The Tail Draggers originally got together to play a gig for some private pilots having a barbecue in a hanger at Montgomery Field. Deciding to reflect that first gig with their name, they called themselves Captain Noonan and the Tail Draggers in reference to Amelia Earhart's navigator on her last flight and the type of plane in which they were lost. As time passed, they found themselves using the shortened name the Tail Draggers.

As of 2019, violinist John Mailander (Plow) was playing with Bruce Hornsby.