| Empty Hearted Town | Warren Zevon | 3:06 | |
| Señor (Tales of Yankee Power) | Willie Nelson, Calexico | 5:17 | |
| Heaven and Hell | Waylon Jennings, Willie Nelson | 1:38 | |
| I Think Its Going to Work Out Fine | Ry Cooder | 4:44 | |
| On Your Side | Aaron Lee Tasjan | 4:03 | |
| Maybe California | Neal Casal | 4:34 | |
| Reckless | Rodney Crowell | 3:30 | |
| Detroit or Buffalo | Barbara Keith | 4:31 | |
| Lay Me Down (with Willie Nelson) | Loretta Lynn, Willie Nelson | 2:50 | |
| Fair Play | Van Morrison | 6:14 | |
| No Reason to Quit | Merle Haggard, Willie Nelson | 3:15 | |
| Mandolin Wind | Amy Helm | 5:52 | |
| The Watchman's Gone | Gordon Lightfoot | 4:18 | |
| Ballad of Easy Rider | The Byrds | 2:04 | |
| Missin' You | Little Feat | 2:21 | |
| When Will I Be Changed (feat. Bob Weir) | Josh Ritter, Bob Weir | 5:52 | |
| Got Your Six | Mary Gauthier | 2:38 | |
| Irene Wilde | Alejandro Escovedo | 2:51 | |
| Behind the Ritual | Van Morrison | 6:56 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| Moonlight In Vermont | Willie Nelson | 3:23 | |
| Unlock more with Songs Like X Pro |
| The Damage | Rodney Crowell | 4:01 | |
| Pick Up the Tempo | Waylon Jennings, Willie Nelson | 2:34 | |
| Jerusalem Tomorrow | David Olney | 5:09 | |
| Say Grace | Sam Baker | 4:19 | |
| (The) Most Unoriginal Sin | Willie Nelson | 4:48 | |
| It Ain't Over Yet | Rodney Crowell, Rosanne Cash, John Paul White | 5:14 | |
| Salford Sunday | Richard Thompson | 4:08 | |
| Emerald Street | Eliza Gilkyson | 3:45 | |
| Left Alone | Malcolm Holcombe, Iris DeMent | 4:11 | |
| Willin' | Little Feat | 2:54 | |
| Cry Like a Rainstorm - 2008 Remaster | Bonnie Raitt | 3:55 | |
| Workin’s Too Hard | Rayna Gellert | 3:36 | |
| Tattler | Ry Cooder | 4:19 | |
| I'll Be All Right | Jorma Kaukonen | 3:08 | |
| You Ain't Going Nowhere | Nitty Gritty Dirt Band | 3:52 | |
| I've Just Destroyed The World | Willie Nelson | 2:52 | |
| Tell Heaven | Rosanne Cash | 2:40 | |
| The Banks of the Leopold Canal | The Deep Dark Woods | 6:08 | |
| A Feather's Not A Bird | Rosanne Cash | 3:18 | |
| Superman | Snoop Dogg, Willie Nelson | 2:05 | |
| Carolina Rain | Ryan Adams | 5:23 | |
| Beatnik Walking | Richard Thompson | 3:54 | |
| Always A Friend | Alejandro Escovedo | 3:35 | |
| Just Outside Of Austin | Lukas Nelson and Promise of the Real | 4:44 | |
| Entella Hotel | Peter Case | 4:58 | |
| Wild Horses | The Flying Burrito Brothers | 6:20 | |
| Forget About Georgia | Lukas Nelson and Promise of the Real, Lucius | 8:17 | |
| At The Crossroads - Alternate Mix | Sir Douglas Quintet | 4:37 | |
