Offutt was born in Lexington, Kentucky, and is the son of author Andrew J. Offutt. He grew up in Haldeman, Kentucky, a former clay mining and brick manufacturing community of 200 people in the foothills of the Appalachian Mountains. Offutt quit high school to join the army, but failed the physical. He then attended Morehead State University and graduated with a degree in theater and a minor in art. He later attended the Iowa Writers' Workshop. In 1992, he published his debut short story collection, Kentucky Straight. His second book was the 1993 memoir The Same River Twice, and in 1997 he published his first novel, The Good Brother. In 1999, he published his second book of stories, Out of the Woods, followed in 2002 by No Heroes: A Memoir of Coming Home, about a visit he made back to Haldeman.