Born in 1976 and originally residing in Brighton, Michigan, Dilloway began going to basement shows in Ann Arbor during the mid-'90s. Inspired by local noise rock band Couch and experimental art rock bands Caroliner and Sun City Girls, he formed a discordant, lo-fi rock band called Galen. The group's first show was an opening slot for Couch. Dilloway eventually joined Couch, playing drums on a West Coast tour as well as a 1995 7". Galen's first 7" EP was co-released by Bulb Records (run by Couch's Pete Larson and Magas) and Dilloway's newly formed Hanson Records. The label also released cassettes by Andrew W.K.'s early project Ancient Art of Boar, which Dilloway also recorded with. Dilloway and Galen's Steve Kenney began experimenting with tape loops, synthesizers, and delay pedals, forming a project called Isis and Werewolves. In 1997, as Dilloway moved to Ann Arbor, the label released an experimental collage tape by Nate Young performing under the name Wolf Eyes. Young and Dilloway performed a few gigs together under the jokey moniker Michigan Wolverines (also the name of the University of Michigan's football team), but eventually they just referred to the duo as Wolf Eyes. Dilloway also joined Universal Indians, an improvisational noise group influenced by free jazz as well as hardcore punk. Universal Indians' John Olson joined Wolf Eyes, and their music morphed from punk-based industrial rock (as on their 2000 self-titled EP on Bulb Records) to more experimental, improvisation-heavy noise. However, Olson and Dilloway also went back to their punk roots with Violent Ramp, a skateboarding-themed hardcore band.
Wolf Eyes became restlessly prolific, documenting their performances and rehearsals with dozens (eventually hundreds) of limited cassettes and CD-R releases, primarily issued by either Hanson or Olson's American Tapes. Wolf Eyes' 2001 albums Slicer and Dread received notice from the greater indie music world, and the band released the Dead Hills EP on Troubleman Unlimited in 2002. A tour with Black Dice led to a split LP by the two groups (issued by Fusetron in 2003), and eventually Wolf Eyes shocked everyone by signing with Sub Pop for 2004's Burned Mind, which turned out to be one of their most brutal, ugly recordings yet. Dilloway soon left Wolf Eyes, however, as he became stressed out from the constant touring. His final session with Wolf Eyes was for a Peel Session that unfortunately ended up being recorded a week after John Peel died in October of 2004. Dilloway temporarily relocated to Nepal, where his wife, Erika Hoffmann (vocalist for Godzuki, Saturday Looks Good to Me, His Name Is Alive, and other Michigan indie pop bands), was studying, and Hair Police's Mike Connelly replaced Dilloway in Wolf Eyes. Dilloway constantly recorded audio while in Nepal, and after he returned to the States, he issued a set of field recordings and Nepalese pop songs called Sounds of Nepal, as well as Radio Nepal, a series of recordings taped off Nepalese radio. He incorporated further Nepalese recordings into his subsequent solo work.
Around 2007, he moved to Oberlin, Ohio and began collaborating with numerous Ohio-based artists, including Emeralds and Robert Turman. In early 2012, he released a long-in-the-making double LP titled Modern Jester, which featured some of his most rhythmic compositions to date. The release received excellent reviews and has often been referred to as his best work. Also in 2012, he collaborated with Jason Lescalleet on a more drone-based album titled Grapes and Snakes, released by Bill Kouligas' Pan label. In 2013, Dilloway contributed to Wolf Eyes' No Answer: Lower Floors album, which was hailed as one of their best works. Later in the year, he opened up his Hanson Records shop in Oberlin. Popeth, a further collaboration with Lescalleet, was released in 2014. Subsequent releases included collaborations with Bill Nace and Dylan Nyoukis. In 2017, Dais Records released Dilloway's full-length The Gag File. Referred to as the follow-up to Modern Jester, the album incorporated vocal manipulations similar to his live performances. Along with the regular flow of limited tape releases, Dilloway spent parts of 2019 and 2020 collaborating with German abstract electronic artist Lucrecia Dalt. Their joint work was released in July 2021 as the full-length album Lucy Aaron, issued on Dilloway's Hanson imprint. That November, he joined Body/Head's Kim Gordon and Bill Nace for Body/Dilloway/Head, a hypnotic mesh of drones and edits that was released by Three Lobed Recordings as part of the label's 20th Anniversary series. ~ Paul Simpson, Rovi