Willie Nelson has had a very long and successful career. Throughout that career, he has experimented with everything from country blues to gospel to even reggae here and there. But at the heart of what made him famous, outlaw country is still Willie Nelson’s claim to fame.
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1. “The Harder They Come”
This 2005 track comes from Willie Nelson’s iconic reggae-country crossover album. At the time, Countryman was considered a flop. However, it’s since become a bit of a cult classic.
Instead of staying within the rigid confines of what people believed outlaw country was all about, Nelson decided to do the most outlaw thing ever: Make a country album with reggae and gospel elements, without much concern for what people thought. “The Harder They Come” is a standout track from that record.
2. “Pancho And Lefty”
Willie Nelson’s outlaw country hits include songs like “Blue Eyes Crying In The Rain” and “On The Road Again”. However, “Pancho And Lefty” is another song that gave Nelson (and friend/collaborator Merle Haggard) a pretty hefty career boost.
Their cover of this famous Townes Van Zandt song came out in the early 1980s during a period when outlaw country had more or less faded into musical obscurity. This dynamic duo brought it back into fashion and hit no. 1 on the country charts.
3. “Mammas Don’t Let Your Babies Grow Up To Be Cowboys”
This is another stunning rendition of a song written by someone else that Willie Nelson breathed new life into. Nelson and fellow outlaw Waylon Jennings covered “Mammas Don’t Let Your Babies Grow Up To Be Cowboys” by Patsy and Ed Bruce for their 1978 duet album. It’s a gorgeous piece of work that became a staple song for use in Western films like The Electric Horseman.
4. “Highwayman”
Another reason why Willie Nelson is the king (or at least, one of a few kings) of outlaw country was his ability to seamlessly fit into the supergroup of other outlaw country icons, The Highwaymen. This outfit was composed of all the greats, including Nelson, Johnny Cash, Waylon Jennings, and Kris Kristofferson.
The song “Highwayman” was originally a Jimmy Webb tune. It inspired not only the namesake of Nelson’s supergroup but also their debut album and their cover version of “Highwayman”.
Photo by Tom Hill/WireImage
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