Bobby Bare Jr.

There's a strong case for predestination in the story of Bobby Bare Jr. He was born the son of a country hit machine, who passed on both his name and his talent. At the tender age of five, Bare Jr. had a cameo on what's been hailed as country music's first "outlaw" album, Bear Sr.'s Lullabys, Legends and Lies. The father-son duet netted them a Grammy nod.

Junior's own work defies even alt-country's sketchy borders. From the End of Your Leash (2004) took the thirtysomething singer-songwriter into pure pop territory and stranger points beyond. Like Shel Silverstein, author of the children's classic Where the Sidewalk Ends, who also penned the tunes for Lullabys, Bare Jr. typically deals with commonplace themes in a decidedly whacked-out manner. And whether by destiny or chance, Bobby Bare Jr. remains one of country music's more curious and creative offspring.