The Littlest Man Band was started by Scott Klopfenstein of Orange County, California. Scott was a long-time member of Reel Big Fish, a popular ska punk band. Scott had written a number of songs over the years that did not 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, the majority of whom are fellow ex-members of the band The Scholars.