As a child in Michigan, Dilloway was “really into horror movies and rubber masks and Fangoria magazine.” Later he would incorporate a rubber mask into his standard performance practice as a noise musician, noting that it embodied a fascinating coexistence of creepiness and goofiness (Pitchfork). 

Wolf Eyes was founded in 1996 by Nate Young and joined not long thereafter by Dilloway (in 1998) and John Olson (in 2000), who had already collaborated in the band Universal Indians. Over the course of its existence, Wolf Eyes has released over 100 recordings on diverse labels, including Dilloway’s own Hanson Records, Sub Pop and Hospital Productions, and has cooperated with musicians like Anthony Braxton, Black Dice and Prurient. Dilloway was an integral force behind the band’s success for seven years. His relocation to Nepal was partially inspired by an obsession with field recordings and led to the release of a 4 CD box set, Sounds of Nepal. By the time he returned to the US just seven months later, Mike Connelly had taken his place in the band; anyway, Dilloway wanted to avoid touring and focus on his solo music.  

Dilloway’s output as a solo artist is informed by his parallel fixations on synthesizers and 8-track tape loops. His attention to one medium or the other shifts cyclically: “I’ll spend my winters working on synth music and then all the other time I‘m usually working with my tapes,” he told Pitchfork. He also uses tape echo machines, contact mics (which he sometimes places directly in his mouth) and a tape recorder for the blind created by the Library of Congress. His double LP Modern Jester accumulated all of his musical infatuations into a single “bipolar” package “...of drama and humor.” In recent years Dilloway has collaborated with drummers Chris Corsano and Ryan Jewell. In 2012 he and musician Jason Lescalleet released the album Grapes and Snakes on PAN.

In 1997 he released, via Hanson, the first Wolf Eyes album, a self-titled cassette, in 1997. Hanson has also put out essential material by Kevin Drumm, Smegma, Hive Mind, Emeralds, and others.