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Stephen Wilson Jr. on Finding Success in the Music Industry in His 40s

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Stephen Wilson Jr. on Finding Success in the Music Industry in His 40s
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When boxer George Foreman claimed the world heavyweight title with a 10th-round knockout of Michael Moorer in November 1994, Stephen Wilson Jr. took note.

Foreman was just five days short of age 46, and Moorer was 20 years his younger in a sport where 30 is deemed “old.” Wilson Jr., 15 at the time, never forgot his dad’s reaction.

“You would have needed a shovel to have scraped his jaw off the floor because he couldn’t believe that a 46-year-old man just became the heavyweight champion of the world,” Wilson Jr. says. “That was probably one of the most impactful events I ever watched in my life. I watched a human defy the odds.”

Wilson Jr., now 46, is defying the odds as well. He won his first Academy of Country Music award when the rough-edged “Cuckoo” claimed video of the year on May 6. His solo performance of “Stand by Me” was one of the highlights of the Country Music Awards last November, and he has a slot on the satellite stage at Nissan Stadium during CMA Fest on June 7. Plus, his quirky “Gary” ranks No. 37 on Billboard’s Country Airplay chart dated May 30.

Wilson Jr., speaking with Billboard Country Update before headlining the Nashville Chapter of the Recording Academy’s annual Block Party May 12, was amused that his pursuit of an artist’s life in his mid-40s is unusual.

Time “only exists because we collectively choose to believe it exists,” he says, presumably drawing on theories from quantum mechanics. “The second we choose to believe it doesn’t exist is the second it becomes non-existent. And so I always had a weird little issue with time.”

If he didn’t know it before, Wilson Jr. became acutely aware that his view of our chronological existence is different once he became a songwriter. After boxing in his Indiana youth, he spent several years as a guitarist in the indie rock band AutoVaughn. He earned a degree in microbiology and chemistry at Middle Tennessee State University in Murfreesboro, Tenn., then worked in research and development for Mars, Inc., but pulled away from the corporate world to become a songwriter in his late-30s. The age thing raised its head at that time, mostly because others had their own weird little issue with time.

“I remember artists being, like, 27 in the writing room with me, and being worried that they were becoming too old,” he says. “They would express their woes to me, like, ‘Oh, I’m getting close to 30 here.’ I’m 37 [at the time], I just quit [my job], I’m just starting my [writing] career. It’s a little awkward, but I don’t tell them that. I just kind of sit there in the room and let them express their grievances.”

Wilson Jr. didn’t plan to go beyond writing songs at that point in his career, but he didn’t plan on the emotional journey that accompanied his father’s death, either. That life passage occurred when he was 39, and it spurred a new phase in his life.

“When my dad died, I died with him,” he says. “Everything that I was — and thought I was — died. And with that came a birth.”

The new Stephen Wilson Jr. was driven to write about the guy that raised him, and he ultimately created a double album, søn of dad, for his first full-sized package with Big Loud. The album is thematically deep, sonically heavy and way beyond anything a run-of-the-mill 27-year-old would dream up in country music. It’s part of what’s appealing about his emergence at this point in his time-defying term on Earth. His rise comes at a creatively ideal time.

“I have more to say at my age now than I did 20 years ago, and I’m a different person than I was 20 years ago,” he says. “I’m not sure if I’d want to hear an album written by me 20 years ago.”

He’s not the first country artist to come of age in the marketplace a few decades after most people come of age. Willie Nelson, one of Wilson Jr.’s icons, was 42 when “Blue Eyes Crying in the Rain” brought him into his commercial sweet spot. K.T. Oslin was 45 when “80’s Ladies” introduced her sly, award-winning voice of experience. Early Grand Ole Opry star Uncle Dave Macon was past 50 when he made his first recordings and debuted on the WSM-AM Nashville show.

One of the benefits that accompanies an artist’s rise in their 40s or beyond is a sense of self that makes them easy to manage.

“Everything is very intentional — what he records, how he records it, the hat that he wears, the style, the clothes that he wears, the guitar that he plays, the sound that that makes, and I just try to stay out of the way,” says his manager, ALJ MGMT owner Alicia Jones. “He knows what he wants to do, and we’re just there as managers to protect it — and not mold it or manufacture it — just to clear obstacles out of the way and support him.”

His grainy vocal style and intense songs caught her attention immediately when she first heard him in 2021; after just a verse and a chorus, she wanted to work with him.

“I met him, and he was so fascinating,” she says. “He’s so smart, you know, and then I got to see him play, and I had absolutely no clue how old he was. Nor did I care.”

His performances don’t necessarily give that away either. His CMA appearance, in which he captivated an entire arena with just his voice and guitar while reinventing “Stand by Me,” displayed a raw urgency. His set at the Recording Academy Block Party was raucous, and he physically owned the stage like a 20-something.

Life as an artist is far more taxing than most fans likely realize. The long hours of travel can lead to dehydration, jet lag, tight muscles and circulation issues. The actual performance, which is only a small part of the day, requires focus, deep breathing and a show of energy — even when the act has little in the tank.

Wilson Jr. still uses boxing exercises to stay in shape for the road. And, of course, neither the concerts nor the lifestyle around it are nearly as depleting — or painful — as going head-to-head with another fighter was when he was pursuing boxing. He’s following a path that few — outside the likes of George Foreman or Willie Nelson — have forged. And he doesn’t intend to turn back.

“I’ve been training for this for a long time,” he says. “I didn’t realize it — like, I’ve always been training hard for something, and now I know what it is. It just took a long time to figure it out.”


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