| Singer Songwriter | Okkervil River | 3:49 | |
| Hummingbird | Jeff Tweedy | 3:17 | |
| New Moon | Tweedy, Jeff Tweedy | 3:39 | |
| San Francisco Patrol | Robyn Hitchcock | 4:19 | |
| Northstar Blues | Magnolia Electric Co., Jason Molina | 5:08 | |
| Am I That Lonely Tonight? | Justin Townes Earle | 3:04 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| Bells Of Harlem | Dave Rawlings Machine | 4:07 | |
| Funeral Home - Live at The Vic, Chicago, IL - 10/20/17 | Daniel Johnston, Wilco | 3:10 | |
| South Tacoma Way | Neko Case | 4:51 | |
| One Fast Move or I'm Gone | Jay Farrar, Benjamin Gibbard | 4:15 | |
| Mama You've Been On My Mind / A Fraction of Last Thoughts on Woody Guthrie | Jack Johnson | 4:21 | |
| The Weekend | Dave Rawlings Machine | 5:29 | |
| Meadow of a Dream | The Felice Brothers | 4:00 | |
| Moment in the Sun | Clem Snide | 5:31 | |
| Muzzle of Bees | Wilco | 4:52 | |
| Last Days of Tecumseh | Grant Lee Buffalo | 1:02 | |
| Choir Of Angels | Deer Tick | 2:54 | |
| Tear Stained Eye - 2015 Remaster | Son Volt | 4:20 | |
| That's How I Got to Memphis | Karl Blau | 4:03 | |
| Plus Ones | Okkervil River | 3:43 | |
| Unlock more with Songs Like X Pro |
| I Know No Pardon | Vetiver | 6:53 | |
| Creosote | Son Volt | 4:12 | |
| The Poet Game | Greg Brown | 5:32 | |
| Screen Door | Uncle Tupelo | 2:42 | |
| $87 and a guilty Conscience That Gets Worse the Longer I Go | Richmond Fontaine | 3:34 | |
| Looking For A Place To Land | Justin Townes Earle | 3:28 | |
| Time Spent In Los Angeles | Dawes | 4:28 | |
| All of Your Might | Jay Farrar | 3:48 | |
| All the Best | My Morning Jacket | 3:16 | |
| If You've Gotta Go, Go Now - Bonus Track | J. Tillman | 3:45 | |
| Sweet Thing - 2006 Remaster | The Waterboys | 7:12 | |
| Tornado | Damien Jurado | 4:39 | |
| Warm (When The Sun Has Died) | Jeff Tweedy | 2:18 | |
| Through the Door | Israel Nash | 4:22 | |
| Still | Great Lake Swimmers | 2:51 | |
| Hammer Down | Magnolia Electric Co., Jason Molina | 4:05 | |
| Call It What You Will | Joe Pug | 2:56 | |
| Stranger In a Strange Land | Blitzen Trapper | 3:17 | |
| Guilty As a Saint | Chuck Prophet | 3:52 | |
| Little Ann | The Felice Brothers | 3:23 | |
| Hey Joe - Session at The loft, Chicago, IL - 10/19/17 | Daniel Johnston, Wilco | 2:35 | |
| Bugeye Jim | Billy Bragg, Wilco | 3:14 | |
| Woody | Hayden | 1:53 | |
| My Hometown | Whiskeytown | 2:45 | |
| One By One | Billy Bragg, Wilco | 3:25 | |
| Nothing Good | Ron Sexsmith | 2:54 | |
| Old L.A. | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 3:03 | |
| When The Roses Bloom Again | Billy Bragg, Wilco | 4:07 | |
