| Better Than | Lake Street Dive | 3:35 | |
| Last Kind Words | Rhiannon Giddens | 4:13 | |
| Give Me Love | Applewood Road, Fats Kaplin | 2:50 | |
| Father and Daughter | Paul Simon | 4:11 | |
| Let's Be Still | The Head And The Heart | 4:28 | |
| The Times They Are a-Changin' - Live at Madison Square Garden, New York, NY - October 1992 | Tracy Chapman | 3:02 | |
| Hard Times Come Again No More | Stephen C. Foster, Yo-Yo Ma, James Taylor, Edgar Meyer, Mark O'Connor | 3:43 | |
| House of Stone | Watchhouse | 3:16 | |
| Sweet Baby James - 2019 Remaster | James Taylor | 2:53 | |
| No Not Me | Pieta Brown | 4:19 | |
| Suitcase Full of Sparks | Gregory Alan Isakov | 3:56 | |
| Dead Mans Will | Calexico, Iron & Wine | 3:13 | |
| Such Great Heights | Iron & Wine | 4:11 | |
| Dream in Blue | The Stray Birds | 3:32 | |
| Fare Thee Well (Dink's Song) | Oscar Isaac, Marcus Mumford | 3:00 | |
| You're Gonna Make Me Lonesome When You Go | Miley Cyrus | 3:31 | |
| San Luis | Gregory Alan Isakov | 4:32 | |
| Sweet Love of Mine (Acoustic) | Joy Williams | 2:55 | |
| You Can Close Your Eyes - 2019 Remaster | James Taylor | 2:29 | |
| Sweet Child o' Mine | Taken By Trees | 5:02 | |
| New York City's Killing Me (with The Pariah Dogs) | Ray LaMontagne, The Pariah Dogs | 4:13 | |
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| The Observatory | The White Buffalo | 3:47 | |
| America | First Aid Kit | 3:38 | |
| Follow the Water | Calexico, Iron & Wine | 3:45 | |
| Guiding Light | Foy Vance, Ed Sheeran | 5:52 | |
| Leave The Light On | Chris Smither | 3:47 | |
| Shelter from the Storm | Bob Dylan | 5:01 | |
| History of Lovers | Calexico, Iron & Wine | 3:09 | |
| Crack The Case | Dawes | 5:54 | |
| Love Is All | The Tallest Man On Earth | 4:14 | |
| Billie Jean | The Civil Wars | 4:19 | |
| The Trouble with Wanting | Joy Williams | 3:55 | |
| Crazy Love - 2013 Remaster | Van Morrison | 2:35 | |
| Midas Tongue | Sam Beam, Jesca Hoop | 3:03 | |
| Up Above My Head | Rhiannon Giddens | 3:09 | |
| Wildflowers in the Graveyard | Amber Rubarth | 3:00 | |
| Catch the Wind | Donovan | 2:53 | |
| Humble & Kind | Lori McKenna | 4:03 | |
| Re: Stacks | Bon Iver | 6:41 | |
| Alright Alright | Birds of Chicago | 4:02 | |
| Speaking With The Angel | Cry Cry Cry | 4:01 | |
| When Fall Comes To New England | Cheryl Wheeler | 3:16 | |
| Language Of The Heart | David Wilcox | 4:42 | |
| I Still Haven't Found What I'm Looking For | Sarah Jarosz | 3:32 | |
| Always Will | Steve Martin, Edie Brickell | 2:25 | |
| January Wedding | The Avett Brothers | 3:48 | |
| If I Could Talk To A Younger Me | Béla Fleck, Abigail Washburn | 3:22 | |
| Where I Am Now | Shelby Lynne | 3:40 | |
| I'm By Your Side | Steve Martin, Edie Brickell | 2:35 | |