Brothers Bobby and Billy Shaddox were exposed to music from an early age. Their father, Tom, would croon acoustic lullabies like “Danny’s Song “ and “House at Pooh Corner” at the side of their crib. From early on, Billy showed a fondness for the guitar and, following in the tradition of his father and grandfather, he diligently learned chords and basic finger-picking patterns. Billy says that in his early teens, Jimi Hendrix fired his imagination and led him to explore rock, blues, country, and bluegrass. Bobby focused his interests towards singing.

The brothers at first explored their musical talents separately. It wasn’t until junior college that Billy joined Bobby’s group, which was renamed from Sgt. X to Naked Jumpies. The band later split, due to artistic differences, and the brothers drifted apart musically. After other unsuccessful attempts to find the right mix, and over a backyard bonfire, the pair met Chris Greenspan and Billy Midnight was formed.

Their CD Live at the Trade Winds includes nine songs that vary from folk to Americana to bluegrass influences. A 2008 album, Don't Get Your Hopes Up, won Best Americana Or Country Album at the '08 San Diego Music Awards. The album was recorded and mixed by Jason Hee and mastered by Mike Kamoo at his Earthling Studio. The cover art was drawn by Billy Shaddox.

Chris Greenspan left the group, and then singer Billy Midnight accepted a job in Salt Lake City, placing the band on an extended hiatus. Bassist Jason Hee plays with the Buzzkill Romantics.

Their first show in sixteen months happened April 14, 2012, at the Ruby Room, with singer Billy Shaddox flying in from his current Salt Lake City, Utah residence.