After his breakout performance in Steppenwolf Theatre Company’s outreach staging of Arthur Miller’s A View from the Bridge, Brown began working in television and film. He appeared in films such as Backdraft, The Babe, Excessive Force, and Rookie of the Year. In 1993, he moved to Los Angeles and was cast in Wes Craven’s New Nightmare. He also had a minor role in Craven’s Vampire in Brooklyn, and a bigger one as a news cameraman working for Gale Weathers in Craven’s Scream.
He played Warren in the 1998 comedy film There’s Something About Mary and later took roles in Being John Malkovich, Vanilla Sky, Dancing at the Blue Iguana, The Alamo, and The Big White.
In 2009, Brown wrote, produced, and appeared in the film Bloodworth. His 2010s film credits include The Master, The Sessions, The Lone Ranger, Brother’s Keeper, and Wild.
On television, he is best known for his portrayal of Dan Dority on the HBO series Deadwood (2004–2006). He has also guest starred on Bates Motel, Rectify, Luck, American Horror Story, Justified, Six Feet Under, NYPD Blue, X-Files, The Mentalist, CSI: Crime Scene Investigation, Ellen, Seinfeld, True Detective, and others. He also portrayed singer Meat Loaf in VH1’s television film Meat Loaf: To Hell and Back. In 2013, he performed the voice and motion capture of Bill in the critically acclaimed video game The Last of Us.
Most recently, Brown has appeared in The Mandalorian and as the lead in the hit CBS series Sheriff Country.
Brown also writes and performs with the country music band Sacred Cowboys.