In 1989, Jefferson Airplane reunited for a tour and eponymous album on Epic Records. In between sets, lead guitarist Jorma Kaukonen and bassist Jack Casady performed as Hot Tuna. After attending a show and seeing the positive reaction to Hot Tuna, Epic executives offered them a recording contract. Kaukonen produced the album, and described the sessions as easy-going, with songs requiring minimal takes. He and Casady were joined by Michael Falzarano on rhythm guitar and Harvey Sorgen on drums.
Compared with previous albums, Kaukonen has relatively few writing credits, with the rest made up of blues covers, songs from contemporary writers, and originals from newcomer Falzarano. It also features a cover of the 1960s protest song "Eve of Destruction," intended as a comment on the then-current Gulf War. (A cover of "Endless Sleep" was also recorded during the sessions, and later released on Live at Sweetwater Two.) In a press interview, Kaukonen described the choice of material: "I picked out songs I can still relate to. My whole era of songwriting back in the '70s, I sort of refer to as the 'canyons of your mind' songwriting school, though, and I don't find it easy to relate to those bizarre, introspective songs anymore."