| # | Title | Artist | Length |
|---|
| 1 | (We’re Not) The Jet Set | John Prine w/ Iris DeMent | 2:37 |
| 2 | So Sad (to Watch Good Love Go Bad) | John Prine w/ Connie Smith | 2:30 |
| 3 | Wedding Bells / Let’s Turn Back the Years | John Prine w/ Lucinda Williams | 3:48 |
| 4 | When Two Worlds Collide | John Prine w/ Trisha Yearwood | 2:22 |
| 5 | Milwaukee Here I Come | John Prine w/ Melba Montgomery | 2:22 |
| 6 | I Know One | John Prine w/ Emmylou Harris | 2:41 |
| 7 | It’s a Cheating Situation | John Prine w/ Dolores Keane | 2:57 |
| 8 | Back Street Affair | John Prine w/ Patty Loveless | 2:48 |
| 9 | Loose Talk | John Prine w/ Connie Smith | 2:45 |
| 10 | Let’s Invite Them Over | John Prine w/ Iris DeMent | 2:11 |
| 11 | ’Til a Tear Becomes a Rose | John Prine w/ Fiona Prine | 2:50 |
| 12 | In a Town This Size | John Prine w/ Dolores Keane | 3:31 |
| 13 | We Could | John Prine w/ Iris DeMent | 2:17 |
| 14 | We Must Have Been out of Our Minds | John Prine w/ Melba Montgomery | 2:17 |
| 15 | In Spite of Ourselves | John Prine w/ Iris DeMent | 3:34 |
| 16 | Dear John (I Sent Your Saddle Home) | John Prine | 2:27 |