| Artist | Song | Album | Label | Year | ||
| Johnny Cash | Next Hill We'll Be Home | Personal File | Columbia | 2006 | 8:00 | 3:00 |
| Reckless Sleepers | If We Never Meet Again | Single | IRS | 1982 | 8:03 | 4:00 |
| Steve Goodman | A Dying Pub's Fan Last Request | Affordable Art | Oh Boy | 1988 | 8:08 | 6:02 |
| Sam Phillips | One Day Late | A Boot and A Shoe | Virgin | 2004 | 8:14 | 3:11 |
| Chip Taylor | Yonkers, NY | Yonkers, NY | Train Wreck | 2009 | 8:17 | 4:20 |
| Buddy and Julie Miller | Don't Say Goodbye | Written in Chalk | New West | 2009 | 8:21 | 5:10 |
| Joe Henry | Light No Lamp | Blood from Stars | Anti | 2009 | 8:26 | 2:35 |
| Dave Rawlings Machine | Ruby | A Friend of a Friend | Acony | 2009 | 8:30 | 4:54 |
| Gillian Welch | I Wanna Sing the Rock and Roll | Time the Revelator | Acony | 2001 | 8:35 | 2:51 |
| Joe Ely | A Fllod on Our Hands | Sheets of Sin | Rounder | 2003 | 8:39 | 3:54 |
| Roseanne Cash | Silver Wings | The List | Manhattan | 2009 | 8:43 | 3:45 |
| Billy Bragg | Heart Like a Wheel | Reaching to the Converted | Rhino | 1999 | 8:46 | 2:46 |
| Emmy Lou Harris | Goin Back to Harlan | Wrecking Ball | Asylum | 1995 | 8:50 | 4:52 |
| Rufus Wainwright | Cigarettes and Chocolate Cigarettes and Chocolates | Poses | Dreamworks | 2005 | 8:55 | 4:00 |
| Watson Twins | Devil In You | Talking to You, Talking to Me | Vanguard | 2010 | 8:59 | 3:15 |
| Harry Nilson | I Guess the Lord Must Be In New York City | All Time Greatest Hits | RCA | 1969 | 9:04 | 2:35 |
| James Hunter | People Gonna Talk | People Gonna Talk | Rounder | 2008 | 9:06 | 4:00 |
| Bobby Hepp | Sunny | Soul Spectacular | Rhino | 1966 | 9:10 | 2:48 |
| Adele | Chasing Pavements | 19 | XL | 2008 | 9:12 | 3:30 |
| Avett Brothers | Laundry Room | I and Love and You | Ramsuer | 2009 | 9:16 | 5:51 |
| David Francey | Over You | The Waking Hour | Red House | 2004 | 9:23 | 3:00 |
| Laura Viers | I Can See Your Tracks | July Flame | Raven Marching Band | 2010 | 9:27 | 2:57 |
| Steve Earle | Lungs | Townes | New West | 2009 | 9:32 | 2:10 |
| Watson Twins | Harpeth River | Talking to You, Talking to Me | Vanguard | 2010 | 9:34 | 2:40 |
| Bob Dylan | Idiot Wind | Blood on the Tracks | Columbia | 1974 | 9:37: | 7:18 |
| Wilco | I'll Fight | Wilco the Record | Nonesuch | 2009 | 9:44 | 4:23 |
| Greg Brown | Boomtown | Poet Game | Red House | 1994 | 9:49 | 4:23 |
| Beattles | Dr. Robert | Revolver | Capitol | 1966 | 9:52 | 2:14 |
| Wendy Bird | Deliver Me | Natural Wonder | Beaumont- Classis | 2010 | 9:57 | 3:29 |
Playlist: The Bonnie Simmons Show for January 28, 2010 - 8:00pm
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