5 Times Chris Stapleton Covered The Heck Out Of Willie Nelson’s Most Classic Songs

Two of the genres most talented artists.

Chris Stapleton is an incredible vocalist, we all know that, so when it comes to the one person who can cover the legendary Willie Nelson and do him justice, he’s just about the only modern artist I know of who can really pull it off flawlessly time after time.

And thankfully, he does it pretty often, and they always wind up being some of my all-time favorite performances.

Willie is one of Stapleton’s musical heroes, and thankfully since Willie is still going and performing at 92 years old, Chris has gotten to perform for him a decent amount, notably at Willie’s Rock & Roll Hall of Fame induction ceremony in 2023. I can’t get enough of his flawless covers, and it got me thinking about some of the absolute best ones he’s done over the years.

Because I want all of you to enjoy it as much as I do, I’ve put together a list of five of the best renditions of Willie classics Chris has ever done, and I’ll be honest, it’s a GOOD list.

Do yourself a favor and check them out, you won’t regret it, and that’s a promise.

“Angel Flying Too Close To The Ground”

Stapleton performed this one at Austin City Limits earlier this year, and the show is one of the few musical variety shows left that brings in such a wide variety of high-quality artists every season, and allows them to display their unique and impressive talents to the world. This performance is next-level, as Stapleton belted “Angel Flying Too Close to the Ground,” which looked completely effortless and sounded perfectly simple and a little bit bluesy, in typical Stapleton fashion.

Of course, Willie originally wrote the song for his starring role as a country singer in the 1980 film Honeysuckle Rose, but the true inspiration behind it remains pretty vague and unclear. Some fans believe that because of the word “angel” in the title, Willie wrote it about his friend, Hells Angels biker Charlie Magoo, though Willie has never confirmed or denied that.

Willie has also hinted in the past that it’s actually about his ex-wife, Connie Koepke. And during live performances, he occasionally dedicates this song to his son Billy, the third child from his first marriage to Martha Matthews, who committed suicide in 1991.

This is pure country perfection:

“Last Thing I Needed, First Thing This Morning”

“Last Thing I Needed, First Thing This Morning” is one of my all-time favorite Willie songs. The classic country heartbreaker was written by Gary Nunn and Donna Farar, it was released as the third single from Willie’s iconic 1982 album, Always On My Mind, and eventually peaked at #2 on the Billboard Hot Country Singles chart. In my opinion, it’s one of the very best sad songs that has ever existed, and there’s just somethin’ about the way Willie sings the heartbreaking lyrics that cuts deep down in your soul.

And back in 2016, the great Chris Stapleton included a cover of it on his second studio album, From A Room: Volume 1. Chris’ version has since been certified Gold by the RIAA in July of last year, which means it has moved over 500,000 units since he released it in 2016. Quite an impressive feat, to say the least, especially considering that there were only two singles from From A Room: Volume 1 pushed out to country radio, which included “Either Way” and “Broken Halos.”

It’s stunning, and I go back to if very often:

“Always On My Mind”

If I absolutely HAD to choose one favorite Willie Nelson song, “Always On My Mind” would be it. It’s obviously one of the red headed stranger’s signature songs, and was written by Wayne Carson, Johnny Christopher and Mark James. It was actually originally recorded by Gwen McCrae as “You Were Always on My Mind” in 1972. It became the title track to Willie’s 1982 album, and a monster #1 single on the Billboard U.S. Hot Country Songs chart that year.

His version secured three wins at the 25th Grammy Awards in 1983, as Wayne, Johnny and Mark won Song of the Year and Best Country Song, and Willie won for Best Male Country Vocal Performance. More on that HERE. But Chris singing it at Willie’s 90th birthday celebration a couple years ago is something special, and I have been dying to get a studio version since this very moment.

It’s so special, and it’s absolutely flawless:

“Georgia On My Mind”

Not long ago, Chris joined Willie’s longtime harmonica player Mickey Raphael (who also joins Stapleton on the road) at the Brooklyn Bowl in Nashville, Tennessee for a great rendition of “Georgia On My Mind.” Of course, the classic song was written by Hoagy Carmichael and Stuart Gorrell and first recorded that same year by Carmichael. Ray Charles, a Georgia native, made it a massive hit and all-time classic when he recorded it for his 1960 The Genius Hits the Road album.

When Willie decided to record his iconic Stardust album in 1978, which was full of pop standards and produced by Booker T. Jones, his cover become a hit and shot to #1 on the country charts. In 1979, Willie won the Grammy Award for Best Male Country Vocal Performance because of the song.

The harmonica on so many of Willie’s songs, but this one in particular, is instantly recognizable for fans, and it’s all thanks to the great Mickey Raphael, who has been with Willie since 1973, when he was just twenty-one years old. I need more of this…

“Seven Spanish Angels”

In 2016, Chris teamed up with Dwight Yoakam for a performance of Willie Ray Charles’ “Seven Spanish Angels.” Written by Troy Seals and Eddie Setser, “Seven Spanish Angels” was recorded by Willie Nelson and Ray Charles in 1984, and released on Charles’ album Friendship, and then later included on Willie’s 1985 duets compilation album, Half Nelson.

It was the most successful of Ray’s eight hits on the country chart, as the single spent one week #1 one and a total of twelve weeks on the country chart. Alongside the angelic Morgane Stapleton, they KILLED it, and you have to check it out:

Come to think of it, after rewatching all of these videos to put this post together, I think we just need a Chris Stapleton covers album of Willie Nelson classic… he’s about halfway there anyways with these five songs, and I know it would be an incredible project that honestly, we need.

I never, ever say that about any sort of artist doing country covers of the genres legend, but of course, Stapleton is the exception, and even though it’s wishful thinking, I’m holding out hope for this to come to life one day.The post 5 Times Chris Stapleton Covered The Heck Out Of Willie Nelson’s Most Classic Songs first appeared on Whiskey Riff.