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Outlaw Country roundup

The Best Outlaw Country Songs Right Now

The essential outlaw country tracks are not greatest hits in the commercial sense. They are moments where the music's values of independence, honesty and craft converge.

The Best Outlaw Country Songs Right Now

The best outlaw country songs are not greatest hits in the commercial sense — they are statements of artistic intent, moments where the music's values of independence, honesty and craft converge. Here are the essential tracks.

Waymore's Blues — Waylon Jennings (1975)

A stripped blues-country track recorded with Jennings' own band, "Waymore's Blues" is as direct a statement of the genre's values as any song on record. The arrangement is minimal — guitar, bass, drums — and Jennings' vocal is conversational rather than operatic. It appeared on Dreaming My Dreams and became a signature live track. It demonstrates what the movement sounded like when it was most confident in itself.

Luckenbach, Texas (Back to the Basics of Love) — Waylon Jennings (1977)

Recorded for Ol' Waylon, this track became the movement's most commercially successful single and its most explicit lyrical statement — a song about escaping Nashville's commercial pressures by returning to small-town Texas simplicity. It reached number one on the country charts and brought outlaw country to its widest audience. The irony of a rejection-of-commercialism anthem becoming a massive commercial hit was not lost on the artists involved.

Blue Eyes Crying in the Rain — Willie Nelson (1975)

Nelson's recording of Fred Rose's 1945 song on Red Headed Stranger is the album's most famous track. Its simplicity — one voice, one guitar — made it a number one hit and demonstrated that outlaw country could achieve mainstream success without any concessions to the Nashville Sound's production conventions. Nelson's phrasing, with its characteristic behind-the-beat timing, is unmistakable. See our albums guide for more on the record.

Sunday Mornin' Comin' Down — Kris Kristofferson

Kristofferson's song about waking up alone after a night of drinking is one of the outlaw country movement's central texts. Johnny Cash performed it on his television show in 1970, reading the unexpurgated lyrics on live television despite network objections. Kristofferson's version is definitive, but Cash's recording brought the song to a vast audience. Its literary frankness about alcoholism and loneliness set the tone for the kind of honest writing the movement valued. For a guide to the key artists, see our artist guide.

Frequently Asked Questions

Are there more recent songs in this tradition worth knowing?

Yes. Sturgill Simpson's 'Turtles All the Way Down' and Tyler Childers' 'Feathered Indians' are contemporary tracks that fit the same tradition — honest writing, stripped production, refusal of mainstream country's conventions. Jason Isbell's 'Cover Me Up' and Cody Jinks' 'I'm Not the Devil' are also worth knowing. The lineage is continuous.

Which Kris Kristofferson song is most important?

Sunday Mornin' Comin' Down is the most historically significant — its performance on the Johnny Cash TV show in 1970 was a landmark moment for honest lyric writing in country music. 'Me and Bobby McGee' (recorded by Janis Joplin and Roger Miller, among many others) is more widely known. Both are essential Kristofferson compositions.

What makes these songs different from mainstream country of the time?

The lyrics engage with failure, loneliness, alcoholism and mortality without the redemptive or humorous framing that mainstream country often applied to difficult subjects. The production is minimal — no string arrangements, no background choirs. The songs were often written by the artist performing them, which was unusual in a Nashville system that relied heavily on professional songwriters and session musicians.

Did any of these songs cross over to pop audiences?

Several did. Janis Joplin's recording of 'Me and Bobby McGee' reached number one on the pop charts in 1971. 'Blue Eyes Crying in the Rain' crossed over significantly. The artists involved were generally uninterested in pop crossover as a goal, but the songs were strong enough to reach audiences beyond country radio.

About Olivia Parker

Olivia was raised in Liverpool, a city that treats its musical past as a living thing, and grew up assuming everyone's hometown had shaped pop history. She's fascinated by how great songs are actually written and what makes them last. She covers songwriting, pop history and the artists behind the hits.

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