Before his ska and rock projects, Reese Roper was in the short-lived, Colorado-based, industrial metal group Exhumator. Members of that band joined with a larger cast of musicians to form the ska ensemble Five Iron Frenzy, who in 1996 signed with 5 Minute Walk recording studio. During this time Roper became known for his "vocal finesse" and, the ability to write lyrics with both a "tradition of ridiculousness" and a reverence for serious issues. The band was together until November 22, 2003, which is when they played their final show at the sold out Fillmore Auditorium in Denver, Colorado. Roper was both the lead vocalist and primary lyricist.