Mitchell Tenpenny Shares the Story Behind ‘Bigger Mistakes’ [EXCLUSIVE]

Mitchell Tenpenny has a new song, out now. The singer-songwriter just dropped, “Bigger Mistakes,” a tune he wrote alongside Chris DeStefano, Josh Kear, Jeff Braun, and Michael Whitworth, and was inspired by a Carly Simon hit that was released more than 50 years ago.

“I always loved that song, “You’re so vain, you probably think this song is about you,” by Carly Simon,” Tenpenny tells Everything Nash. “My mom used to sing that all the time in the car whenever it would come on Top 40 radio. I don’t know why. She might have had a story that I don’t know about, but I always remember seeing my mom singing that. And when I was going to write that day with my friends, I didn’t have any ideas. That song came on the radio, and it’s like, ‘Man, that’s a cool idea to bring back and talk about.'”

Tenpenny suggested that they write a song that is the opposite of a sad, heartbreak song, and the other writers quickly latched on to the idea.

“I said, ‘What if you wrote a song and said, ‘I’m not worried about you. I’m not playing that game. I’m moving on. I’ve made bigger mistakes than this,'” Tenpenny says with a laugh. “I just wanted to be kind of lighthearted, to help people get over that. I know that that’s a common theme sometimes in breakups. People want to feel like that they’re gonna be remembered more than they are, or thought about. And I think this will be a fun song to say, ‘There are other things more important than this.'”

“Bigger Mistakes” is intended to be a fun, feel-good song, but there is a line in the lyric that references something more serious. Tenpenny sings “My friend Joe Diffie gave me / A bottle of whiskey / Wish we drank it together before he died,” a line that is very true for Tenpenny. Early in his career, when Tenpenny was still touring in a van, he opened for Diffie. The night ended up being a comedy of errors, none of it the fault of Tenpenny or Diffie, but resulted in Tenpenny not being pleased with his performance.

“It was the venue’s fault, but Joe Diffie was the headliner, and he came up to me after the show, just so sorry, and just so apologetic,” the Nashville native recalls. “And it wasn’t his fault at all, but he handed me this bottle of Jack Daniels just to say ‘Man, I’m so sorry.’ We were in a van. We had absolutely nothing. He had no reason to do that. He just handed me this bottle. He’s like, ‘Man, this is all I can offer you. I’m so sorry.’ I was blown away by his kindness and we talked, but I never drank it with him.”

Diffie passed away in 2020 from COVID, but it was important to Tenpenny to honor the country music icon in “Bigger Mistakes.”

“When I was thinking of this song, that story came to me. Obviously, we lost him during COVID, and what a great guy he was to me,” Tenpenny shares. “Just the advice; it was something that I wanted to slip in there to say, ‘Don’t miss out on little opportunities like that,’ without getting too serious.”

Tenpenny is currently serving as the opening act on Jason Aldean‘s Highway Desperado Tour. Find all of Tenpenny’s music and upcoming shows at

Photo Credit: Courtesy of Schmidt Relations / Zach Pigg