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Billy Dean Recalls Doing Music in 90s, Talks Relation To Jimmy Dean

Billy Dean stopped by The Bobby Bones Show for the first time to share stories of playing music in the 90s, if he’s related to Jimmy Dean, perform and more!  

90s country music artist, Dean, known for songs like “Somewhere in My Broken Heart” and “Billy the Kid,” got a call from a bunch of friends saying they heard Bobby Bones talking about him on the radio. He loved to hear the news and thanked Bones for “keeping the old man alive.”  

One of the first things you notice about Dean is his height. At 6’4, he was a great basketball player in High School, but was known more as a singer. His dad was in a country band, and he would play with him at the VFW. He knew his calling in life was to make music when in High School he had six weeks to write a paper about Shakespeare and left it until the last minute and chose to write a song instead. It did well and he figured that’s what he wanted to do for the rest of his life. After High School, Dean left his hometown, Quincy, Florida on a basketball scholarship at a small Mississippi school, while doing music on the side and playing at local bars. Eventually, the pull for music became too strong and he left to go to Nashville and chase his dreams.  

His birth name is Harold Dean, and he was always referred to as Harold growing up. When he came to Nashville, there were no Harold’s making music, so he used his father’s name, Billy and thought it’d be cool for him to see it on Billboards. He’s long been asked if he has any relation to Jimmy Dean. The two met at the ACM Awards years ago and joked about it and even looked into it, but there was no relation. Jimmy wrote Billy Dean a letter at the award show congratulating him and signed it “Love, Dad,” that Billy loved so much he laminated and kept it.  

One of Dean’s biggest hits is “Billy the Kid.” When he first wrote it, he told his co-writer it really reflected what it was like growing up as a kid in the panhandle of Florida and spending most of your time outdoors. He thought it would be too personal to release, and it was the last song choice to put on his second album. To his surprise, he found that people related to it, and it became one of his most well-known songs.  

Dean was on a roll in the 90s making hit after hit, but the country music industry wasn’t sure what to do with him. Around the time his song “Somewhere in My Broken Heart” came out, it crossed over and became a Top 10 Adult Contemporary hit, and country music thought that was his future. Country radio wanted him to pick a lane to stay in, but Dean was just trying to do what was true to his heart.  

Dean now resides in St. George Island in Florida. It’s a small fishing town with a population of 800 people and he called it “nothing fancy.” A few years ago, he went down there and realized the reason he got into music was to make enough money to hopefully own a place there one day. He now lives there to slow down a bit but is grateful that 90s country music is having a renaissance right now. His son, daughter-in-law and grandchild live in Nashville, so he comes back to town often.  

Dean will play 150 shows this year and is working on new music. To learn more, visit While in studio, Dean performed “Billy the Kid” and “We Just Disagree.” Watch below!