December 23, 2019
- 5:03am The Wrong Girl by Lee Ann Womack on Greatest Hits
- 5:06am This Love Is Real by John Prine on Lost Dogs + Mixed Blessings (Oh Boy)
- 5:10am The Truck Song by Lyle Lovett on My Baby Don't Tolerate (Lost Highway)
- 5:12am Old And In The Way by Old & In The Way on Old And In The Way
- 5:16am I Will Rise Up / Ain't No More Cane by Lyle Lovett & His Large Band on It's Not Big It's Large (Curb/Lost Highway)
- 5:23am Be Proud Of The Gray In Your Hair by Dave Evans on Oxford American Southern Music, No. 19: Kentucky
- 5:27am You're Not A Drop In The Bucket by The Earls Of Leicester on The Earls Of Leicester
- 5:30am Cross My Broken Heart by Suzy Bogguss on Greatest Hits (Liberty Records)
- 5:34am My Crazy by Kristin Andreassen on Kiss Me Hello
- 5:37am Sinai To Canaan - Part 2 by Chris Thile on Not All Who Wander Are Lost
- 5:41am I'd Understand Why by The Hot Club Of Cowtown on The Best of The Hot Club of Cowtown (Shout Factory)
- 5:43am The Night They Drove Old Dixie Down by Joan Baez on Greatest Hits
- 5:47am Ghosts by Jesse Winchester on A Reasonable Amount Of Trouble (Appleseed Recordings)
- 5:52am Iuka by Secret Sisters on Put Your Needle Down (Republic Records)
- 5:56am Song For Rudell (Stitch) by Mickey Clark & the Blue Norther on Reasons & Rhymes (Sona Blast Records)
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