| Strange Feelin' | Tim Buckley | 7:40 | |
| Five Thousand and One | Lee Hazlewood | 3:02 | |
| 22nd Century | Nina Simone | 8:43 | |
| You Were Sent to This World | Johnnie Frierson | 3:09 | |
| The Beginnings of Bop | Jack Kerouac | 1:58 | |
| Aviator - 2011 Remaster | Michael Chapman | 9:30 | |
| The Parasite (For Buffy) | Eugene McDaniels | 9:34 | |
| Come Sing Me a Happy Song to Prove We Can All Get Along the Lumpy Bumpy Long and Dusty Road | Bert Jansch | 2:01 | |
| Juliane | Lionel Belasco & His Orchestra | 2:59 | |
| Me and the Wine and the City Lights | Lee Hazlewood | 2:21 | |
| Baby Where You Are | Ted Lucas | 2:32 | |
| Can't Get Away from My Love | Jackson C. Frank | 2:50 | |
| Trouble Is a Lonesome Town | Lee Hazlewood | 4:26 | |
| Whatevershebringswesing - 1999 Remaster | Kevin Ayers | 8:13 | |
| Pray Them Bars Away | Lee Hazlewood | 2:49 | |
| I'm Going in a Field | The Ivor Cutler Trio | 2:09 | |
| Southern Nights | Allen Toussaint | 3:30 | |
| 2 Excerpts from On the Road: No. 2, So in America | David Amram, Jack Kerouac, Estelle Parsons | 2:27 | |
| Thinking of the Day | Leo Nocentelli | 2:35 | |
| Who Knows Where the Time Goes - Live | Nina Simone | 4:57 | |
| Blue Mountain | Michael Hurley | 6:20 | |
| Unlock more with Songs Like X Pro |
| The Big Noise From Winnetka | Bob Crosby & The Bob Cats | 2:37 | |
| Bowery Blues (with Steve Allen) | Jack Kerouac | 3:52 | |
| Don't Look Back | Jackson C. Frank | 2:57 | |
| Olive | Ken Nordine | 1:33 | |
| I'm The Jungle Man | C.W. Stoneking | 2:59 | |
| Happy Time | Tim Buckley | 3:16 | |
| If You're Goin' to the City | Mose Allison | 3:50 | |
| Witchi Tai To - Remastered Version | Harpers Bizarre | 2:42 | |
| Sweet Jazz Music | Jelly Roll Morton | 1:46 | |
| Trouble Trouble | Betty Roche | 5:36 | |
| The Drum | Slapp Happy | 3:35 | |
| My Baby | Ken Nordine, The Fred Katz Group | 2:34 | |
| Yip Roc Heresy | Slim Gaillard And His Orchestra | 2:33 | |
| Woncha Come On Home | Joan Armatrading | 2:39 | |
| A Supermarket In California - Live / 1/29/1959 | Allen Ginsberg | 2:17 | |
| Some Days There Just Ain't No Fish | Hoagy Carmichael | 2:35 | |
| Title Music from Merchant Ivory's film BOMBAY TALKIE | Shankar Jaikishan | 2:32 | |
| Okolona River Bottom Band | Bobbie Gentry | 3:04 | |
| Wrap Your Troubles In Dreams | Nico | 5:06 | |
| Long Journey | Michael Hurley | 2:51 | |
| Medley: San Francisco Blues (Fragments) | Jack Kerouac | 3:02 | |
| Blue Horizon | Sidney Bechet | 4:24 | |
| Faretheewell (Fred's Tune) | Fred Neil | 4:01 | |
| 900 Miles | Terry Callier | 5:07 | |
| Paper Mountain Man | Linda Perhacs | 3:14 | |
| When My Baby Left Me | Furry Lewis | 3:23 | |
| Ba-Di-Da | Fred Neil | 3:38 | |
| The Great Grandfather | Bo Diddley | 2:26 | |
