| Start a War | The National | 3:16 | ||
| My Name Is Carnival | Jackson C. Frank | 3:44 | ||
| Northstar Blues | Magnolia Electric Co., Jason Molina | 5:08 | ||
| Rock Bottom Riser | Smog | 5:44 | ||
| Blue Valentines | Tom Waits | 5:50 | ||
| I Can Hardly Spell My Name | Lambchop | 3:24 | ||
| Tell Me Why | Neil Young | 2:57 | ||
| Somewhere over the Rainbow | Mark Kozelek | 2:29 | ||
| Ballad of Lou the Welterweight | The Felice Brothers | 5:00 | ||
| Buckskin Stallion Blues | Amy Annelle | 3:21 | ||
| After the Gold Rush | Neil Young | 3:45 | ||
| It's A Motherfucker | Eels | 2:11 | ||
| Hard Times | Gillian Welch | 4:52 | ||
| Green, Green Rocky Road | Oscar Isaac | 3:17 | ||
| I Think I Need a New Heart | The Magnetic Fields | 2:32 | ||
| Song for the Asking | Simon & Garfunkel | 1:50 | ||
| We Are Nowhere and It's Now | Bright Eyes | 4:12 | ||
| I'm a Man You Don't Meet Every Day | The Pogues | 2:55 | ||
| Send in the Clowns | Mark Kozelek | 3:56 | ||
| Keep Me in Your Heart | Warren Zevon | 3:28 | ||
| Dreaming My Dreams With You | Cowboy Junkies | 4:31 | ||
| Unlock more with Songs Like X Pro | ||||
| Strange Feelin' | Tim Buckley | 7:40 | ||
| Bookends Theme - Reprise | Simon & Garfunkel | 1:20 | ||
| Mockingbirds | Grant Lee Buffalo | 4:40 | ||
| Grace Kelly Blues | Eels | 3:35 | ||
| Martha | Tom Waits | 4:28 | ||
| Katie Cruel | Karen Dalton | 2:22 | ||
| Heaven - 2005 Remaster | Talking Heads | 4:01 | ||
| The Book of Love | The Magnetic Fields | 2:42 | ||
| Pleasant Street | Tim Buckley | 5:17 | ||
| As Tears Roll By | Daniel Lanois | 3:55 | ||
| Day After Tomorrow | Tom Waits | 5:58 | ||
| If I Could Only Fly | Blaze Foley | 4:04 | ||
| As You Can See | Micah P. Hinson | 2:19 | ||
| Accidentally Like a Martyr | Warren Zevon | 3:06 | ||
| How Does It Feel | Roy Harper | 6:27 | ||
| A Sight For Sore Eyes | Tom Waits | 4:40 | ||
| Is This Desire? | PJ Harvey | 3:25 | ||
| Find The River | R.E.M. | 3:49 | ||
| Forget It | Rodríguez | 1:50 | ||
| I'm Your Man - Live | Nick Cave | 4:31 | ||
| Right In Time | Lucinda Williams | 4:36 | ||
| Silver Words? | Rodríguez | 2:04 | ||
| I Want To See The Bright Lights Tonight | Richard & Linda Thompson | 3:09 | ||
| Cause | Rodríguez | 5:30 | ||
| Be Not So Fearful | Bill Fay | 2:44 | ||
| Place To Be | Nick Drake | 2:40 | ||
| Buffalo Ballet | John Cale | 3:28 | ||
| A Night In | Tindersticks | 6:25 | ||
