| A Little More Time | John Doe | 3:48 | ||
| Heaven, Sittin' Down | Phosphorescent | 4:26 | ||
| One Fast Move or I'm Gone | Jay Farrar, Benjamin Gibbard | 4:15 | ||
| Wave | Joe Henry | 4:30 | ||
| New Drink for the Old Drunk | Crooked Fingers | 3:52 | ||
| Can't Sink This Town | Freedy Johnston | 3:52 | ||
| That Girl From Brownsville Texas | Jim White | 6:22 | ||
| Last Days of Tecumseh | Grant Lee Buffalo | 1:02 | ||
| Until The Led | Vic Chesnutt | 3:38 | ||
| San Francisco | Jay Farrar, Benjamin Gibbard | 3:58 | ||
| Credit | Chuck Prophet | 4:29 | ||
| Disappointed Man | Freedy Johnston | 3:15 | ||
| Mission | Joe Henry | 3:42 | ||
| Reasons To Quit | Phosphorescent | 3:13 | ||
| Borrowed Wings | Jim White, Suzie Ungerleider | 4:34 | ||
| Age of Miracles | Chuck Prophet | 4:09 | ||
| Sausalito | Conor Oberst | 3:10 | ||
| One Too Many Mornings | Joe Henry | 3:28 | ||
| Idle Tomorrows | The Sadies | 3:28 | ||
| The Longer You Wait | Richmond Fontaine | 2:38 | ||
| Evie's Tears | Freedy Johnston | 3:01 | ||
| Unlock more with Songs Like X Pro | ||||
| Pollyanna | Patterson Hood | 4:37 | ||
| Point Breeze | Marah | 2:14 | ||
| Never Again | The Sadies | 2:36 | ||
| History of Lovers | Calexico, Iron & Wine | 3:09 | ||
| The Sweet Part of the City | The Hold Steady | 4:24 | ||
| Fast Man | Frank Black | 4:12 | ||
| Post To Wire | Richmond Fontaine | 2:13 | ||
| Sadly Beautiful - 2008 Remaster | The Replacements, Jay Healy | 3:17 | ||
| Hanging on to You | Jay Farrar | 2:51 | ||
| The Midnight Special | Billy Bragg, Joe Henry | 3:34 | ||
| Old Friends | Chuck Prophet | 3:56 | ||
| Why Not Your Baby | Velvet Crush | 4:48 | ||
| Gravity of the Situation | Vic Chesnutt | 4:09 | ||
| Wrecking Ball | Gillian Welch | 4:56 | ||
| Handcuffed To A Fence In Mississippi | Jim White, Morecheeba | 4:08 | ||
| The Next Messiah | Jenny Lewis | 8:45 | ||
| Oh! Susanna (Live) | Stephen Foster, Chris Walden, Joe Henry, Cincinnati Pops Orchestra, John Morris Russell | 3:50 | ||
| The Conquering Sun | Gord Downie, The Sadies | 3:09 | ||
| Mixtape | Tift Merritt | 3:18 | ||
| Drank Like A River | Whiskeytown | 2:57 | ||
| Anchor | Alejandro Escovedo | 3:30 | ||
| Born For Me | Paul Westerberg | 4:01 | ||
| Six O'Clock News | Kathleen Edwards | 4:36 | ||
| The Maker | Willie Nelson | 5:08 | ||
| Fireman's Wedding | Joe Henry | 4:23 | ||
| Like She Was A Hammer | Joe Henry | 4:27 | ||
| Tears Rolling Up Our Sleeves | Paul Westerberg | 3:28 | ||
| Always A Friend | Alejandro Escovedo | 3:35 | ||
