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Shannon began his career as a stage actor in Chicago, where he helped found A Red Orchid Theatre. He has since worked with Steppenwolf Theatre Company, Northlight Theatre, and other groups. Shannon originated the role of Peter Evans in Bug in 2004 and also starred in the 2007 film adaptation with Ashley Judd and Harry Connick, Jr, directed by William Friedkin. His roles in Bug, Killer Joe, and Man From Nebraska were written by Steppenwolf ensemble member Tracy Letts.

Shannon has appeared in several shows in the West End in London, including a production of Woyzeck directed by Sarah Kane.

Shannon made his film debut as a small role in Groundhog Day in 1993 as a wedding groom. Later, he had roles in Jesus' Son, Pearl Harbor, 8 Mile and Vanilla Sky. He played the villain in Kangaroo Jack. After a role in Bad Boys II, he had a major role in Grand Theft Parsons as the hippie, Larry Oster-burg. In 2006, he played the leader of a prison group, Lynard, in Let's go to Prison. Other roles include a gambler in Lucky You and Peter Evans in Bug.

In 2008, Shannon was featured in the off-Broadway production of Stephen Adly Guirgis's The Little Flower of East Orange, presented by LAByrinth Theater Company and The Public Theater, directed by Philip Seymour Hoffman and also featuring Ellen Burstyn.

Married to Steppenwolf ensemble member Kate Arrington with whom he has one daughter.