| Accidentally Like a Martyr | Warren Zevon | 3:06 | |
| Down By The Henry Moore | Blackie & The Rodeo Kings | 4:02 | |
| Borderless Love | The Flatlanders | 3:16 | |
| Train of Glory | Jonathan Edwards | 2:28 | |
| Got Your Six | Mary Gauthier | 2:38 | |
| My Sweet Annette | Drive-By Truckers | 3:51 | |
| Mama's Little Baby | Delbert McClinton & The Dick50 | 3:08 | |
| Wishing All These Things Were New | Merle Haggard | 3:20 | |
| I'm Tellin' You (feat. Holly Williams) | John Prine, Holly Williams | 1:50 | |
| Down to Seeds and Stems Again | Bill Kirchen | 4:02 | |
| Gonesville | Bob Weir | 4:07 | |
| Perfect Timing | Drive-By Truckers | 2:57 | |
| I Sang The Song | Mac Wiseman, John Prine, Peter Cooper, Thomm Jutz | 3:35 | |
| Bear Creek Blues | John Prine | 4:45 | |
| I Thought the Wreck Was Over | The Flatlanders | 2:45 | |
| Hold On I | Chris Smither | 4:03 | |
| Everybody Knows Her | Jonathan Edwards | 1:53 | |
| Drunk Girl | Fred Eaglesmith | 3:09 | |
| My Dog and Me | John Hiatt & The Goners | 3:15 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Bend in the Water | Gordon Lightfoot | 3:00 | |
| Unlock more with Songs Like X Pro |
| Lookin' for Me Somewhere | Bodeans | 3:01 | |
| Trouble Is | Justin Townes Earle | 3:22 | |
| Train Home | Chris Smither | 4:25 | |
| L.A. | Lukas Nelson and Promise of the Real | 3:35 | |
| Dirty Life and Times | Warren Zevon | 3:15 | |
| Been Around a Long Time | Delbert McClinton & Glen Clark | 3:38 | |
| Captain's Song (Sorley Boy) | The Orphan Brigade, John Prine | 3:11 | |
| Missing Pieces | John Hiatt & The Goners | 4:06 | |
| Leave My Heart Alone | Pure Prairie League | 4:24 | |
| Crossroads - 2008 Remaster | Ry Cooder | 4:24 | |
| Sixteen Angels Dancing 'Cross the Moon | Chip Taylor, John Prine | 3:18 | |
| The Perfect Time | The Subdudes | 4:01 | |
| Black Rose | Billy Joe Shaver | 2:44 | |
| Same Thing Happened to Me | John Prine | 3:18 | |
| 36 Cents | The Bacon Brothers | 4:24 | |
| Knob & Tube | Colin Linden | 3:14 | |
| To Live Is To Fly | Townes Van Zandt | 3:15 | |
| Burn Your Playhouse Down | George Jones, Keith Richards | 2:53 | |
| Heart A Mine | Blackie & The Rodeo Kings, Mary Margaret O'Hara | 3:56 | |
| Drinkin' Days | Slaid Cleaves | 4:25 | |
| I Am A Lonesome Fugitive | Roy Buchanan | 3:44 | |
| Sam Stone | Nathaniel Rateliff, John Prine | 4:17 | |
| When Sinatra Played Juarez | Tom Russell | 3:37 | |
| Broke Down | Slaid Cleaves | 3:10 | |
| A Kiss Before I Go | Ryan Adams & The Cardinals | 2:04 | |
| Always A Friend | Alejandro Escovedo | 3:35 | |
| Rollin' Home | Elvin Bishop | 4:57 | |
| Anchor | Alejandro Escovedo | 3:30 | |
