| The Way It Goes | Gillian Welch | 4:01 | |
| In Spite of Ourselves (feat. Iris DeMent) | John Prine, Iris DeMent | 3:33 | |
| Run Like a Thief - 2008 Remaster | Bonnie Raitt | 3:02 | |
| Tequila Sunrise - 2013 Remaster | Eagles | 2:53 | |
| Sister Golden Hair | America | 3:19 | |
| Boots of Spanish Leather | Nanci Griffith | 5:17 | |
| Just a Song Before I Go | Crosby, Stills & Nash | 2:13 | |
| Angel from Montgomery | Bonnie Raitt | 4:11 | |
| Green River | Eilen Jewell | 2:57 | |
| The Guitar | Guy Clark | 4:03 | |
| Beautiful | Gordon Lightfoot | 3:23 | |
| Watching the River Run | Loggins & Messina | 3:26 | |
| Copperline | James Taylor | 4:21 | |
| (Goin') Wild for You Baby - 2008 Remaster | Bonnie Raitt | 5:25 | |
| Missin' You | Little Feat | 2:21 | |
| Waiting Around to Die | Townes Van Zandt | 2:45 | |
| Colorado | Stephen Stills | 2:52 | |
| Graceland | Justin Townes Earle | 3:14 | |
| Into the Mystic - 2013 Remaster | Van Morrison | 3:25 | |
| Iām In The Mood (feat. Bonnie Raitt) | John Lee Hooker, Bonnie Raitt | 4:31 | |
| Queen Bee | Taj Mahal | 4:40 | |
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| Dreamsicle | Jason Isbell and the 400 Unit | 3:44 | |
| You've Got a Friend - 2019 Remaster | James Taylor | 4:28 | |
| Anniversary Song | Cowboy Junkies | 3:10 | |
| Whiskey | Loggins & Messina | 1:57 | |
| If You Could Read My Mind | Gordon Lightfoot | 3:48 | |
| Desert Skies | The Marshall Tucker Band | 6:23 | |
| Sugar Babe | Jesse Colin Young | 3:41 | |
| You Don't Have to Cry - 2005 Remaster | Crosby, Stills & Nash | 2:42 | |
| If I Could Only Fly | Blaze Foley | 4:04 | |
| Give It Up or Let Me Go - 2008 Remaster | Bonnie Raitt | 4:29 | |
| Do I Ever Cross Your Mind | Ray Charles, Bonnie Raitt | 4:34 | |
| Wild Horses | Leon Russell | 3:37 | |
| Roll On | The Little Willies | 3:06 | |
| Hey Mama | Nathaniel Rateliff & The Night Sweats | 4:00 | |
| Walkin' After Midnight | Patsy Cline | 2:34 | |
| Who Knows Where The Time Goes? | Fairport Convention | 5:09 | |
| Breakdown | Tom Petty and the Heartbreakers | 2:43 | |
| A Pirate Looks At Forty | Jimmy Buffett | 3:55 | |
| Ophelia - Remastered 2000 | The Band | 3:32 | |
| A Song For You | Leon Russell | 4:08 | |
| Never Been To Spain - Single Version | Three Dog Night | 3:46 | |
| Drift Away | Dobie Gray | 3:54 | |
| When You Say Nothing At All | Alison Krauss & Union Station | 4:20 | |
| Find Yourself | Lukas Nelson and Promise of the Real | 6:16 | |
| If I Needed You | Townes Van Zandt | 3:44 | |
| Wild Horses | The Flying Burrito Brothers | 6:20 | |
| Pink Houses | John Mellencamp | 4:43 | |
| You'll Accomp'ny Me | Bob Seger | 4:00 | |