He is best known for his roles in Bringing Out the Dead (1999), Dogma (1999), Jersey Girl (2004), Gone Baby Gone (2007), It's Kind of a Funny Story (2010), Grand Theft Auto V (2013) Captain Marvel (2019), Funny Pages (2022), Air (2023), and Our Flag Means Death (2022–2023).

Theater credits include Red-Handed Otter at Cherry Lane Theater, Uncle Vanya at Soho Repertory Theatre, Golden Child by David Henry Hwang at Signature Theatre Company, and Tales From My Parents Divorce by The Civilians.

[3] He has appeared occasionally in feature films, including Bringing Out the Dead (1999),[3] Dogma (1999), Vulgar (2000),[3] The Third Wheel (2002), Jersey Girl (2004), Gone Baby Gone (2007),[3] The Killer Inside Me, I'm Still Here and It's Kind of a Funny Story (2010),[3] Captain Marvel (2019), Funny Pages (2022), and Air (2023).

[4] In 2016, he starred in the Annie Baker play The Flick which debuted Off-Broadway at Playwrights Horizons in 2013,[5] and went on to win the 2014 Pulitzer Prize.

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