Along for the ride is his close friend Stu Stone, who keeps Jamie in check to stick to their rap career.
From the beginning, Jamie expresses his dislike for fellow actor Jason Biggs (who, like Kennedy, appeared in Kevin Smith's 2001 film Jay and Silent Bob Strike Back).
Jamie and Stu also encounter many different rappers during the season, including Mike Jones, Ice-T, and a performance with the Three 6 Mafia.
Jamie and Stu also try to recruit special guests on their album, getting Bob Saget, formerly of the TV show Full House.
Robin Sloan Bechtel, an executive at Warner Bros. Records discovered Jamie Kennedy and Stu Stone's music on MySpace before the MTV show was greenlit.