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Schreiber's early film roles include Mixed Nuts (1994), Party Girl (1995), The Daytrippers (1996), and Big Night (1996). He appeared in the first three Scream horror films (1996–2000), Ransom (1996), The Hurricane (1999), Hamlet (2000), Kate & Leopold (2001), The Manchurian Candidate (2004), The Painted Veil (2006), X-Men Origins: Wolverine (2009), Pawn Sacrifice (2014), and Spotlight (2015). He acted in the Wes Anderson films Isle of Dogs (2018), The French Dispatch (2021), and Asteroid City (2023). He made his directorial film debut with Everything Is Illuminated (2005).

He made his Broadway debut in In the Summer House (1992). He earned the Tony Award for Best Featured Actor in a Play for playing Richard Roma in the David Mamet play Glengarry Glen Ross (2005). He was Tony-nominated for his roles in the Eric Bogosian play Talk Radio (2007), the Arthur Miller revival A View from the Bridge (2010) and the John Patrick Shanley revival Doubt (2024). He also acted in Les Liaisons Dangereuses (2016).

For his television roles, he most notably portrayed the titular character in the Showtime drama series Ray Donovan (2013–2020). He reprised the role in the television film Ray Donovan: The Movie (2022). The role has earned him nominations for three Primetime Emmy Awards and four Golden Globe Awards. He also portrayed Orson Welles in the HBO film RKO 281 (1999) and Otto Frank in the Nat Geo miniseries A Small Light (2023).