Jesse Keith Whitley thinks about the number 33 often. The singer and son of the legendary Keith Whitley turns 33 in June. His father was 33 years old when he died on May 9, 1989.

Admittedly, their careers took on different trajectories. At 33, the "Don't Close Your Eyes" hitmaker had a couple of No. 1 songs and was synonymous with Ralph Stanley and J.D. Crowe. Jesse Keith is still figuring things out, or at least he was until he started making music for his upcoming studio album.

"When I was younger, 33 seemed so much older," he tells Taste of Country. "What Dad was singing and what he was writing was just so much more than I could comprehend and really understand at that age. They say it’s a 10-year-town. I think it’s a friggin’ 30-year-town.”

The younger Whitley is also a married father, like his father was when he died. So he understands the subtle stresses of trying to raise and protect a family — stresses many men won't talk about. It comes out in the music. "Try to Change My Ways" is an aggressive country-rock song that deviates from anything the name Whitley has ever been attached to, and that's intentional. It's not that Jesse Keith is rebelling, it's that he's finally found his path after years spent following one quietly cleared for him.

"Nobody’s ever heard me this way before this album and this single," he says of the Kirk Roth and Robert Kemp-written song, an in-your-face lyric about protecting American values.

“I love to fish, I love hunting, I love guns. Anything outdoors I’m all about — and of course music — music’s been my story since I was a kid," Whitley says. "I think right now a lot of people are trying to change our ways, and a lot of us don’t want our ways changed."

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While recording and listening to the demo of his song, Jesse Keith started to think of his father. He was driving through the same Kentucky hills Keith Whitley grew up in, on his way to a cousin's funeral, and he started to understand how those hills are his hills, too — an idea that fits with the lyrics of "Try to Change My Ways." For that reason he dedicated the song to his father. He plans to release it on May 9, 2020, the 31st anniversary of Keith Whitley's death.

Jesse Keith wasn't quite two years old when his dad died, but as he hears more stories, he finds he's like him in unexpected ways. Both are musicians, and there's a physical resemblance. They also share a sense of humor.

"I like to mess with people all the time. That’s like my thing,” he tells ToC during a late April phone call. "My dad used to play jokes on people all the time. You know, being a practical joker, sometimes you’re going to scare somebody so bad they’re gonna be a little pissed. Right there makes it all worth it."

It's the differences that fans are going to learn about for the first time in 2020. Jesse Keith is probably not going to replicate Dad's smooth, charming baritone or easy pathos on an upcoming album — expect something more akin to Southern rock — but he's pretty sure his old man would approve if he were here today.

“I think at this point in my life, my dad would say I’m heading down the right path," Jesse Keith Whitley says. "At least, I would like to think that.”

Here Are Keith Whitley's Top 10 Songs

Keith Whitley died on May 9, 1989, but his music lives on. The traditional country singer's smooth baritone-tenor marks his best songs from a half-decade worth of records and many more years' worth of proper romanticizing. Whitley is perhaps more cherished by the current generation of country stars than he was at the time of his death, leading to his induction into the Country Music Hall of Fame as a member of the Class of 2022.

Radio hits, an under-appreciated album cut, a vintage cover song and one fine duet mark this list of the Top 10 Keith Whitley songs.

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