Long interested in cutting-edge art, Orcutt has a master's in English and has made several experimental short films, one of which he sold to MTV in 1990. He also played in several local punk bands, most notably the Trash Monkeys, before forming Harry Pussy in 1992 with his then-wife, drummer Adris Hoyos. They worked together for the next five years, releasing a series of uncompromising and confrontational recordings on small labels and gaining acclaim from the likes of Sonic Youth's Thurston Moore and Sebadoh's Lou Barlow. Toward the tail-end of Harry Pussy's existence in 1996, Orcutt completed his first solo recording, titled simply Solo CD (otherwise referred to as "Untitled"). It was issued by the New York-based Audible Hiss label, and featured guest vocals from Hoyos as well as instrumental contributions from drummer Danny Arad and saxman Joe Cohen, among others.
Following Harry Pussy's breakup and the couple's divorce, Orcutt moved to San Francisco and took an extended break from music in order to concentrate on filmmaking. He resumed performing and releasing records in 2009, creating a label called Palilalia Records in order to issue his work. His style had developed into a brash, startling variation of blues playing, performed mainly on acoustic guitar. Following several limited 7" and LP releases, and a well-received performance on free-form radio station WFMU (recorded in the station's bathroom), Editions Mego began issuing Orcutt's work in 2011. The Austrian label reissued his 2009 album A New Way to Pay Old Debts, and released its follow-up, How the Thing Sings, as well as 2013's A History of Every One, which included unrecognizable renditions of songs such as "White Christmas" and "Zip-A-Dee-Doo-Dah."
Orcutt has performed at numerous festivals as a solo artist, and he's also collaborated with several other well-regarded experimental musicians, including drummer Chris Corsano, free jazz artist Peter Brötzmann, and cellist Okkyung Lee. Orcutt also released a split LP with Sir Richard Bishop (formerly of Sun City Girls) in 2014, and electric album Colonial Donuts with drummer Jacob Felix Heule in 2015. In 2017, he released a self-titled electric album that was surprisingly less abrasive than his acoustic work. The next year, Orcutt and Corsano paired up for the frenetic and punky collaborative album Brace Up! While the duo had issued several limited-edition records at this point, the spiky energy of this explosive album was one of their more widely visible and critically celebrated. In 2019, Orcutt returned with the more subdued solo collection Odds Against Tomorrow. A further collaboration with Corsano, Made Out of Sound, arrived in 2021. The minimalist, melodic Music for Four Guitars appeared in 2022. ~ Steve Huey & Paul Simpson, Rovi