Watch Olivia Rodrigo Sing for Sheryl Crow at Nashville Awards Dinner

Sheryl Crow and Olivia Rodrigo have history. They’ve performed together at Nashville’s Bluebird Cafe, at Crow’s induction into the Rock & Roll Hall of Fame in 2023, and then again in Nashville during a stop on Rodrigo’s headlining arena tour the following year. So, Rodrigo’s appearance in Nashville on Monday night during a dinner honoring Crow’s achievements as a songwriter shouldn’t have come as the biggest surprise.

And yet, in an evening filled with A-level performances by Chris Stapleton, Eric Church, Jason Isbell, Lauren Daigle, and Melissa Etheridge, it was an undeniable showstopper.

Crow, who released her debut album Tuesday Night Music Club in 1993, was the 2026 recipient of the BMI Troubadour Award, an annual honor given out by the performing-rights organization each September in Nashville. Last year, the trophy went to John Fogerty; previous recipients have included Lucinda Williams, John Prine, John Oates, John Hiatt, Robert Earl Keen, and ZZ Top’s Billy Gibbons.

While the star power of both the honoree and those who perform in tribute makes the event a particularly special evening, it’s the intimacy of the dinner that elevates it above other Music City industry parties. On Monday, guests like Maren Morris, Amanda Shires, Jesse Welles, Peter Frampton, Kix Brooks, Nitty Gritty Dirt Band’s Jeff Hanna, and “Choosin’ Texas” co-writer Luke Dick mingled before the performances — and a chicken dinner — got underway.

Isbell went first, delivering a powerful reading of Crow’s “Run, Baby, Run” backed by a house band that included all-stars like Guthrie Trapp on guitar and Nick Buda on drums. Etheridge appeared next, singing a version of “If It Makes You Happy” that earned a standing ovation. Church was an early surprise, putting his own solo, acoustic spin on “Leaving Las Vegas,” before Daigle emerged to bounce her way through “Every Day Is a Winding Road.” It looked like Stapleton would be the closer, as he howled a hard-to-follow cover of “I Shall Believe,” one of four songs performed from Tuesday Night Music Club.

But then Rodrigo was introduced. “What inspires me the most about her is her heart, her kindness, and her generosity… This is my favorite song of hers,” she said of Crow, before launching into the heartrending ballad “Strong Enough.” It was a lilting, faithful interpretation that found Rodrigo singing directly to Crow’s table.

Crow, 64, is in the midst of a career renaissance. She’ll drop a new album, Pick You Up, on Oct. 9, and has emerged as a powerful voice for social causes. Onstage in the BMI lobby in Nashville she veered away from her acceptance speech for a moment to offer her take on a hot-button issue. “Fuck AI,” Crow said. “It’ll never play live.”