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Outlaw Country article

Outlaw Country for Newcomers: Where to Start

Getting into outlaw country is straightforward. The genre is compact, the key records are short and the entry points are clearly signposted. Here is how to begin.

Outlaw Country for Newcomers: Where to Start

Getting into outlaw country is straightforward — the genre is compact, the key records are short and the entry points are clearly signposted. Here is a practical path through the essential material.

Start With the Compilation

The 1976 compilation Wanted! The Outlaws is the best first listen — it covers Willie Nelson, Waylon Jennings, Jessi Colter and Tompall Glaser in a single hour and gives a clear overview of the outlaw country sound. It was the first country album to go platinum, which tells you something about its accessibility. It is available on every major streaming service. Listen once through without skipping; the sequencing is part of the experience. This single album will tell you whether the sound interests you enough to go deeper.

Then Choose Your Path

From the compilation, most listeners split between two paths. If Waylon Jennings' voice and the harder, blues-inflected sound appeals, go to Honky Tonk Heroes (1973) next, then Dreaming My Dreams (1975). If Willie Nelson's more lyrical, acoustic approach resonates, go to Red Headed Stranger (1975). Both albums are under 35 minutes; listen to each twice before moving on. For a breakdown of the key albums, see our albums guide.

Expand to the Songwriters

Once you have the two central artists covered, turn to the songwriters. Kris Kristofferson's debut album (1970) is a foundational text — the songs are extraordinary and the production is minimal. Townes Van Zandt's Live at the Old Quarter, Houston, Texas (1977) is the best single introduction to a writer who influenced every serious outlaw country and Americana artist who followed him. Billy Joe Shaver's Old Five and Dimers Like Me (1973) is essential for understanding the lyric writing that drove Jennings' best records.

Modern Listening

The tradition continues. Tyler Childers' Purgatory (2017) and Sturgill Simpson's Metamodern Sounds in Country Music (2014) are the most critically acclaimed recent records in the same tradition. Cody Jinks and Jason Isbell are both worth knowing. For a full picture of how outlaw country connects to today, see our subgenres guide.

Frequently Asked Questions

How long will it take to work through the essentials?

The core records — Wanted! The Outlaws, Red Headed Stranger, Honky Tonk Heroes, Dreaming My Dreams and Kris Kristofferson's debut — total around four hours of listening. The albums are short by modern standards; most run 30–35 minutes. A focused weekend of listening will cover the essential ground. Following up with the Townes Van Zandt and Billy Joe Shaver records adds another couple of hours.

Is any of this music hard to find?

No. All the major albums are on Spotify, Apple Music and other streaming services. Physical copies are widely available and often cheap — these records sold in large numbers when released and second-hand copies are common. Some of the Townes Van Zandt live recordings have had complicated rights histories, but the main albums are available.

Do I need any background knowledge to appreciate this music?

No prior knowledge of country music is required. The music is direct and accessible — the production is minimal and the lyrics are in plain English. Having some sense of what the Nashville Sound was and why artists rejected it adds context, but it is not necessary for enjoying the records. Our history guide covers the background for anyone who wants it.

What should I listen to after the classics?

Once you have covered the 1970s classics, the natural next step is the progressive country songwriters — Guy Clark, Townes Van Zandt, Billy Joe Shaver — followed by the Americana and No Depression era of the 1990s (Uncle Tupelo, Wilco, Son Volt). From there, contemporary artists like Tyler Childers, Sturgill Simpson and Cody Jinks bring the lineage up to the present. Each stage builds logically on the one before.

About Chloe Nelson

Chloe grew up in London chasing pop's cutting edge across the city's studios and small venues, and got her start writing about the artists her friends hadn't discovered yet. She likes pop made with genuine craft. She writes about pop, production and rising artists.

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