“I Owed It to Myself, but I Also Owe It to Him”: The Tragedy That Sent Lainey Wilson Into One of the Darkest Seasons of Her Life

Lainey Wilson is opening up about a challenging time. The country singer recently took to Instagram to share a clip from her Netflix documentary, Lainey Wilson: Keepin’ Country Cool.

In the clip, Wilson spoke about Jerry Cupit, a pal of her grandfather’s who helped her out early on in her career. Cupit died in 2014 at age 60.

“We realized, oh no, this is not good. That’s when I knew that he’s probably not gonna make it much longer,” Wilson said in the clip. “He told me, he said, ‘I want you to keep going.’ And then he passed away.”

After Cupit’s death, Wilson said she “felt lost, and lonely, and scared, and it was a very, honestly, a dark season of my life.”

“I didn’t know which way to go. I didn’t know who to turn to, but I still knew that this was my calling. And I knew that I wasn’t gonna pack it up and go home,” she said. “I knew that I needed to stick it out. I honestly kind of felt like I owed it to myself, but I also owe it to him.”

The clip continued with Wilson showing off the binder full of recommendations she used to ask people, including Cupit, to write for her.

“Lainey is a complete package. She sings, writes, and will be a video superstar,” Cupit’s letter read. “Her talent will demand a place in the ranks of the major country music platform.”

After she re-read Cupit’s recommendation, Wilson remarked, “That’s pretty cool. He spoke it.”

In the caption, Wilson wrote, “Jerry helped me find my way in Nashville. I carry a little piece of him with me every time I write.”

What Lainey Wilson Has Shared About Jerry Cupit

Back in 2021 during an appearance on the Just Being ERNEST podcast, Wilson opened up about Cupit’s role in her life.

“When I first moved here, I really didn’t know a whole lot of people. I wasn’t old enough to anywhere, do anything. I was 19,” Wilson said. “So there was a guy from my hometown—his name was Jerry Cupit—he had some success in the ’90s with like Ken Mellons, Kevin Sharpe.”

Wilson went on to share that, back in the ’70s, her grandfather “gave Jerry Cupit a few hundred bucks to help him move to Nashville and get started.” Decades later, Cupit returned the favor.

“As a favor in return, Jerry let me live in his studio parking lot for free for those three years. So he was really my only contact that I knew,” she said. “He’s really the one that taught me how to write a song. We would write every day. We did that for a few years, and then he got sick and passed away. At that point, I didn’t really know anybody except for him, and I really had to kind of start over.”

Photo by Taylor Hill/FilmMagic

The post “I Owed It to Myself, but I Also Owe It to Him”: The Tragedy That Sent Lainey Wilson Into One of the Darkest Seasons of Her Life appeared first on American Songwriter.