| Papa Was a Rodeo | The Magnetic Fields | 5:01 | ||
| Kansas City | Okkervil River | 5:46 | ||
| Ballad of Big Nothing | Seth Avett & Jessica Lea Mayfield | 2:34 | ||
| Springtime Of The Year | Kacy & Clayton | 2:58 | ||
| Mourning Glory | Harry Nilsson | 2:14 | ||
| Muse Blues | Loudon Wainwright III | 2:53 | ||
| Five Year Kansas Blues | F. J. McMahon | 2:46 | ||
| 200 More Miles | Cowboy Junkies | 5:29 | ||
| Ballerina - 1999 Remaster | Van Morrison | 7:03 | ||
| If Only You Were Lonely - Twin Tone Single Version | The Replacements | 2:37 | ||
| Braver Newer World | Jimmie Dale Gilmore | 5:00 | ||
| Swimming Song | Kate & Anna McGarrigle | 2:29 | ||
| School Days | Loudon Wainwright III | 3:05 | ||
| Melt Your Heart | Jenny Lewis, The Watson Twins | 2:52 | ||
| The Beast in Me | Nick Lowe | 2:28 | ||
| Michigan Girls | Califone | 4:00 | ||
| Can't Get Away from My Love | Jackson C. Frank | 2:50 | ||
| I Love You | Lou Reed | 2:18 | ||
| Are You Here For The Festival | Michael Hurley | 3:56 | ||
| Stars in My Life | The Flatlanders | 3:20 | ||
| History of Lovers | Calexico, Iron & Wine | 3:09 | ||
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| Only Someone Running | Bonnie Prince Billy, Matt Sweeney | 3:13 | ||
| To Love Is To Bury | Cowboy Junkies | 5:16 | ||
| Little Ann | The Felice Brothers | 3:23 | ||
| Hotter Than Mojave in My Heart | Iris DeMent | 2:33 | ||
| Going down the road feeling bad | Elizabeth Cotten | 2:12 | ||
| Love's Enough | David Ackles | 3:19 | ||
| Bell Bottom Pants | Loudon Wainwright III | 2:28 | ||
| Sweet Lil' gal (23rd/1st) | Ryan Adams | 3:38 | ||
| South of the South | David Dondero | 5:11 | ||
| Morning Glory | Tim Buckley | 2:51 | ||
| Beast For Thee | Bonnie Prince Billy, Matt Sweeney | 3:41 | ||
| I'm So Lonesome I Could Cry | Cowboy Junkies | 5:25 | ||
| I Believe in You | Lambchop | 3:27 | ||
| Friday Night Fever | Silver Jews | 2:44 | ||
| Song For Jainie | Tim Buckley | 3:01 | ||
| You and Your Sister | Chris Bell | 3:11 | ||
| It's Alright to Linger | Elyse Weinberg | 2:47 | ||
| October | Jackson C. Frank | 4:04 | ||
| If I Had the World to Give | Bonnie Prince Billy | 2:37 | ||
| I Hear You Calling | Bill Fay | 2:54 | ||
| Sweet Lucy | Michael Hurley, Unholy Modal Rounders, Jeffrey Frederick & The Clamtones | 4:06 | ||
| Galbraith Street | Ron Sexsmith | 3:05 | ||
| Everything Happens | Fred Neil | 2:19 | ||
| Lebanon, Tennessee | Ron Sexsmith | 2:57 | ||
| The Lady Came From Baltimore | Tim Hardin | 1:49 | ||
| Green Rocky Road | Fred Neil | 3:40 | ||
| The Lost Ones | Ted Hawkins | 3:12 | ||
| Muskrat Love (Muskrat Candlelight) | Willis Alan Ramsey | 3:23 | ||
