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Tell Me When It’s Over—but with a performance this powerful, no one wanted it to end. Sheryl Crow, at 60, stepped onto the CMT Crossroads stage like time had never touched her. That voice? Still smooth, still effortless, still carrying the same magic it did decades ago. And then there was Chris Stapleton—gritty, soulful, and as always, the kind of musician who doesn’t need the spotlight to shine. He let their voices dance together, his rich, whiskey-warm tones melting into hers like they were made for each other.

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March 26, 2025

In September 2019, Sheryl Crow and Chris Stapleton delivered a powerful performance of “Tell Me When It’s Over” on CMT Crossroads: Sheryl Crow & Friends. This collaboration showcased the seamless blend of Crow’s versatile artistry and Stapleton’s soulful country vocals, bringing the song’s emotional depth to life.

“Tell Me When It’s Over” is a track from Crow’s 2019 album, Threads, which features collaborations with various esteemed artists. The song delves into the complexities of a tumultuous relationship, with both artists delivering heartfelt performances that resonate with listeners.

The CMT Crossroads episode, which aired on September 27, 2019, celebrated Crow’s musical journey by pairing her with artists like Stapleton, Jason Isbell, Joe Walsh, Emmylou Harris, Bonnie Raitt, and Lucius. The special included intimate performances and interviews, offering fans a unique glimpse into Crow’s collaborative spirit and the stories behind the music.

The chemistry between Crow and Stapleton during “Tell Me When It’s Over” was palpable, with their voices intertwining effortlessly to convey the song’s raw emotion. This performance not only highlighted their individual talents but also underscored the power of collaboration in creating memorable musical moments.

For those who wish to experience this remarkable performance, you can watch it below:

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