In 1974, when Bobby was only eight, he and his father (country musician Bobby Bare, Sr.) were both nominated for a Grammy Award for the song "Daddy What If", written by Shel Silverstein. Bare's daughter Isabella did a version of the song, which was featured on Twistable, Turnable Man, a tribute album to Shel Silverstein, co-produced by Bare and his father. He and his siblings also appeared on the television show Hee Haw when he was a child, to provide the witch scream on Bobby Bare, Sr.'s song "Marie Laveau"

He began playing guitar and songwriting, and started as a professional musician when he was about 30. Bare has said that he is someone who avoided "working a real job at any cost." He worked as a member of the road crew and as a light technician. Once he started writing and performing, he was offered contracts with Immortal Records and Lost Highway.

In the 1990s, he led the roots rock outfit Bare Jr., which was signed to Immortal Records, at that time the home of Korn and Incubus. They released two major label records, 1998's Boo-Tay and 2000's Brainwasher. They had a minor radio hit with "You Blew Me Off," which was featured in the movie Cruel Intentions and its soundtrack. The song was also performed on Late Night with Conan O'Brien on March 3, 1999.

In February 2016, Bare joined a new touring lineup of Robert Pollard's band, Guided by Voices, as guitarist along with Doug Gillard also on guitar, bassist Mark Shue and drummer Kevin March.

Many of Bare's songs incorporate a lot of humor and references to popular culture.His writing has been characterized as "inventive and melodic.” Shel Silverstein was a huge influence in his approach to songwriting. Bare describes it as writing poems and turning them into songs, which was very similar to what Silverstein did.