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Waylon Jennings’ Shocking Picks for the Best (And Worst) of Country Music
Few artists spoke their mind as boldly as Waylon Jennings. A central figure in the outlaw country movement of the 1970s, Jennings built his reputation on rejecting the rules of Nashville and carving out his own brand of authentic, no-nonsense music. His gravelly voice and unapologetic attitude made him a legend, but it was his honesty—sometimes brutal honesty—that set him apart. When asked about the best and worst of country music, Waylon never held back, and his picks shocked fans and peers alike.
For Waylon, the “best” of country music always came down to authenticity. He often praised fellow outlaws like Willie Nelson, Johnny Cash, and Kris Kristofferson—not just because they were his friends, but because they represented truth in music. These were artists who lived their songs, who wrote from experience, and who refused to bow to industry executives. Waylon admired storytellers like Merle Haggard, whose songs about working-class struggles mirrored the lives of real people. To Jennings, the best of country was never about polish or perfection—it was about grit, honesty, and heart.
But when it came to the “worst,” Jennings could be merciless. He openly criticized the Nashville establishment for churning out formulaic hits designed to sell records rather than tell stories. In interviews, he accused producers and executives of stripping country music of its soul, packaging it into something “safe” and “phony.” Waylon was particularly outspoken about artists who, in his view, sacrificed authenticity for fame. Though he rarely named names directly, his disdain for the highly commercial “countrypolitan” sound of the 1960s and 1970s was clear. Later, he also expressed skepticism toward the flashy, pop-driven country stars who rose to prominence in the 1990s.
One of Waylon’s most shocking statements was his suggestion that some of the genre’s biggest moneymakers were actually harming country music. “If all you care about is record sales, you’re not singing country—you’re selling soap,” he once quipped. Fans who revered mainstream stars were stunned, but others applauded him for defending the integrity of the genre.
Despite his sharp critiques, Waylon’s opinions were never rooted in bitterness. They came from a deep love of country music and a desire to see it remain authentic. He believed that the genre’s greatest strength lay in its ability to connect with ordinary people. That belief drove his own career, from his decision to wrestle creative control away from Nashville producers to his collaborations with The Highwaymen, where he and his peers proved that country could be both rebellious and timeless.
Looking back today, Waylon Jennings’ picks for the best and worst of country music feel prophetic. Many of the artists he championed—Nelson, Cash, Haggard—are celebrated as legends, while the overly polished, manufactured sounds he despised have largely faded. His words continue to resonate as younger generations of musicians fight their own battles between authenticity and commercial pressure.
Waylon’s honesty may have shocked some, but it also preserved a truth at the heart of country music: that the best songs are not just heard—they are lived.
