When Country Outlaws Collide: Travis Tritt & Waylon Jennings’ Unforgettable Duet at the Grand Ole Opry

Travis Tritt burst onto the country music scene in 1989, joining what’s now called the legendary “Class of ’89.” But while many of his peers leaned into a more traditional country sound, Tritt carved a different path—a rebellious, outlaw edge that set him apart from the start. It wasn’t just an image—it was who he was. And it paid off. With seven Platinum-certified albums, Tritt would go on to become one of the most successful artists in country music history.

It didn’t hurt that he had one of the best mentors any country artist could ask for—Waylon Jennings. Early in his career, Tritt crossed paths with the outlaw legend, and the two hit it off instantly. Their connection quickly grew into a genuine friendship rooted in mutual respect, and Tritt never shied away from expressing his admiration for the man who helped redefine country music.

A Duet for the Ages: “Where Corn Don’t Grow” (Grand Ole Opry, 1997)

Their bond was captured in a powerful moment on the Grand Ole Opry stage in 1997, when Jennings and Tritt teamed up for a spine-tingling duet of “Where Corn Don’t Grow.”

Both men had recorded the song individually—Jennings first in 1990 for his album The Eagle, where it reached #67 on the Billboard Hot Country Songs chart. Then Tritt released his version in 1996, and it shot up to #6, becoming a fan favorite.

Although they never recorded a studio duet together, this live performance is the next best thing—and it’s unforgettable.

With Steve Wariner playing guitar, Jennings and Tritt began by trading verses, each bringing his own grit and soul to the story of chasing dreams beyond the family farm. But when their voices finally joined together? Pure magic.

You could feel the electric energy, the mutual admiration, and the shared outlaw spirit in every note. Their chemistry was undeniable, and the performance was nothing short of chill-inducing perfection.

This duet is more than just a performance—it’s a piece of country music history, a moment when two generations of outlaws stood side by side, honoring the genre they both helped shape in their own way.