When people think of “Brown Eyed Handsome Man,” the first name that comes to mind is Chuck Berry. Written and released in 1956, it was one of Berry’s most clever and influential songs, blending humor, rhythm, and subtle social commentary into a timeless rock and roll hit. But decades later, another giant of American music — Waylon Jennings — would make the song his own, reimagining it through the lens of outlaw country. His version not only honored Berry’s genius but also revealed Jennings’ gift for taking outside material and stamping it with his unmistakable identity.

Waylon recorded “Brown Eyed Handsome Man” for his 1969 album Singer of Sad Songs. At the time, Jennings was carving out his place in the country world while quietly pushing against the restrictive mold of Nashville’s “countrypolitan” sound. Covering a Chuck Berry tune was, in many ways, a rebellious choice. Rock and country were still viewed as distinct camps, with Nashville producers often frowning on artists who blurred the lines. But Waylon wasn’t interested in fitting into a neat category — he was already laying the groundwork for the outlaw movement that would soon explode.

Musically, Waylon’s version is strikingly different from Berry’s. Where the original had a rollicking, upbeat rock and roll bounce, Jennings slowed the tempo slightly, giving the song a heavier, more deliberate groove. His deep, commanding baritone brought a sense of grit and weight to the playful lyrics. The band behind him leaned on electric guitars, bass, and drums that echoed Berry’s energy but filtered it through a country-rock sensibility. The result was a track that sounded both familiar and refreshingly new, bridging two genres that shared more DNA than Nashville executives liked to admit.

Lyrically, Jennings kept the heart of the song intact. The tale of women falling for a “brown eyed handsome man,” of judges and baseball crowds all bending to his charisma, remained as witty as ever. But sung in Waylon’s voice, the story gained a new dimension. Berry’s version carried sly humor and a sense of youthful rebellion; Jennings’ version felt more weathered, as if the “handsome man” was no longer just a romantic figure, but a rugged outlaw who commanded respect wherever he went.

Critics and fans alike appreciated Jennings’ ability to reinterpret rock and roll classics in his own style. His “Brown Eyed Handsome Man” was praised for showing the deep kinship between rock and country — two genres born from the same Southern soil, shaped by blues, gospel, and folk traditions. Jennings wasn’t just covering Berry; he was affirming that outlaw country could draw from rock’s rebellious energy and still remain authentically country.

Though not released as a major single, the track has endured as a fan favorite and a hidden gem in Waylon’s catalogue. It stands alongside his other covers — from Gordon Lightfoot to Kris Kristofferson — as proof of his versatility and his refusal to be boxed in. More importantly, it’s a reminder that Jennings saw himself as part of a broader American musical tradition, one that included the rhythm and fire of Chuck Berry.

Today, “Brown Eyed Handsome Man” remains a testament to Waylon Jennings’ restless spirit. In his hands, the song wasn’t just a celebration of charm and attraction; it became a nod to the outlaw ethos itself — the magnetic pull of men who live by their own rules, whether in love, in music, or in life. By singing Berry’s words with his own grit and conviction, Jennings didn’t just honor a classic — he expanded its legacy.