| Rachel's Song | James McMurtry | 4:39 | ||
| Rogers Park | Justin Townes Earle | 4:27 | ||
| After the Rain | Chuck Prophet | 3:35 | ||
| Sandusky | Uncle Tupelo | 3:43 | ||
| She Don't Have to See You | Golden Smog | 4:01 | ||
| Whiskey in My Whiskey | The Felice Brothers | 3:48 | ||
| The Mighty Midshipman | Centro-matic | 4:37 | ||
| Jackson Square | Mason Jennings | 4:10 | ||
| Lost Love | Jeff Tweedy | 2:28 | ||
| Back of a Bible | Patterson Hood | 4:28 | ||
| Movin' On | Justin Townes Earle | 4:41 | ||
| Let's Take Some Drugs and Drive Around | The Silos, Walter Salas-Humara | 4:17 | ||
| Two Different Things | Caitlin Cary, Thad Cockrell | 4:16 | ||
| Jenny of the Roses | Hiss Golden Messenger | 3:38 | ||
| Cigarettes Coffee and Booze | The Minus 5 | 4:24 | ||
| I Am Trying to Break Your Heart | Jeff Tweedy | 3:40 | ||
| Nicotine | Dead Man Winter | 3:20 | ||
| San Francisco | Jay Farrar, Benjamin Gibbard | 3:58 | ||
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | ||
| O! Grace | Magnolia Electric Co., Jason Molina | 3:27 | ||
| Heaven, Sittin' Down | Phosphorescent | 4:26 | ||
| Unlock more with Songs Like X Pro | ||||
| Bad Reputation | Freedy Johnston | 4:08 | ||
| New Moon | Tweedy, Jeff Tweedy | 3:39 | ||
| $87 and a guilty Conscience That Gets Worse the Longer I Go | Richmond Fontaine | 3:34 | ||
| Myrna Lee | Blue Mountain | 3:45 | ||
| Walk Where He Walked | Golden Smog | 2:49 | ||
| Red Rose Nantahala | Hiss Golden Messenger | 4:05 | ||
| To Be Young (Is to Be Sad, Is to Be High) | Ryan Adams | 3:04 | ||
| Ruby | Dave Rawlings Machine | 4:54 | ||
| Blue Canoe | Blue Mountain | 4:39 | ||
| Barstool Boys | Marah | 3:04 | ||
| Five Hearts Breaking | Alejandro Escovedo | 4:10 | ||
| Christchurch Woman | Justin Townes Earle | 4:11 | ||
| Barely Losing | Richmond Fontaine | 2:47 | ||
| No Depression | Uncle Tupelo | 2:20 | ||
| Brady | Backyard Tire Fire | 4:06 | ||
| Baby Learns to Crawl | Paul Westerberg | 2:46 | ||
| Nowhere Bound | Golden Smog | 3:48 | ||
| Hurricane Party | James McMurtry | 5:56 | ||
| Speed of the Sound of Loneliness | The Lemonheads | 2:46 | ||
| When the Circus Comes | Los Lobos | 3:16 | ||
| Daydreaming | Middle Brother, John McCauley, Matthew Vasquez, Taylor Goldsmith | 4:50 | ||
| Gone for Good - 2023 Remaster | The Shins | 3:12 | ||
| Chelsea Hotel '78 | Alejandro Escovedo | 3:30 | ||
| Sunspot Stopwatch | Pete Droge | 4:21 | ||
| The Maker | Willie Nelson | 5:08 | ||
| The Never-Ending Present | Gord Downie | 5:05 | ||
| It's A Wonderful Lie | Paul Westerberg | 2:47 | ||
| Six O'Clock News | Kathleen Edwards | 4:36 | ||
