Dwyer started making lo-fi experimental music in the late '90s when he was still based in Providence, where he grew up. Solo material as Orinoka Crash Suite appeared on compilations, and he participated in noise rock groups like Landed and Burmese, who were affiliated with the city's notorious Load Records. After moving to San Francisco, Dwyer formed the Lightning Bolt-inspired duo Pink Brown, with Jeff Rosenberg as drummer and Dwyer singing and playing guitar. Under the alias Hans Bunschlapen, Dwyer performed in the homoerotic electro-industrial dance group Zeigenbock Kopf. He also formed the noisy garage rock band Coachwhips, who achieved their lo-fi sound by using a telephone transducer as a microphone.
Dwyer began releasing music under the shortened OCS name in 2003, with a self-titled double album consisting of a CD containing acoustic songs and a second disc of noise improvisations. OCS gradually became Dwyer's main project, as his other acts disbanded, although he also played in short-lived groups like the Hospitals and Yikes. Along with percussionist and musical saw player Patrick Mullins, OCS released 3 4 on Narnack Records in 2005. Brigid Dawson joined the band for 2006's The Cool Death of Island Raiders, billed to the OhSees. 2007's Sucks Blood, as the Oh Sees, marked the first release on Castle Face, the label co-founded by Dwyer. By 2008, the band amended their name to Thee Oh Sees and settled into a four-piece lineup featuring bassist Petey Dammit and drummer Mike Shoun, and their sound crystallized into a signature brand of psychedelic garage punk. The band earned much acclaim for their blistering live shows as well as their inventive albums and EPs, which appeared at a rapid pace on labels like In the Red, Captured Tracks, and Castle Face.
While mainly busy playing in Thee Oh Sees and running his label, Dwyer occasionally participated in the free jazz trio Sword Sandals. After relocating to Los Angeles, he launched his synth-based solo project, Damaged Bug, in 2014. Thee Oh Sees shifted their lineup but remained active, while Dwyer and Dawson revived OCS for 2017's Memory of a Cut Off Head. As Oh Sees, the band released some of their heaviest material yet, from 2017's Orc to 2019's Face Stabber. Shortening the name to Osees, the group issued several albums in 2020, including the motorik psych-punk release Protean Threat.
In 2020, Dwyer started releasing a series of improvised group efforts recorded at his house, blending jazz fusion and Krautrock influences. Bent Arcana was the first, and it featured TV on the Radio's Kyp Malone, Mr. Elevator's Tomas Dolas, percussionist Ryan Sawyer, and several others. Witch Egg followed in early 2021, featuring Dolas and saxophonist Brad Caulkins from the previous album, as well as drummer Nick Murray and bassist Greg Coates. Next up was the more challenging Endless Garbage, which featured the freewheeling, splattery percussion of Ted Byrnes. Moon-Drenched followed, featuring much of the cast of Bent Arcana as well as electric pianist Ben Boye and saxophonist Joce Soubrian. The year concluded with the release of Gong Splat, which included Coates and Sawyer as well as percussionist Andres Renteria and synth player Wilder Zoby. ~ Paul Simpson, Rovi