| Carry Me Home | Hem | 5:15 | |
| Mamah Borthwick (A Sketch) | Conor Oberst | 3:56 | |
| Black Star (Live) | Gillian Welch | 5:18 | |
| Powderfinger | Cowboy Junkies | 5:45 | |
| No Matter What | Marc Cohn, Aimee Mann | 3:41 | |
| One For Sorrow, Two For Joy | The Innocence Mission | 4:04 | |
| Carson's Last Supper | Suzanne Vega | 3:30 | |
| Idle (The Rabbit Song) | Hem | 3:44 | |
| Outside of Space and Time | David Byrne, St. Vincent | 4:18 | |
| The Temptation of Adam | Josh Ritter | 4:12 | |
| Strangle All Romance | Emily Haines & The Soft Skeleton | 2:36 | |
| July | Karen Peris, Don Peris, Mike Bitts, The Innocence Mission | 3:22 | |
| Pins and Needles | Margaret Glaspy | 3:26 | |
| You Left Me With an Ocean | Waxahatchee | 2:16 | |
| Name of the Game (feat. Aimee Mann) | Susanna Hoffs, Aimee Mann | 4:48 | |
| Rollercoasters | Aimee Mann | 3:44 | |
| You're the One I Love (feat. Fiona Apple) | Sara Watkins, Fiona Apple | 1:45 | |
| Julie Julie (From "Difficult People") | Julie Klausner, Aimee Mann | 2:40 | |
| Not Over By Half | Joan Shelley | 4:33 | |
| Cross Bones Style | Cat Power | 4:32 | |
| Dope Van Gogh | Jenny O. | 3:19 | |
| Unlock more with Songs Like X Pro |
| When I Was Drinking | Hem | 3:44 | |
| Werewolf | Fiona Apple | 3:12 | |
| Make a Plan to Love Me | Bright Eyes | 4:13 | |
| Season of Hollow Soul | k.d. lang | 4:55 | |
| Mary On A Wave | Okkervil River | 5:11 | |
| Pass in Time | Beth Orton | 7:17 | |
| River Low | Joan Shelley | 3:31 | |
| Crazy Feels | Oh Pep! | 4:53 | |
| Horsey | Hem | 3:34 | |
| Aspera | Erin McKeown | 4:27 | |
| High On The Mountain | Joan Shelley | 3:49 | |
| Singer’s No Star | Waxahatchee | 3:58 | |
| How Am I Different - Remastered 2020 | Aimee Mann | 5:03 | |
| Now | Edie Brickell & New Bohemians | 6:02 | |
| All The Right Reasons | The Jayhawks | 3:24 | |
| New York - piano version | St. Vincent | 2:48 | |
| Smoking Section - piano version | St. Vincent | 4:11 | |
| I Do | Edie Brickell & New Bohemians | 2:00 | |
| Calling It Quits | Aimee Mann | 4:09 | |
| Happy Birthday, Johnny | St. Vincent | 2:58 | |
| Mixtape | Tift Merritt | 3:18 | |
| Ventura | Lucinda Williams | 4:41 | |
| This Eye | Edie Brickell & New Bohemians | 3:17 | |
| Sylvia Plath | Ryan Adams | 4:10 | |
| Pink Flamingos | Rickie Lee Jones | 6:33 | |
| Lonely Sinking Feeling | Cowboy Junkies | 4:24 | |
| She | Edie Brickell & New Bohemians | 5:07 | |
| Lost In Space | Aimee Mann | 3:28 | |
