| History of Lovers | Calexico, Iron & Wine | 3:09 | |
| Off And Running | James McMurtry | 3:54 | |
| Katie Dear | The Felice Brothers | 3:58 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| Where Are You Tonight? | Cowboy Junkies | 5:05 | |
| West Texas Heaven | Kimmie Rhodes | 3:07 | |
| When Love Was Young | Iris DeMent | 3:38 | |
| Anniversary Song | Cowboy Junkies | 3:10 | |
| Rogers Park | Justin Townes Earle | 4:27 | |
| Wonderful Life | The Felice Brothers | 4:02 | |
| I Saw A Stranger With Your Hair | John Gorka | 4:03 | |
| Tell Me Again | Ron Sexsmith | 2:36 | |
| No Regrets - 2008 Remaster | Tom Rush | 3:51 | |
| You Took My Future | Teddy Thompson, Kelly Jones | 2:19 | |
| One Hell Of A Life | Katell Keineg | 3:35 | |
| Don't Remind Me - Commentary | Kelly Jones, Teddy Thompson | 1:07 | |
| Where I'm From | Shelby Lynne | 3:50 | |
| White Gardenias | Justin Townes Earle | 2:38 | |
| The Oil Rigs at Night | The Delines | 4:23 | |
| How Quickly Your Heart Mends | Courtney Marie Andrews | 3:45 | |
| Only Fooling | Teddy Thompson, Kelly Jones | 2:45 | |
| Unlock more with Songs Like X Pro |
| New York City's Killing Me (with The Pariah Dogs) | Ray LaMontagne, The Pariah Dogs | 4:13 | |
| Between Dark and Dawn | Nick Lowe | 2:31 | |
| Low Life Kingdom | Jay Farrar, Benjamin Gibbard | 3:20 | |
| Unknown Legend | Caitlin Canty | 3:55 | |
| Say Grace | Sam Baker | 4:19 | |
| Make a Wish on Me | Teddy Thompson, Kelly Jones | 2:16 | |
| Simple Twist of Fate | Jeff Tweedy | 3:43 | |
| Two Different Things | Caitlin Cary, Thad Cockrell | 4:16 | |
| Morning Song for Sally | Nanci Griffith | 4:55 | |
| Out of the Picture - 2015 Remaster | Son Volt | 3:48 | |
| So I'll Run | Jimmie Dale Gilmore | 3:52 | |
| Wichita Ain't so Far Away | The Delines | 2:31 | |
| Brother, Can You Spare A Dime (feat. Teddy Thompson) | Linda Thompson, Teddy Thompson | 2:47 | |
| Painting By Numbers | James McMurtry | 4:47 | |
| Sweet Is the Melody | Iris DeMent | 3:41 | |
| Strawberry Blonde | Ron Sexsmith | 3:41 | |
| Only Fooling | Kelly Jones, Teddy Thompson | 2:53 | |
| I Know | Kim Richey | 3:13 | |
| The Worst Is Yet To Come | Teddy Thompson | 4:26 | |
| Golden Ring | Jenni Muldaur, Teddy Thompson | 3:01 | |
| Tonight Will Be Fine | Teddy Thompson | 3:36 | |
| Family | Thompson, Teddy Thompson | 5:14 | |
| Lil' Wallet Picture | Richard Buckner | 4:32 | |
| Cherry Lane | Ryan Adams & The Cardinals | 4:31 | |
| The River Knows Your Name | John Hiatt | 4:25 | |
| Tragedy | Peter Wolf | 2:44 | |
| Through the Morning, Through the Night | Robert Plant, Alison Krauss | 4:00 | |
| Keep Your Distance | Buddy & Julie Miller | 3:49 | |
