Jackson Dean has toured with Lainey Wilson, but he has also become close friends with the superstar. Dean was fortunate enough to open for Wilson on both her Country’s Cool Again Tour, as well as her international Lainey Wilson: LIVE Tour. But before she was his tour boss, she was Dean’s good friend, who has taught the rising star plenty over the years.
“One thing I’ve always admired about Lainey, that I saw even from what we met years ago, is just how gracious she is,” Dean reveals. “And just how she handles herself around people, everybody, just people in general. Me being a young man myself, I can get right hot-blooded sometimes, and I’ve never once seen her — I’ve seen her stressed, but I’ve never seen her once cross She’s definitely led by example. In an industry where nerves can really get the best of you, she’s got ice water in her veins.”
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Dean may not have the success that Wilson has, at least not yet, but he’s well on his way. The 24-year-old has a Top 25 hit with “Heavens to Betsy.” The song, from his sophomore On The Back Of My Dreams record, was written by Dean, along with Benjy Davis, and Driver Williams, about a father who is in Heaven, trying to communicate with his daughter, Betsy, via CB radio.
The song says in part, “Heavens to Betsy / I don’t know if you can hear me / Up here you’re coming in clear as a bell / Heavens to Betsy / I finally quit the drinking /’Cause I hate that my demons put you through hell.”
“Both of my best friends growing up slept on my couch for probably two years, on and off,” Dean tells Billboard. “I remember Dylan’s dad never being in the picture until we were 16, 17 years old, so I had that little bit of connection with it. And I’ve seen so many situations like that.”
Dean had no idea when he released the song that it would quickly become the most impactful song of his career, and not just based on chart success or airplay.
“I was at a show one time, and I can’t remember where it was,” Dean remembers. “But I had this guy come up to me and he grabs me by the shoulder, and I was like, ‘Hey man, what’s up?’ And he goes, ‘There’s a couple of your songs that changed my life, man. I thought about ending it, and you pulled me back from the dark.’ And that was the first time I was like, ‘Wow.’ And then it happened again, and then again. And I was like, ‘All rlright, I guess I’m doing something right.”
Dean is spending much of 2025 on the road, including his headlining the UK leg of his On The Back Of My Dreams Tour. Find all of Dean’s music and upcoming shows at JacksonDeanMusic.com.