Stephen Wilson Jr. made his Stern Show debut this week, performing his new single “Gary” and a stirring cover of “Stand by Me” live in the studio for a Howard 101 special. The singer, songwriter, and guitarist opened up about his path to music, telling Howard Stern he was once a quiet kid who struggled to find his place before discovering the guitar at 16. That gift from his father shifted everything.
“I was pretty much a fly on the wall, and I really didn’t have much to say,” Wilson Jr. said. “So, it was really hard for anyone to imagine me as a singer because I wasn’t a talker.” He recalled practicing up to 12 hours a day, teaching himself Soundgarden songs and adopting a percussive playing style inspired by Dave Matthews. The dedication helped shape the sound that recently earned him a New Artist of the Year nomination at the 2025 CMA Awards.
During the appearance, Wilson Jr. also shared the story behind his weathered Takamine guitar, nicknamed “One,” which he purchased for $400 from the back of a van in a Nashville parking lot. “I shop with my hands, not brands,” he said with a laugh. He knew within seconds it was the right fit. The performance special airs February 10 at 7 p.m. on Howard 101.