The Littlest Man Band was started in 2003 by Scott Klopfenstein of Orange County, California. Scott is a long-time member of Reel Big Fish, a popular Ska band. Scott had written a number of songs over the years that didn't conform to the usual style of Reel Big Fish. He performed some of these by himself under the pseudonym "The Littlest Man" before being joined by several musicians well known to him from the Long Beach music scene. This differs from the music he and the fellow Reel Big Fish member Dan Regan had been performing previously