3 Country Songs That Secretly Influenced 1990s Americana

These incredible country songs had a hand in inspiring Americana musicians, as well as the subgenre's boom, in the 1990s.

Apr. 5, 2026 at 4:21pm

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Country and Americana occupy two sides of the same coin, but the latter's boom in the 1990s would not have happened if it weren't for country music that came before. This article looks at three classic country songs that heavily inspired 1990s Americana and alternative country tunes, including 'Pancho and Lefty' by Townes Van Zandt, 'Are You Sure Hank Done It This Way' by Waylon Jennings, and 'Desperados Waiting For A Train' by The Highwaymen.

Why it matters

The influence of these iconic country songs on the 1990s Americana movement highlights the deep connections between the two genres. Outlaw country's DIY ethos and narrative-driven storytelling were key inspirations for the emerging Americana scene, helping to shape its sound and attitude.

The details

Townes Van Zandt's 'Pancho and Lefty' not only inspired the plainspoken, narrative-driven songwriting of 1990s Americana artists, but it also went on to be covered by country legends Willie Nelson and Merle Haggard years later. Waylon Jennings' 'Are You Sure Hank Done It This Way' exemplified the outlaw country sound that influenced the punk rock attitude of 1990s alt-country bands like Uncle Tupelo and The Waco Brothers. 'Desperados Waiting For A Train' by The Highwaymen, a supergroup of country and Americana greats, was a roots revival track that also left its mark on the 90s Americana boom.

  • Townes Van Zandt released 'Pancho and Lefty' in 1972.
  • Waylon Jennings released 'Are You Sure Hank Done It This Way' in 1975.
  • The Highwaymen released 'Desperados Waiting For A Train' in 1985.

The players

Townes Van Zandt

A legendary country singer-songwriter whose plainspoken, narrative-driven style influenced many 1990s Americana artists.

Waylon Jennings

An outlaw country pioneer whose rebellious sound and attitude inspired the punk rock ethos of 1990s alt-country bands.

The Highwaymen

A supergroup of country and Americana greats, including Johnny Cash, Kris Kristofferson, Willie Nelson, and Waylon Jennings, whose 'Desperados Waiting For A Train' was a roots revival track that impacted the 1990s Americana boom.

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What they’re saying

“Not only did this Townes Van Zandt classic inspire their plainspoken, narrative-driven storytelling in songwriting that 1990s Americana artists leaned into, but 'Pancho and Lefty' also inspired country musicians in the decades after it was released.”

— Em Casalena, Author

“Outlaw country and late 20th-century Americana go hand-in-hand. Outlaw country was, in a way, a very punk rock response to the polished status quo of Nashville country music. Likewise, Americana and alt-country music in the 1990s, notably from Uncle Tupelo and The Waco Brothers, had a DIY ethos and attitude that was not unlike outlaw country music.”

— Em Casalena, Author

“Considering that the supergroup was made up of the finest country and Americana had to offer, I'm not surprised this song was so influential among musicians in the 90s.”

— Em Casalena, Author

The takeaway

The enduring influence of these classic country songs on the 1990s Americana movement underscores the deep connections between the two genres. The plainspoken storytelling, outlaw attitude, and roots revival sound of these country tracks helped shape the emerging Americana scene, inspiring a new generation of musicians to carry on the tradition.