VIDEO: Stephen Wilson Jr. Performs ‘Gary’ and Covers ‘Stand by Me’ in Stern Show Debut
Rising rock and country music star records a Howard 101 concert special live in the Stern Show studio
February 10, 2026
Singer, songwriter, and guitarist Stephen Wilson Jr. never expected to become a famous musician. Making his Stern Show debut Tuesday morning to record a Howard 101 special and perform his new hit “Gary” live for Howard and his listeners, the rising rock and country music star admitted he’d been a quiet child struggling to find his place in the world before first picking up the guitar.
“I was pretty much a fly on the wall, and I really didn’t have much to say. So, It was really hard for anyone to imagine me as a singer because I wasn’t a talker,” Stephen told Howard.
But everything changed at the age of 16 when his father gifted him a guitar.
“I was really trying to figure out, like, am I good at anything? I thought I was just kind of gonna be a [science] nerd for the rest of my life, and I was totally fine with that,” Stephen said, adding, “But when I started playing guitar it was like I’ve always known how to do these things. It almost makes me believe in past lives.”
Wilson Jr. recalled practicing up to 12 hours a day, teaching himself Soundgarden tunes (and tunings) while also learning how to play his acoustic guitar with a percussive mindset — “like a drum with strings” — just like Dave Matthews, one of his biggest musical influences.
All his practice eventually paid off, of course, in the form of a New Artist of the Year nomination at the 2025 CMA Awards, a growing legion of fans champing at the bit to catch his next tour, and his haunting, critically acclaimed new track “Gary.”
Howard was excited for his guest to perform “Gary” — as well as his iconic “Stand by Me” cover — but first he needed to know more about the battle-worn guitar Stephen had brought with him, which reminded Howard of Willie Nelson’s legendary guitar “Trigger.”
“I shop with my hands, not brands,” Stephen said with a laugh, explaining he’d found his weathered Takamine guitar — dubbed “One” — on Craigslist and purchased it for $400 in a Nashville parking lot.
“This dude sold it to me out of the back of his van. He had an amplifier that he plugged into a cigarette lighter,” Wilson Jr. continued. “I plugged it in, and I knew within like five seconds that this was my forever guitar.”
Listen to Howard Stern Presents: Stephen Wilson Jr. on Friday, Feb. 10 at 7 p.m. on Howard 101 and get more information on the singer-songwriter’s upcoming tour dates here.
