| Kentucky, 1988 | Kelsey Waldon | 4:04 | |
| From Outer Space | Jaime Wyatt | 4:13 | |
| That's How I Feel | Dori Freeman | 2:43 | |
| Love Is Just A Wrecking Ball | Del Barber | 4:20 | |
| Don't Think Twice. It's Alright | Susan Tedeschi | 4:43 | |
| Not That Simple | The Honeycutters | 3:24 | |
| Border Radio | Kelly Willis, Bruce Robison | 2:50 | |
| Sweet Dolly | Yarn | 4:22 | |
| Take it Out Back | Chuck Brodsky | 3:10 | |
| Coming Down | Bruce Robison, Kelly Willis | 2:40 | |
| Flat Top Guitar | Ana Egge | 2:50 | |
| King Cotton | The Secret Sisters | 3:12 | |
| Different Kind Of Gone | Mary Gauthier | 3:41 | |
| I'll Go to My Grave Loving You | Bruce Robison, Kelly Willis | 3:03 | |
| Giving up on Your Hometown | Lori McKenna | 3:15 | |
| Calm Before the Storm | Eliza Gilkyson | 3:50 | |
| Angel Flight | Darden Smith | 3:59 | |
| Time Stands Still | Chris Smither | 3:45 | |
| Slow on the Gulf | Tony Kamel | 3:47 | |
| Knowing How It Ends | Forest Sun | 2:53 | |
| Drive | Hayes Carll | 3:19 | |
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| End Like That | Bruce Robison | 4:39 | |
| Soulmate | Michael Dowdle, Brandon Fields, Jimmy Johnson, Kelly Willis | 3:57 | |
| River Girl | Kelley Mickwee | 4:47 | |
| Got Your Six | Mary Gauthier | 2:38 | |
| Christchurch Woman | Justin Townes Earle | 4:11 | |
| Not Forgotten You | Bruce Robison | 3:36 | |
| Take Me Down | Kelly Willis | 3:45 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| Hearts Beat and Take a Beating | Forest Sun | 3:16 | |
| Oh Set a Light | Chip Taylor, Carrie Rodriguez | 3:44 | |
| Love Is so Easy | Hayes Carll | 3:04 | |
| The Carolinian | Chatham County Line | 3:59 | |
| Prayer in Open D | Shannon McNally | 3:55 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| You Won't Find Me | Amelia Curran | 3:23 | |
| The Good Life | Bruce Robison | 2:49 | |
| Winsome Smile | Chris Smither | 3:34 | |
| On and On | Dead Horses | 3:37 | |
| If I Could Make You My Own | Dori Freeman | 3:22 | |
| Chuck Will's Widow - Video Mix | Amy Ray, The War And Treaty, Michelle Malone | 3:43 | |
| Angel from Montgomery | Bonnie Raitt | 4:11 | |
| Got You Covered | Blackie & The Rodeo Kings, Rosanne Cash | 3:47 | |
| Just Outside Of Austin | Lukas Nelson and Promise of the Real | 4:44 | |
| Ring Them Bells | Sarah Jarosz | 3:30 | |
| Friend Of Mine | Steve Martin, Edie Brickell | 2:36 | |
| Turn Off The News (Build A Garden) - Acoustic | Lukas Nelson and Promise of the Real | 3:01 | |
| Poor Boy's Delight | The Infamous Stringdusters | 4:07 | |
| Oh, Sister [Feat. Courtney Marie Andrews] | Logan Ledger, Courtney Marie Andrews | 3:40 | |