- He got a job at the Nashville Network when he first came to town and would research old footage of country performances. He played bars and worked on demo tracks at night and would give his music to anyone he thought could help him because he was working as a video guy at the time and not really in the music industry.
- He’s a pilot and shared how he would fly to and from shows. Back in 2003, he flew on a private jet with Kenny Chesney and Tim McGraw and they would talk about flying their own planes, so that inspired him to get his pilot's license.
- He once tracked down a music exec in a parking lot to play them his song “What Was I Thinkin?’” He played it on his guitar for them and it got him his first record deal. The song became his first number one single, but he didn’t want that song to be his first single, and instead wanted “Wish It Would Break” to be since it was more country.
Amy shared her favorite Bentley moment was one of the first times he came in and sand “Come a Little Closer,” and included her name in it. Also, Inner Enginering is a book he gave Amy after she adopted her kids. At the time, she wasn’t ready for it and put it away on a bookshelf, and then when her father passed, she picked the book up and it had a lot of what she needed to hear at that moment.
Lunchbox’s favorite moment with him was when he ran into him at the grocery store and saw he forgot his wallet, so he paid for his groceries.
Eddie’s favorite memory of Bentley happened outside the studio when he saw Bentley riding his bike down the sidewalk past the studio.
Bones favorite moment with Bentley was at his Million Dollar Show at The Ryman. Tracy Lawrence was supposed to play, but he got sick, so only six hours before the show, Bentley agreed to fill his spot and performed at the show.
Bones did an interview with Bentley for an hour on his podcast, Bobbycast, you can check out here.