| San Francisco | Jay Farrar, Benjamin Gibbard | 3:58 | ||
| Whip-poor-will | Magnolia Electric Co., Jason Molina | 4:12 | ||
| My Old Drunk Friend | Freakwater | 3:33 | ||
| Can't Sink This Town | Freedy Johnston | 3:52 | ||
| Ruby | Dave Rawlings Machine | 4:54 | ||
| Pass You By | Gillian Welch | 3:57 | ||
| I Fell into Painting Houses in Phoenix, Arizona | Richmond Fontaine | 3:27 | ||
| Handle With Care | Jenny Lewis, The Watson Twins | 2:56 | ||
| Something You Ain't Got | Cracker | 5:17 | ||
| Whistle on Occasion (feat. Chuck Prophet) | Kim Richey, Chuck Prophet | 2:36 | ||
| Wink | Blue Mountain | 3:17 | ||
| Keys | Golden Smog | 3:28 | ||
| Ford Econoline | Chuck Prophet | 3:41 | ||
| I Understand Now | Patterson Hood | 3:22 | ||
| Perfume | Old 97's | 3:04 | ||
| I Pray When I'm Drunk | Robyn Hitchcock | 2:06 | ||
| Poor, Poor LA | Tim Easton | 3:49 | ||
| After the Rain | Chuck Prophet | 3:35 | ||
| New American Language | Dan Bern | 5:12 | ||
| Christchurch Woman | Justin Townes Earle | 4:11 | ||
| Simple Twist of Fate | Jeff Tweedy | 3:43 | ||
| Unlock more with Songs Like X Pro | ||||
| Indianapolis | The Bottle Rockets | 3:32 | ||
| Barrier Reef | Old 97's | 3:49 | ||
| Screen Door | Uncle Tupelo | 2:42 | ||
| Bloody 98 | Blue Mountain | 2:47 | ||
| Fade Away | The V-Roys | 3:37 | ||
| Daisychain | Richard Buckner | 3:07 | ||
| Heat Lightning Rumbles in the Distance | Patterson Hood | 4:17 | ||
| All in One | Jay Farrar, Benjamin Gibbard | 2:07 | ||
| Acuff-Rose | Uncle Tupelo | 2:35 | ||
| Let's Go Running | Blue Mountain | 4:49 | ||
| Looking Forward to Seeing You | Golden Smog | 2:47 | ||
| Portland - 2008 Remaster | The Replacements | 4:28 | ||
| As Far As I Know | Paul Westerberg | 3:01 | ||
| Penthouse In The Woods | Scud Mountain Boys | 2:42 | ||
| Whiskey in My Whiskey | The Felice Brothers | 3:48 | ||
| Roll On | Josh Ritter | 4:16 | ||
| My Winding Wheel | Ryan Adams | 3:12 | ||
| Shaking Like a Flame | Glossary | 3:04 | ||
| Yesterday Cried | Golden Smog | 3:57 | ||
| Tiny Pieces | Bash & Pop | 4:36 | ||
| Unfortunately, Anna | Justin Townes Earle | 3:40 | ||
| The Ghost | Deer Tick | 3:31 | ||
| Fool King's Crown | Jay Farrar | 2:19 | ||
| Hammer Down | Magnolia Electric Co., Jason Molina | 4:05 | ||
| Never Felt Before | Golden Smog | 3:40 | ||
| Help Me, Suzanne | Rhett Miller | 3:44 | ||
| Bottom Of The World | Alejandro Escovedo | 3:04 | ||
| Goner w/ Souvenir | Richard Buckner | 2:41 | ||
