Tim O'Brien was born left-handed but taught himself to play guitar, fiddle, mandolin, banjo, bouzouki and mandocello right-handed, a feat of adaptation that mirrors how he rewired his entire career. This episode follows the Wheeling, West Virginia native from the Bob Dylan record his sister Molly played him at age 12, through dropping out of Colby College in 1973 with 200 songs memorized as his startup capital, to Boulder, Colorado, where he co-founded Hot Rize in 1978.

The conversation unpacks Hot Rize's swinging take on traditional bluegrass, the comedic alter ego band Red Knuckles and the Trailblazers, the sibling duo albums with Molly on Sugar Hill, and how the O'Briens recorded the first published versions of Gillian Welch's Orphan Girl and Wichita. It also covers being dropped by RCA, founding Howdy Skies Records in 1999, touring with ...