for the Steppenwolf Theatre, Off-Broadway and Broadway theatre. His works include Killer Joe, Bug, Man from Nebraska, August: Osage County, Superior Donuts, Linda Vista, and The Minutes. Letts adapted three of his plays into films, Bug and Killer Joe, both directed by William Friedkin, and August: Osage County, directed by John Wells. His 2009 play Superior Donuts was adapted into a television series of the same name. As a stage actor, Letts has performed in various classic plays with the Steppenwolf Theatre since 1988. He made his acting Broadway debut as George in the revival of Edward Albee's play Who's Afraid of Virginia Woolf?, which earned him a Tony Award for Best Actor in a Play. He continued acting on the Broadway stage in The Realistic Joneses, All My Sons, and The Minutes.

On television, he is known for his portrayal of Andrew Lockhart in seasons 3 and 4 of Showtime's Homeland from 2013 to 2014, and pyramid-scheme con-artist Nick on the HBO comedy series Divorce from 2016 to 2019. He played Jack McKinney in the HBO sports drama series Winning Time: The Rise of the Lakers Dynasty (2022–2023) for which he was nominated for the Primetime Emmy Award for Outstanding Guest Actor in a Drama Series. On film he has portrayed Henry Ford II in James Mangold's sports drama Ford v Ferrari (2019) and Herb Sargent in Jason Reitman's biographical comedy-drama Saturday Night (2024). He has also taken leading roles in The Lovers (2017) as well as supporting roles in The Big Short (2015), Indignation (2016), Imperium (2016), Lady Bird (2017), The Post (2017), Little Women (2019), and A House of Dynamite (2025).