In April 2000 Superfly Presents asked Claypool to assemble a band to perform during New Orleans Jazz Fest. Claypool contacted Anastasio and together they agreed on mutual hero, Copeland. Oysterhead was originally intended to be a singular live performance at New Orleans Saenger Theatre on May 4, 2000. The band compiled a set of almost entirely original material for the show, practicing at Muskegon's Frauenthal Theatre. Tickets were scalped for up to $2,000 each, audience members included Francis Ford Coppola and Matt Groening. The band toured in 2001 and is scheduled to tour in 2021. Both times it has toured it has been interrupted due to significant disasters, both man-made and natural, in 2001 due to the September 11 attacks and in 2020 due to the COVID-19 pandemic.