In 1990, Stephen Jackson and Chris Watt met at Virginia Tech, through mutual friend Tal Bayer, who was attending nearby Radford University, and they formed a ska band called the Slugs with their former schoolmate Tom Goodin,[1] and an architecture classmate, Ben Gauslin.

The Pietasters recruited Jeremy Roberts, Toby Hansen, and Alan Makranczy as their new horn players, Rob Steward (Covington) on drums, and Paul Ackerman on keys.

By the end of the tour, the Pietasters began recording Oolooloo on Moon Ska with Victor Rice producing.

Oolooloo came out in the summer of 1995, after which bassist Chris Watt left the Pietasters to perform with Eastern Standard Time,[6] and Todd Eckhart moved from rhythm guitar to bass.

The video was filmed by Burning Toast Productions and featured scenes of the festival and live performance of the Pietasters playing their Jimmy Holiday cover, "The New Breed".

While backstage at a show in Los Angeles during a tour with the Mighty Mighty Bosstones, Tim Armstrong, guitarist with Rancid, and his business partner, Chris Qualiana,[9] approached the band and asked if they would join a new label they were creating, Hellcat Records, also featuring the Slackers, Hepcat and Dropkick Murphys.

Paul Ackerman and Tom Goodin left the band, as did bassist Todd Eckhardt, who was replaced by Jorge Pezzimenti.

[19][20][21][22] In late 2001, the Pietasters were recording their next album when they learned that former bassist, Todd Eckhardt, had died of a viral heart infection.

[14] The album caught the attention of James Brown, who asked the Pietasters to be his backing band at a sold-out concert in Washington DC in December 2002.