The band's roots can be traced back to the summer of 1998. The founding members were Jose Silva and Steve Hall Jr. (pictured to the left attending a LeAnn Rimes concert in 1999.) One day in the summer of 1998, Steve was visiting Jose at his apartment in Novato, which he shared with John Leidel and Charlie Galletta. Jose had a 4-track recorder in his room, which he used to record the framework for several songs. Jose played three of the songs for Steve. Two of those three songs would later be released as the Wagon Band songs "Cry on Me" and "Future Boy". Steve was impressed upon hearing Jose's recordings, and went home to start working on some lyrics. The first draft he came up with for one of the songs was called "Liberty For Your Love".
For some reason, the lyrics did not fit too well with the music, and they have been lost ever since then. But Steve didn't give up. He went back to work and wrote the lyrics for another one of the songs, this time called "Cry on Me". Jose was very impressed with the lyrics, although they still needed some more work to be right for the song. When Jose and Steve could see they had a potential hit on their hands in 1999, they began looking around to see if anybody else would be interested in starting up a band. Jose also suggested that the band be called Pioneer Wagon. The Pioneer part of the name was because both Jose and Steve were regular pioneering at the time, while the Wagon part of the name would send an instant message that their intentions were to write country music. Eventually, a woman in the Tiburon area tried out to be the lead singer. However, the practice session went really bad, as the singer was intent on singing opera, instead of pop or country. Also, she rejected some of the lyrics to "Cry on Me", saying that she 'could never sing some of these words.' Thus, Jose and Steve moved on in their search for a singer and the band was stalled.
