| The Man Who Couldn't Cry | Loudon Wainwright III | 6:15 | ||
| Dwight Yoakam | Sarah Shook & the Disarmers | 3:40 | ||
| Down to Seeds and Stems Again | Bill Kirchen | 4:02 | ||
| Lazy Third Eye | Willy Tea Taylor, The River Arkansas | 4:06 | ||
| Oklahoma Gypsy Shuffler | Adam Carroll | 4:45 | ||
| Sadder Day | Western Centuries | 4:30 | ||
| The Terrible Sunrise | Bobby Bare Jr. | 3:07 | ||
| Let Him Roll | Guy Clark | 4:03 | ||
| Deguello Motel | Roger Alan Wade | 4:00 | ||
| Blackberry Winter | James McMurtry | 5:09 | ||
| Still Drunk, Still Crazy, Still Blue | Scott H. Biram | 2:56 | ||
| Bull Riders & Songwriters | Willy Tea Taylor | 5:15 |