[2] He has been associated with the Chicago experimental and improv scene, as well as with New York City when he relocated there in 2000 for his tenure as a member of American indie rock band Sonic Youth.

[4] O'Rourke has collaborated with Thurston Moore, Lee Ranaldo, Kim Gordon, Steve Shelley, Derek Bailey, Mats Gustafsson, Mayo Thompson, Brigitte Fontaine, Loren Mazzacane Connors, Merzbow, Nurse with Wound, Phill Niblock, Fennesz, Organum, Phew, Henry Kaiser and Flying Saucer Attack.

He has produced and instrumentally contributed to albums by artists such as Sonic Youth, Wilco, Stereolab, Superchunk, Kahimi Karie, Quruli, John Fahey, Smog, Faust, Tony Conrad, The Red Krayola, Bobby Conn, Beth Orton, and U.S.

[5] O'Rourke has previously been a member of Illusion of Safety, Brise-Glace with Darin Gray and Dylan Posa, Gastr Del Sol[5] with David Grubbs[6] and Sonic Youth.

[5] His most well-known works may be his series of releases on Drag City, which focus on more traditional songcraft: Bad Timing (1997), Eureka (1999), Insignificance (2001), The Visitor (2009) and Simple Songs (2015).