In Spite of Ourselves is John Prine's 1999 album, produced by Jim Rooney and released on Oh Boy Records. This unique project features Prine performing duets with some of the most renowned female vocalists in country and folk music, including Iris DeMent, Emmylou Harris, Lucinda Williams, and Patty Loveless. The album primarily consists of classic country covers, with the title track "In Spite of Ourselves" being the only original song by Prine.

The tracks highlight the playful, tender, and sometimes humorous aspects of relationships, with Prine and his duet partners bringing a fresh perspective to each song. The album's minimalist production emphasizes the vocal performances and the chemistry between Prine and his collaborators, making In Spite of Ourselves a standout in Prine's discography and a favorite among fans of traditional country and folk music.

1. John Prine /w Iris DeMent - (We're Not) The Jet Set
2. John Prine /w Connie Smith - So Sad (To Watch Good Love Go Bad)
3. John Prine /w Lucinda Williams - Wedding Bells/Let's Turn Back The Years
4. John Prine /w Trisha Yearwood - When Two Worlds Collide
5. John Prine /w Melba Montgomery - Milwaukee Here I Come
6. John Prine /w Emmylou Harris - I Know One
7. John Prine /w Dolores Keane - It's A Cheating Situation
8. John Prine /w Patty Loveless - Back Street Affair
9. John Prine /w Connie Smith - Loose Talk
10. John Prine /w Iris DeMent - Let's Invite Them Over
11. John Prine /w Fiona Prine - 'Til A Tear Becomes A Rose
12. John Prine /w Dolores Keane - In A Town This Size
13. John Prine /w Iris DeMent - We Could
14. John Prine /w Melba Montgomery - We Must Have Been Out Of Our Minds
15. John Prine /w Iris DeMent - In Spite Of Ourselves
16. John Prine - Dear John ( I Sent Your Saddle Home)