| Wake Up Time | Tom Petty | 5:19 | |
| Wondering Where The Lions Are | Bruce Cockburn | 3:43 | |
| Let the Mystery Be | 10,000 Maniacs | 3:08 | |
| I Hope That I Don't Fall In Love With You | Tom Waits | 3:53 | |
| Hard Bargain | Ron Sexsmith | 3:12 | |
| Acid Tongue | Jenny Lewis | 3:50 | |
| Clay Pigeons | John Prine | 4:27 | |
| Tell Me Anything (Turn to Gold) | Chuck Prophet | 3:22 | |
| Deep Red Bells | Neko Case | 4:03 | |
| Ohio | Crosby, Stills, Nash & Young | 3:03 | |
| Blue Canoe | Blue Mountain | 4:39 | |
| Hearts and Bones | Paul Simon | 5:39 | |
| Willin' | Little Feat | 2:54 | |
| Life Worth Livin' | Uncle Tupelo | 3:32 | |
| Paradise | John Prine | 3:15 | |
| He's Fine | The Secret Sisters | 3:43 | |
| Astral Weeks - 1999 Remaster | Van Morrison | 7:06 | |
| Come Pick Me Up | Ryan Adams | 5:18 | |
| What's So Funny 'Bout Peace, Love and Understanding? | Nick Lowe | 4:03 | |
| Lovin' in My Baby's Eyes | Taj Mahal | 2:40 | |
| Barrier Reef | Old 97's | 3:49 | |
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| Me & Jiggs | Josh Ritter | 3:04 | |
| Pacing The Cage | Bruce Cockburn | 4:40 | |
| All in One | Jay Farrar, Benjamin Gibbard | 2:07 | |
| Helpless | Crosby, Stills, Nash & Young | 3:37 | |
| Trouble | Ray LaMontagne | 4:01 | |
| Myrna Lee | Blue Mountain | 3:45 | |
| Summer's End | John Prine | 3:29 | |
| After the Rain | Chuck Prophet | 3:35 | |
| Dressed up Like Nebraska | Josh Rouse | 3:24 | |
| The Swimming Song | Loudon Wainwright III | 2:27 | |
| These Roads Don't Move | Jay Farrar, Benjamin Gibbard | 3:05 | |
| The Needle and the Damage Done | Neil Young | 2:02 | |
| Watch Me Fall | Uncle Tupelo | 2:12 | |
| Put the Message In the Box | World Party | 4:16 | |
| Darling One | Cracker | 4:43 | |
| To Be Without You | Ryan Adams | 3:21 | |
| Moonlight Mile - 2009 Mix | The Rolling Stones | 5:57 | |
| Hoping Machine | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 4:52 | |
| Trouble | The Jayhawks | 4:49 | |
| Poncho & Lefty | Townes Van Zandt | 3:40 | |
| Change | Blind Melon | 3:41 | |
| Red's Song | The Jayhawks | 3:58 | |
| Fly High | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 3:45 | |
| The Maker | Willie Nelson | 5:08 | |
| Hey Mama | Nathaniel Rateliff & The Night Sweats | 4:00 | |
| Bottomless Cup | The Jayhawks | 4:14 | |
| I Shall Be Released - Remastered 2000 | The Band | 3:12 | |
| Summer Blowin' Town | Ron Sexsmith | 2:18 | |
