In 1986, Pierson and Ben Weasel co-founded the punk rock band Screeching Weasel in Chicago, Illinois. Pierson played guitar for the band until 2001.
In 2002, Pierson formed the acoustic pop-punk band Even in Blackouts, with which he has recorded three albums and one EP and toured several times.
Pierson is also a playwright and novelist, usually writing under the name Ian Pierce. He formed a theater production company, Hope And Nonthings, in 1990 and produced ten plays before joining the Neo-Futurists; he has been performing in their long-running show Too Much Light Makes the Baby Go Blind since 1996.
His semi-fictitious Weasels in a Box (2005) is a novelization of Screeching Weasel's history. His last novel, Last Temptation of Clarence Odbody, appeared in October 2011.