Four years ago, Tyler Perry’s stepfather offered him a job at his dog-training company in Portsmouth, Rhode Island. At the time, Perry had little else going on—he was 29, living in his mother’s basement, unsure what to do with his life.
In 2017, he had dropped out of Berklee College of Music, where he was supposed to be studying songwriting but mostly skipped class and smoked weed. The songs he wrote back then were introspective and folk-inspired, influenced by artists like Nick Drake and Elliott Smith—musicians he’d discovered in high school, just as depression first took hold. “I was depressed for, like, 10 years,” he admits.
During slow hours at the office, he’d browse Craigslist, daydreaming about moving to New York, Nashville, or LA. On a whim, he applied for a recruitment job at a commercial real estate company in Los Angeles, lying about his experience and lack of a degree. “I just wrote a really good email,” he says. “Twenty minutes later, they called me. I did two interviews in one day, and then they asked, ‘Can you be here in two weeks?’”
Perry had never even been to LA. That night, he talked it over with family and friends. His mom told him, “What do you have to lose? A few thousand dollars? You can always come back.” So he packed up and moved to Venice Beach.
Last fall, a clip of Perry performing his song Help Me Out at The Fable, a bar in Eagle Rock, started circulating online. The song—a plea for self-acceptance, delivered with the same longing as a love ballad—showcased his magnetic stage presence. Dressed in triple denim, he moved with effortless grace, his voice shifting from deep and earthy to soaring highs. There were echoes of Elvis, Roy Orbison, and Harry Nilsson in his performance—something magical and effortless.
In person, though, Perry is quieter, more introspective. Sitting in a Brighton café between sets at the Great Escape festival, he speaks softly, jumping from Rhode Island suburbs to WeWork’s free kombucha to philosopher Alan Watts’ musings on ego. It’s clear there’s a gap between the confident performer onstage and the more hesitant man across the table.
Before the dog-training job, before the real estate gamble, Perry had started working with a counselor and dietitian named Courtney Huard. For two years, they focused on improving his body image and mental health—a turning point for him. “She was incredible, and I’m lucky I found her,” he says. Around the same time, he discovered self-help teacher Eckhart Tolle’s The Power of Now and took an Enneagram personality test. “I pinned my personality to a wall and saw it clearly for the first time,” he recalls. “It shocked me out of depression. I had this spiritual awakening.”
The problem was, this new version of Perry didn’t fit with his old catalog of melancholy folk songs. For years, he’d hidden behind his guitar onstage, singing in a flat whisper, trying to be “cool” in a detached, mysterious way. “But that’s not really me,” he admits.
In LA, he lived out of a suitcase—working at the real estate office by day and playing open mics at night. He’d usually perform a couple of his own songs before ending with Roy Orbison’s Crying. That last song always brought the house down. “People would freak out like it was my birthday,” he says. “Everyone looking at me, clapping.”
It was then he realized—covering Orbison’s music unlocked something in him.The song drew on skills Perry first learned in high school musical theater—a strong singing voice and a sense of warmth and showmanship. He wondered if this could be a new path for him, blending all his musical influences, from show tunes to Fleet Foxes, with nods to Jonathan Richman and The Who’s 1969 rock opera Tommy. He created a character for himself named Tyler Ballgame—a playful reference to Boston Red Sox legend Ted Williams’ nickname, “The Kid,” while also poking fun at his own past, having wasted years of potential in his mother’s basement, far from any sports glory. He began imagining how this character would write and perform.
At Berklee, Perry had taken a performance class taught by Livingston Taylor (brother of James Taylor). The sessions were held in a theater, and on the first day, Taylor had each of the 40 students stand on stage, palms outstretched to the audience, shifting their weight in rhythm while making eye contact. Perry found the exercise brilliant.
Years later in Los Angeles, he remembered that lesson—it felt like an act of radical presence, something Tyler Ballgame would do. He started incorporating it into his live shows. “I’d reach out to the crowd, look them in the eye, like we’re here to share this moment,” he said. “I’m trying to connect, and we’re going to experience this together.” The songs flowed effortlessly—soulful, sometimes sad, but always carrying a spark of hope. They had the timeless quality of classics.
Perry moved to East Los Angeles, collaborating with local musicians and playing live as much as possible. One day, producer Jonathan Rado (known for his work with Miley Cyrus and The Killers) saw an Instagram story of a Tyler Ballgame show and reached out. Perry visited Rado’s studio soon after, and within weeks, they’d recorded enough material for an album.
Word spread quickly, and by last fall, record labels were competing to sign him. He ultimately chose British indie label Rough Trade, bonding over a shared love of Nick Drake and Arthur Russell. “I had a lot of options—it was flattering and surreal,” he said. “But I kept coming back to Rough Trade because they already love the kind of music I naturally make. They’ve released all the music I adore.”
Perry is easygoing in conversation, and after an hour and a half, I ask if there’s anything else he’d like to share. He hesitates. “Maybe I should mention my counselor, Courtney, again,” he says quietly. “She was killed—horrifically.” Courtney Huard had been murdered by her husband, who later took his own life. Perry found out when a friend sent him a news article from their hometown in Rhode Island. Seeing her photo left him stunned.
At the time, he’d been writing Help Me Out, a song largely inspired by her. “She helped me see that my worth wasn’t tied to my body or how others saw me—things that had once kept me offstage entirely,” he said. “So many people in her funeral posts and obituary wrote, ‘She set me on my path.’ She was special. It just shows how fragile life is. So now, I live for her.”
It’s a hot afternoon, but Perry takes the stage at UnBarred Brewery wearing a wool sweater. He looks out at the crowd, spreads his palms gently, and begins to sing. The performance is golden—the songs feel like they’ve always existed, and Perry is completely mesmerizing.As he plays, I remember something he mentioned during lunch—about the freedom and spontaneity of performing. “I want to be completely in the flow, lost in the moment,” he said. “Where nothing feels rehearsed or forced.”
Some shows, he explained, just click—when the band connects, the audience feels it too. “That’s when it becomes real magic. A celebration of the joy of playing music.” Today, as Perry and the band perform, the air hums with that same joy—something truly magical on this warm Sussex afternoon.
Tyler Ballgame’s new single, New Car, is out now. Catch him at the End of the Road festival near Blandford Forum on August 30th and at The Lexington in London on September 10th.
