Bobby Bones was sent an email asking him to send in a 6-song mixtape playlist highlighting the pivotal moments in his life for a highlight of him. They also asked him to send along a reason behind why each song was chosen. The six songs he chose included Garth Brooks, John Mayer, Hootie & The Blowfish, Beastie Boys, Diamond Rio, and John Anderson.
- "Meet In The Middle" by Diamond Rio -- First ever concert in Hot Springs, Arkansas. The song he waited all song for them to play.
- "Stop This Train" by John Mayer -- The first song that ever spoke to Bobby Bones as a person. Also, his favorite Mayer song ever.
- "Swingin'" by John Anderson -- Bobby Bones Grandma, who raised him, bought this from a gas station and played it every time they left the house.
- "No Sleep Till Brooklyn" by Beastie Boys -- Skinny, dorky, white guys rapping gave him hope for growing up, because he thought they looked like him.
- "If Tomorrow Never Comes" by Garth Brooks -- One of the first CD's Bobby Bones ever bought. It was also the first time Bones could afford Brooks' music.
- "Hold My Hand" by Hootie and The Blowfish -- Darius Rucker was Bobby Bones first ever interview when he was 17 years old, which spawned a friendship 20 years later.