Fifteen formed in 1988 during the tail end of the Crimpshrine tour while Ott and Curran were writing songs together. After Crimpshrine broke up, Fifteen embarked on their first tour, in the summer of 1989. During this time, Jean Repetto played drums. Although the band drove across the country, they only played a handful of shows on this first tour. Upon returning from tour, Mike Goshert took over drums. Fifteen recorded their debut EP in April 1990 for Lookout! Records. Fifteen went on a more substantial tour in the summer of 1990 with Filth and Econochrist. Mark Moreno took over on drums and they recorded their first full-length album, Swain's First Bike Ride, in December 1990. In 1991, Rich "Lucky Dog" Gargano joined the band on bass. Curran switched over to second guitar briefly, before leaving the band in 1992. In summer of 1992, the band toured the US and Canada, and recorded their second album, The Choice of a New Generation. Afterwards, Lucky Dog and Mark Moreno left the band and Curran returned, joined by Jesse Wickman on drums. The band released their second EP and third album with Chris Flanagan on drums, and went on three more US tours before their first and only European tour in fall of 1994. Afterwards, Curran left for good.