Everybody loves Willie Nelson. However, even the biggest fan would be hard-pressed to be familiar with his entire discography. He had released 104 studio albums and 14 live albums over the years. So, to say that listening to his entire discography is a daunting task would be an understatement. That didn’t stop me from trying–and failing–to do it, though.
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I realized early on that I likely wouldn’t get through Nelson’s discography in a mere seven days and give each song the attention it deserved. So, I came up with a system. I chose to ignore the big albums like Red Headed Stranger, Phases and Stages, and his duet LPs with Waylon Jennings and Merle Haggard. Then, I used a random number generator to guide me through the rest. After days of great records, I found seven deep cuts that I think need more attention.
“Cowboys Are Frequently Secretly Fond of Each Other”–Lost Highway (2006)
Willie Nelson and Orville Peck cut a version of this Ned Sublette-penned satirical tune in 2024. However, he released a solo rendition of it back in 2006 on Lost Highway. It’s more than an entertaining and thought-provoking track. It was also the first LGBTQ+-themed song from a mainstream country artist.
“Crazy”–And Then I Wrote (1962)
When most people think of “Crazy,” they think of Patsy Cline. She took the song to No. 2 in 1961, and it became one of her signature tunes. It also bolstered Willie Nelson’s songwriting career. While this is far from a deep cut in the overall country music world, few people talk about the version that appeared on Nelson’s debut album.
“London”–Words Don’t Fit the Picture (1972)
Words Don’t Fit the Picture was one of Willie Nelson’s first albums to move away from the Nashville Sound. Working with producer Felton Jarvis, he got a little closer to what would become his signature sound after the release of Red Headed Stranger. “London,” in my opinion, is a rock-solid example of that style. From the spoken-word intro to the sparse, bluesy guitar work, this is one that will stick with me for a while.
“Have I Told You Lately That I Love You”–Make Way for Willie Nelson (1967)
Nelson is a great songwriter, but I also love his covers. His guitar style, arrangements, and vocal delivery make his versions of even well-worn songs seem fresh. His version of “Have I Told You Lately That I Love You” is a standout example of his knack for interpretation. The song has been recorded by countless artists, including Elvis Presley, Eddie Cochran, Bing Crosby, Bob Hope, and Jim Reeves, but Nelson owns it.
“A Little Old Fashioned Karma”–Tougher Than Leather (1983)
The fact that this song is a deep cut is a crying shame. The western swing-style fiddle and Willie Nelson’s lyrics about someone getting what they deserve made me back this song up and listen to it again. The line of guitar and piano solos in the middle of the song made me add it to my personal playlist.
“Hello Walls”–Funny How Time Slips Away (with Faron Young) (1986)
Faron Young brought Willie Nelson his first major hit as a songwriter when he took “Hello Walls” to the top of the country charts for nine weeks in 1961. It’s a fantastic song, and hearing them sing it together makes it that much better.
“Heartaches by the Number”–For the Good Times: A Tribute to Ray Price (2016)
Penned by the legendary Harlan Howard, “Heartaches by the Number” is by far my favorite Ray Price song. Willie Nelson did a phenomenal version of it on his 2016 tribute to Price. The Time Jumpers, which at the time featured Vince Gill, backed him on the song and gave it a beautiful classic country feel, complete with plenty of fiddle and pedal steel.
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