Introduction
George Strait’s classic heartbreak ballad, “When Did You Stop Loving Me,” was released in April 1993 as the third and final single from his Pure Country soundtrack album. Written by Donny Kees and Monty Holmes and produced alongside Tony Brown, the song reflects Strait’s neotraditional, honky‑tonk roots while delivering a thoughtful narrative of love lost and unanswered questions. It climbed to No. 6 on both the Billboard Hot Country Songs and Canada’s RPM Country Tracks charts .
The song distinguishes itself through its stark, emotive storytelling. Strait’s restrained, poignant vocal delivery drives home the desperation of lyrics pleading, “Darling, when did you stop loving me?” Set to a minimalist arrangement that allows his voice and the lyrics to carry the emotional weight, the track is widely seen as a memorable example of classic country balladry .
A particularly unforgettable moment in the song’s legacy occurred during the closing night of the The Cowboy Rides Away Tour—George Strait’s final touring venture. On June 7, 2014, at AT&T Stadium in Arlington, Texas, he invited Sheryl Crow onstage for a live duet of “When Did You Stop Loving Me.” This high-profile performance paired Strait’s traditional country warmth with Crow’s soulful tone and crossover sensibility, creating a deeply moving rendition that resonated with fans worldwide .
The duet received widespread acclaim. Observers praised the emotional depth and chemistry between the artists, noting how Crow’s harmonies elevated the song to new heights. One article remarked that the performance “is pure country ‘at its best,’” underscoring its significance in the genre .
This live rendition remains one of the most celebrated collaborations in Strait’s storied career—a perfect blend of timeless songwriting and cross‑genre artistry. It stands as a highlight not only of the Cowboy Rides Away tour but of modern country music’s power to unite listeners in emotional connection.