October 14, 2021
- 5:00am Wheels On Fire by Ian & Sylvia on Dylan, Cash, and the Nashville Cats: A New Music City
- 5:03am A Night In Summer Long Ago by Mark Knopfler on Golden Heart
- 5:08am One Too Many Mornings by Bob Dylan on The Bootleg Series, Vol. 4: The 'Royal Albert Hall' Concert [Disc 2]
- 5:12am Seven Days by Kenny Chesney on Hemingway's Whiskey (Deluxe Edition)
- 5:17am Step Inside This House by Lyle Lovett on Step Inside This House - Disc 1 (MCA)
- 5:22am Storm Windows by John Prine on Great Days: The John Prine Anthology Disc 2 (Rhino)
- 5:27am The High Notes (feat. The Grascals) by Shawn Byrne on Pine Trees, Cheap Wine, And the Moon
- 5:31am Billy The Kid by Marty Robbins on Essential Country & Western
- 5:35am The Healing Kind by Lee Ann Womack on I Hope You Dance (MCA)
- 5:37am Hemingway's Whiskey by Guy Clark on Somedays The Song Writes You (Dualtone)
- 5:40am I'm Blowin' Away by Joan Baez on Blowin' Away
- 5:43am Sweet as Sweet Comes by Robbie Fulks on Upland Stories
- 5:47am Hello Where Are You? by Kristin Andreassen on Kiss Me Hello
- 5:50am Hopelessly Yours (with Lee Greenwood) by Suzy Bogguss on Greatest Hits (Liberty Records)
- 5:53am Waltz For Mr. B by Alison Brown on The Company You Keep (Compass Records)
- 5:56am River Jordan by Secret Sisters on Put Your Needle Down (Republic Records)
- 5:59am When I Fall In Love by Bill Evans on The Solo Sessions, Vol. 1
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