Howard was born in Independence, Missouri, in 1954, and graduated from Truman High School and Columbia College at Columbia, Missouri. Howard established his career with stand-out roles in Full Metal Jacket and Ruby. In Till Death Us Do Part (1992), Howard portrayed author and attorney Vincent Bugliosi, who led the prosecution in the Tate-LaBianca murder trial. He has had a recurring role in the CBS weekly drama series Medium and has directed several episodes. Howard has extensive stage credits, including a role in the 2009 revival of August Wilson's Joe Turner's Come and Gone on Broadway. He also starred in and directed the films Big Bad Love and Dawn Anna, both co-written with James Howard, his brother. His wife, Debra Winger, stars in both films. He has two sons, one from a previous marriage and one with Winger (Babe Howard, born 1997).

Howard and Winger have appeared together in several productions at the American Repertory Theatre (ART) in Harvard Square, Cambridge, MA.

Howard and Winger have appeared together in several productions at the American Repertory Theatre (ART) in Harvard Square, Cambridge, MA.