4 Revered Outlaw Country Legends Who Never Had a No. 1 Hit

Outlaw country spawned countless incredible musicians, from Merle Haggard to Waylon Jennings to Willie Nelson. Unfortunately, many bands and individual musicians from the golden era of outlaw country never saw much success commercially, despite penning some of the finest songs of their generation. Let’s look at some revered outlaw country musicians who never had a no. 1 hit!

1. Tompall Glaser

Tompall Glaser never had a no. 1 hit of his own, unfortunately. However, his highest-charting song was “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” with the Glaser Brothers, which hit no. 2 on the country charts. That being said, he was an indispensable figure in outlaw country music. 

Glaser helped to produce Waylon Jennings’ famed 1973 record Honky Tonk Heroes. He penned a number of incredible songs through the years, and worked with everyone from Jessi Colter to Patsy Cline to Willie Nelson.

2. Jerry Jeff Walker

Out of all the outlaw country musicians who never had a no. 1 hit, this one is shocking. Jerry Jeff Walker penned the famous song “Mr. Bojangles”, which only made it to no. 77 on the Billboard Hot 100. 

It’s wild to think that Walker didn’t experience substantial commercial fame; that song alone from 1968 has been recorded by icons like Bob Dylan, Neil Diamond, and John Denver.

3. Billy Joe Shaver

Billy Joe Shaver is one of the most respected figures in outlaw country music, but he somehow never got a no. 1 hit. Icons like Kris Kristofferson and Bob Dylan have praised the late singer/songwriter for his contributions. Some of his songs were even recorded by Johnny Cash, Elvis Presley, and more. And he did it all without two of his fingers! 

Unfortunately, Shaver’s highest-charting single was the 1977 tune “You Asked Me To”, which only made it to no. 80 on the Hot Country Songs chart.

4. Townes Van Zandt

Townes Van Zandt penned countless hits in the outlaw country music genre, but he never saw a no. 1 hit himself. It’s a real shame. But thankfully, Zandt has since been immortalized in country music as a well-respected icon. 

Willie Nelson and Merle Haggard famously covered his song “Pancho And Lefty”. That version quickly shot to no. 1 on the Billboard country charts back in 1983. So, technically, he did have a no. 1 hit as a songwriter, but not as a performer.

Photo by Rick Diamond/Shutterstock

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