Struggle Jennings's Perseverance Stars In Shoulda, Woulda, Coulda

Struggle Jennings rides a gritty guitar stomp as he sings his story of perseverance in "Shoulda Woulda Coulda," his new single.

The song — available first to Taste of Country readers during this exclusive premiere — is the newest from El Camino, Jennings' next album. The fall 2023 release also promises collaborations with Jelly Roll, JD Huggins, Caitlynne Curtis, Bonnie Stewart and Jennings' daughter, Brianna Harness.

"I came too far to let go now / Nothing to prove, got a lot to show now," the Nashville-based rapper-turned-country-singer professes.

Much like his friend and touring partner Jelly Roll, he's being sincere when he says:

"All them woulda shouldas can’t never coulda done what I did / Been where I’ve been / Shoulda woulda coulda / Climb that hill fell down came back again / shoulda woulda coulda never done what I did / Shoulda woulda coulda."

Angels and Outlaws

Jennings — grandson of Waylon Jennings and Jessi Colter — is currently on Jelly Roll's Backroad Baptism Tour. The two men have a similar history: A troubled life as a teen and young adult landed him in prison, where he began to focus on songwriting and music.

“I was a drug dealer for a long time, and I felt like I didn’t really have a victim," Jennings told Taste of Country earlier this year. "I didn’t feel like I was out there hurting anybody. I was trying to justify that I was doing it for my kids. In the end, they (seven of them total) became the victims.”

The "Shoulda Woulda Coulda" lyrics seem to refer to those experiences. Specifically, he's calling out doubters in a rock and hip-hop influenced lyric, mixed with blues and country instruments.

The El Camino album is the follow-up to Monte Carlo, also released in 2023.