“In Spite of Ourselves” was written by John Prine at the request of director Billy Bob Thornton for his film Daddy and Them — a domestic comedy set in rural Arkansas built around characters whose love for each other survives their persistent failure to be reasonable. Thornton asked Prine to write something about “two people who are falling in love but they both kind of suck.” The resulting song is a series of mutual insults delivered with increasing affection, the narrator and his partner cataloging each other’s failures as evidence of how well they fit together.
Prine released it as the title track of his 1999 album on Oh Boy Records — his thirteenth studio album and his first major project after successfully treating throat cancer, which had permanently altered the texture of his voice without diminishing its emotional authority. The album was structured as a series of duets with female vocalists, the title track pairing him with Iris DeMent. Other partners included Emmylou Harris, Lucinda Williams, Trisha Yearwood, Connie Smith, and Patty Loveless; “In Spite of Ourselves” was the only original Prine composition on the record, the rest being classic country covers.
Daddy and Them was completed before the album’s release but not distributed until 2001, leaving the song to find its audience through the record and live performances rather than the film. By the time the movie appeared, “In Spite of Ourselves” had already become one of the defining songs of Prine’s late period — a song about love as the decision to stay despite full knowledge of who the other person is.