| Imogene | Cory Branan | 3:51 | |
| Just Us Kids | James McMurtry | 5:08 | |
| Singer Songwriter | Okkervil River | 3:49 | |
| Lumberlung | Slobberbone | 4:28 | |
| The Vow | Cory Branan | 5:02 | |
| Fine Foods Market | Tim Barry | 3:19 | |
| Go West | Austin Lucas | 4:11 | |
| Jackson | Rumbleseat | 2:37 | |
| Cigarettes Coffee and Booze | The Minus 5 | 4:24 | |
| All the Labor | The Gourds | 3:17 | |
| Screen Door | Uncle Tupelo | 2:42 | |
| All These Little Cowboys | Cory Branan | 7:27 | |
| Katherine Belle | American Aquarium | 3:28 | |
| Neapolitan Bridesmaid | Tarkio | 2:37 | |
| Americano | Roger Clyne & The Peacemakers | 3:53 | |
| Bottom Dollar Boy | Vandoliers | 3:20 | |
| Smashed | Buffering the Vampire Slayer, Cory Branan, Jenny Owen Youngs | 2:42 | |
| Sidelong | Sarah Shook & the Disarmers | 4:10 | |
| Rex's Blues | Son Volt - Jay Farrar & Kelly Willis | 4:40 | |
| North Star | Joel Plaskett Emergency | 4:52 | |
| Jolene | Cory Branan | 3:49 | |
| Unlock more with Songs Like X Pro |
| I'll Be Around | Bobby Bare Jr. | 4:36 | |
| When My Baby's Beside Me | Jason Isbell and the 400 Unit | 3:25 | |
| Box Full of Letters - 2017 Remaster | Wilco | 3:04 | |
| Hummalong | The Drams | 4:39 | |
| Song Songs | Old Man Markley | 2:16 | |
| Paperwings | Damien Jurado | 2:53 | |
| Wasteland | Dead Man Winter | 4:42 | |
| When You're Outta Your Mind - Download-Only Bonus Track | Chris Wollard & The Ship Thieves | 3:33 | |
| Fomula Cola, Dollar Draft | Marah | 4:43 | |
| Pinball Song | Slobberbone | 4:36 | |
| Gimmeakiss | The Avett Brothers | 2:13 | |
| Wantin' Her Again | Ben Kweller | 2:42 | |
| Tough Love | Joel Plaskett Emergency | 3:44 | |
| Crazy | Lydia Loveless | 5:52 | |
| Song for My Roommates | Drag The River | 2:47 | |
| Slowly (Oh So Slowly) | Conor Oberst | 3:34 | |
| Someday | Middle Brother, John McCauley, Matthew Vasquez, Taylor Goldsmith | 3:40 | |
| Long Island Sound | James McMurtry | 6:47 | |
| Fuck Up | Sarah Shook & the Disarmers | 3:21 | |
| Yeah Sapphire | The Hold Steady | 3:36 | |
| The Prettiest Waitress in Memphis - Live Session, Memphis, TN, 2019 | Jam in the Van, Cory Branan | 3:08 | |
| Bad Man | Cory Branan | 3:54 | |
| Learn to Say No | Lydia Loveless | 4:14 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| Some New Town | Slobberbone | 4:56 | |
| Let It Ride | Ryan Adams & The Cardinals | 3:23 | |
| Gimme A Sign | Ryan Adams | 3:03 | |
| Peaceful Valley | Ryan Adams & The Cardinals | 3:42 | |
