By Kelly Dearmore

In 2019, Country Music Hall of Famer George Strait released his latest album, Honky Tonk Time Machine. The record’s closing track, “Sing One with Willie,” provided quite the shock, even to longtime fans of perhaps the two greatest Lone Star State country music icons. Soon after the song’s twangy intro, Strait bemoans “I ain't never got to sing one with Willie.” 

Nelson joins in to sing along King George before the song’s over, but a cursory look at the lengthy list of Nelson duets makes it seem even crazier that these two giants hadn’t recorded a duet before. Nelson has never exactly been picky as to who he’ll lend a verse, having released numerous LPs full of duets. Perhaps there’s no better proof of Willie’s co-performing generosity than his 2005 duet with Jamaican great Toots Hibbert, “I’m A Worried Man,” or his 2008 joint effort with Snoop Dogg, “My Medicine.” 

Before we get too far in highlighting Willie’s best team-ups, let’s just assume we can all agree on unavoidable cuts like the Waylon Jennings collabs “Mama’s Don’t Let Your Babies Grow Up to Be Cowboys,” “Luckenbach, Texas,” and “Good Hearted Woman,” as well as the Merle Haggard duet “Pancho and Lefty.” These are all worthy of your attention, but need little highlighting at this point in time. For some essential Nelson duets beyond those instantly obvious picks, check out the list below.

“Faded Love” with Ray Price (1980)

While his cuts with Waylon Jennings and Merle Haggard rightfully rank as Willie’s most celebrated duets, this faithfully reverent take on the Bob Wills standard just might offer the truest essence of Nelson as an artist. As someone who has spent his career saluting the greats before him, hearing Nelson sing a classic from one of his heroes with Price, whose band Nelson played bass in during the early ‘60s, is the sound of country music perfection. 

“Gotta Get Drunk” with George Jones (1979)

Recorded in the midst of Jones’s downward career spiral due to drink and drugs, this duet succeeds in giving us an oddly humorous look into the mind of an alcoholic. The subject knows what he’s going to do and what will happen after he does it, but unsurprisingly, we never really learn why he does it. It all transpires over a killer arrangement that rollicks like a Friday night honky-tonk. 

“Reasons to Quit” with Merle Haggard (1983)

This classic collaboration from the Pancho and Lefty LP sounds just as good now as it did when it was recorded, unlike the record’s more famous, yet cheesy, title track. For all of the good time drinking songs this duo offered on their own over the years, this sorrowful song packs the kind of wallop their party tunes can’t.

“Seven Spanish Angels” with Ray Charles (1984)

Just like Willie, R&B titan Ray Charles could seamlessly shift between genres when the mood struck. They were overshadowed by his more traditional numbers, but Charles also claimed a number of country chart hits, including this glorious duet inspired by the Spanish-tinged ballads of Marty Robbins. Thanks to their respective takes on “Georgia on My Mind,” this pair will always be linked together in the minds of millions of music fans. 

“Mendocino County Line” with Leeann Womack (2002)

This Grammy-winning track from duets collection The Great Divide was Willie’s first Billboard country hit in many years. There were plenty of oddball collabs on this record - such as those with Rob Thomas, Kid Rock and Brian McKnight - that missed the mark, but this majestic number, featuring Leeann Womack in her post-“I Hope You Dance” prime, is a musical match made in heaven.

“My Bucket’s Got a Hole In It” with Wynton Marsalis (2008)

To truly love Willie is to be more of a jazz enthusiast than most country loyalists would care to admit. Willie has long held Django Reinhardt in as high regard as he has Lefty Frizell. The 2008 Two Men with the Blues joint record between Willie and jazz trumpet maestro Wynton Marsalis - recorded live at Jazz at Lincoln Center in New York City - featured plenty of jolly jewels, but none better than this reimagining of the Clarence Williams tune made famous by Hank Williams in 1949.


Kelly Dearmore is a music writer based in Dallas. He has written for The Dallas Morning News, Houston Press and Lone Star Music.


Photos: Flickr / Shutterstock