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He plays Will Pope, Assistant Chief of the LAPD, in the series The Closer.
In an interesting precursor to his joining the Law & Order cast as Skoda, Simmons appeared in Homicide: Life on the Street, portraying a criminal in a Law & Order cross-over episode. in the film Thank You for Smoking (2005) and has been praised for his performance in Juno (2007) as "Mac" Mc Guff, the title character's father.
In 2008, he played a CIA superior in Burn After Reading and appeared in Postal as Candidate Wells. Simmons starred in several films produced or directed by his friend Jason Reitman, including Thank You for Smoking, Juno, Up in the Air and Jennifer's Body. He starred as blind lawyer "Mel Fisher" in Growing Up Fisher.
In the 2014 drama film Whiplash, Simmons played Terence Fletcher, an intensely demanding conductor at the fictional Shaffer Conservatory of Music, who bullies and cajoles his student, Andrew Neiman (Miles Teller).
The wide acclaim for Simmons's performance includes an Academy Award win for Best Supporting Actor.