| China Grove | The Doobie Brothers | 3:15 | |
| New York State of Mind | Billy Joel | 6:02 | |
| Dream Weaver | Gary Wright | 4:16 | |
| Willin' | Little Feat | 2:54 | |
| It Ain't Over Yet | Rodney Crowell, Rosanne Cash, John Paul White | 5:14 | |
| Uncle John's Band - 2013 Remaster | Grateful Dead | 4:44 | |
| Carmelita | Warren Zevon | 3:34 | |
| Millworker | James Taylor | 3:51 | |
| Brandy (You're a Fine Girl) | Looking Glass | 3:06 | |
| Astral Weeks - 1999 Remaster | Van Morrison | 7:06 | |
| Good Time Charlie's Got the Blues | Danny O'Keefe | 3:00 | |
| Only the Good Die Young | Billy Joel | 3:55 | |
| My Back Pages | The Byrds | 3:08 | |
| Takin' It to the Streets | The Doobie Brothers, James Taylor | 3:51 | |
| Carolina In My Mind | James Taylor | 5:01 | |
| Sandman | America | 5:08 | |
| After the Gold Rush | k.d. lang | 4:00 | |
| Oh Baby, Don't You Loose Your Lip on Me - 2019 Remaster | James Taylor | 1:49 | |
| Kind & Generous | Natalie Merchant | 4:01 | |
| Photographs and Memories | Jim Croce | 2:08 | |
| If I Needed You | Lyle Lovett | 3:46 | |
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| Wild Night | Van Morrison | 3:33 | |
| Hard Times Come Again No More | Stephen Foster, Yo-Yo Ma, James Taylor, Edgar Meyer, Mark O'Connor | 3:43 | |
| Sunny Skies - 2019 Remaster | James Taylor | 2:21 | |
| Remember When the Music (Reprise) | Harry Chapin | 3:52 | |
| Free Man in Paris | Joni Mitchell | 3:03 | |
| American Girl | Tom Petty and the Heartbreakers | 3:34 | |
| Monday Morning | Fleetwood Mac | 2:47 | |
| Crawling Back To You | Tom Petty | 5:05 | |
| Intone My Servant | Seals and Crofts | 3:04 | |
| Don't Ask Me Why | Billy Joel | 2:57 | |
| Mr. Tambourine Man | The Byrds | 2:29 | |
| Another Park, Another Sunday | The Doobie Brothers | 4:27 | |
| Me & Magdalena | The Monkees | 3:33 | |
| Rainy Day Man - Remastered | James Taylor | 3:00 | |
| Wild Horses - 2009 Mix | The Rolling Stones | 5:41 | |
| It's A Hard Rain Gonna Fall | Leon Russell | 5:10 | |
| Lost In The Love Of You | Livingston Taylor | 2:59 | |
| No Hard Feelings | The Avett Brothers | 5:14 | |
| Madman Across The Water | Elton John | 5:57 | |
| Bye Bye Blackbird | Joe Cocker | 3:27 | |
| Ramblin' Man | Allman Brothers Band | 4:48 | |
| Abraham, Martin And John | Dion | 3:20 | |
| Night Moves | Bob Seger | 5:24 | |
| Flying Blind | Sheryl Crow, James Taylor | 3:41 | |
| Carolina In My Mind - Live At The Troubadour / 2007 | Carole King, James Taylor | 4:16 | |
| I Guess That's Why They Call It The Blues | Elton John | 4:45 | |
| End Of The Line | Traveling Wilburys | 3:29 | |
| Walk Away Renee | The Left Banke | 2:44 | |