Clapp was born in North Conway, New Hampshire. He graduated from Williams College in 1971. At Williams College, he met frequent collaborators David Strathairn and John Sayles. Clapp also studied at The National Theater Institute at the Eugene O'Neill Theater Center (Fall 1970).
Clapp has appeared in numerous TV shows such as Check it Out! and Night Court as well as numerous stage plays. His film credits include Return of the Secaucus 7 (1979), Running (1979), Matewan (1987), Eight Men Out (1988, as Chicago White Sox catcher Ray Schalk), Termini Station (1989), The Rage: Carrie 2 (1999), Rules of Engagement (2000), Sunshine State (2002), and Flags of Our Fathers (2006) as United States Marine Corps Gen. Holland Smith. He appeared in the Star Trek: Deep Space Nine episode "Vortex."
From 1993 to 2005, Clapp played Detective Greg Medavoy on "NYPD Blue." He won an Emmy for the role.
In 2007, he appeared as Coach Mad Maddox in The Game Plan. On Broadway, he most recently appeared in the revival of David Mamet's Pulitzer Prize-winning play Glengarry Glen Ross, where he was nominated for a Tony Award for Best Performance by a Featured Actor in a Play. He also played Alan Silver in episode Holiday Spirit in Ghost Whisperer (3x10).

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