He is the primary songwriter and recording artist of The Cairo Gang, one half of The Double alongside drummer Jim White, one third of The CIA and a founding member of Clinamen.

He has contributed vocal and instrumental work to a variety of international musical projects, appearing on recordings by the likes of Bonnie "Prince" Billy, Ty Segall, Angel Olsen, Azita, Joan of Arc, Edith Frost,[1] Women and Children, John Webster Johns, Jeff Harms, Chicago poet/singer Marvin Tate,[2] Matteah Baim, Japanese musician Takuma Watanabe, Earth Girl Helen Brown, Joshua Abrams and Rob Mazurek.

Kelly has toured in several of the aforementioned acts in addition to with Baby Dee, CFM, Mikal Cronin, Sonny Smith, Beth Orton, and Terry Reid; and in other instances, performed live with Chan Marshall, Scott Tuma, Joan of Arc, and Pillars and Tongues.

haha's main objective is to disassociate from digital media platforms and to exist entirely in physical form, including hardcopy newsletters.

In 2010 Drag City released the critically acclaimed album, The Wonder Show of the World,[7][8][9] which featured compositional work by Kelly as The Cairo Gang, along with the single, Midday/You Win, and the 10’’, Island Brothers/New Wonder.

[10] In 2024, Kelly started the band Hard Quartet, an underground rock supergroup including Jim White (drummer), Stephen Malkmus & Matt Sweeney.