Episode 506 first aired on June 8, 2016
| Artist | Song |
| Paul Nipper | Texasota – Spring 2016 |
| Paul Nipper | Take A Trip With Me |
| Jacob Jaeger & Ali Holder | Oh So Many Ways |
| Devin White | Don’t Ever Want To Lose You…? |
| John Evans | Waffel House-Free Hashbrowns |
| John Evans | Live From Luckenbach |
| Kalu James | Leave The Light On |
| Craig Marshall | Wouldn’t Be The First Time |
| Betty Soo | Things Are Going To Get Worse |
| Emily Bell | Back To The Way I Was |
| Shane Cooley | Hesitate |
| Migrant Kids | Canvas Of Me |
| Brittany Shane | Pretty In Pink |
| Wild Bill and The Bluebird Specials | Letting You Know |
| David Grissom | Crosscut Saw |