Few country artists alive today are as legendary as Willie Nelson. He was a major player in the outlaw country music movement. His live performances are still as wondrous today as they were in his early years. And, considering the man has over 100 albums in his discography, I think it’s safe to assume that even diehard Willie Nelson fans haven’t heard every single one of his deep cuts. Let’s take a look at just a few, shall we?

“Rainbow Connection” from ‘Rainbow Connection’ (2001)

This title track from Willie Nelson’s 49th studio album of the same name is a great example of what the man was doing decades into his career at the very start of the 21st century. Where other artists might have struggled to keep up with the times, Nelson just kept on making music like it was easy. The whole of this album is great (it earned a Grammy nom, after all). But, that cover of a Muppets tune is the most fun thing on the record.

“Hello Walls” from ‘Hello Walls’ (1961)

You might be thinking: That is definitely not Willie Nelson. You would be correct. “Hello Walls” was first recorded by Faron Young in 1961, but the song itself was written by Willie Nelson. In fact, this No. 1 Country tune was the song that introduced Nelson to the music world on a national level! Nelson would later record a more rock-leaning version of this song with The Reverend Horton Heat, specifically on the album Twisted Willie from 1996.

“Half A Man” from ‘Here’s Willie Nelson’ (1963)

Back in the early 1960s, Willie Nelson had not yet quite gotten into his outlaw country phase. And yet, his music was still inspiring and had just a glimmer of what he would embody later on in his career. “Half A Man” is a fine little oldie from 1963, and it also did quite well via sales and the charts. The tune peaked at No. 25 on the Billboard Hot Country Singles chart.

“I’d Have To Be Crazy” from ‘The Sound In Your Mind’ (1976)

I have to admit, tracking this one down took a minute. I would repeat this track often as a kid while listening to one of Willie Nelson’s box sets. After a while, I was able to find it on the 1976 album The Sound In Your Mind, and this entry on our list of Willie Nelson deep cuts appears to have been first released on that very album. It’s a personal favorite, of course, but it’s also a fine little deep cut that any Nelson fan would enjoy. It’s almost bluesy, but very much Nelson’s brand of country.