Willie Nelson’s Eleven Best Duets

In honor of the Texas hero's 80th Birthday celebration and legendary 4th of July Picnic, we're celebrating Willie Nelson Week here on DC9 at Night. Check back for interviews, retrospectives and more. When your career is as long, storied and diverse as Willie Nelson's, the group of musicians lining up...
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In honor of the Texas hero’s 80th Birthday celebration and legendary 4th of July Picnic, we’re celebrating Willie Nelson Week here on DC9 at Night. Check back for interviews, retrospectives and more.

When your career is as long, storied and diverse as Willie Nelson’s, the group of musicians lining up to share the stage will be equally impressive. Throughout his fifty-plus years making music, Willie’s proven an adaptable and generous singing partner. Here are 11 of our favorites, with video.

See also:
Willie Nelson’s Eight Best Movie Roles
Willie Nelson Turns 80: A Tribute and Playlist for a Texas Treasure
The IRS Tapes: How Willie Nelson Taught us To Care About Stuff That Matters, Not Money
How Willie Nelson Won the Lone Star State: Illustrated Map

11. Stephen Colbert
“You’re really high, I’m gonna tell your savior.” Stephen Colbert’s Christmas special aired on Comedy Central back in 2008, and featured an impressive guest list of singer-songwriters and George Wendt. Willie Nelson sang this number as the Fourth Wise Man, bearing a special herb as his only gift for the newborn baby Jesus. Willie’s charming sincerity makes for a perfect pairing with Colbert’s charming satire, who chimes in with backup lines such as, “Dude, man, dude.” –Aaron Ortega

10. Julio Iglesias
“To All the Girls I’ve Loved Before” was a huge hit for both members of the odd duo. It became Iglesias’ English language breakthrough and his biggest hit in the U.S. Willie received international acclaim for the song, and it has been covered repeatedly, including by Alanis Morissette in 2010. (LE)

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9. Kid Rock
One thing about Willie Nelson, he loves to share his music with other artists and often invites them to join him on stage. From Norah Jones to Toby Keith, Willie’s proven time and time again that his music is universal. But it’s his partnership with the “outlaws” of music that resonates in this Texan’s heart. Bob Dylan, two generations of Hank Williams and Keith Richards are pure metal. But it’s his collaboration with Kid Rock, who idolized the outlaws of country, that deserves recognition. “Last Stand in Open Country,” a song about outlaws, was their first duet together, but it’s their rendition of “Shotgun Willie” that stole the show.–Christian McPhate

8. Santana
Santana’s duets are hit (Lauryn Hill and Michelle Branch) and miss (Chad Kroeger and Sean Paul) but his rendition of “They All Went To Mexico” with Nelson, seemingly light-hearted and poppy but actually a meditation on death, was a hit. Seems to be a distant cousin to Dylan’s “Going to Acapulco.” –Lee Escobedo

https://www.youtube.com/watch?v=g4Sdn7YT9Bw&list=PLqCH6rwDueP-UyzHXs1eAAemKCXehBbHg

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7. Shirley Collie
The Hill Country hillbilly broke into the country music Top 10 in 1962 with a duet with his second-wife, Shirley Collie on “Touch Me.” Their marriage produced a string of collaborative hits, at times heart-breaking and tender and symbolic of their passionate, but short lived marriage. Note: Their version of “Touch Me” is not readily available for streaming online, so you’ll have to listen to “Willingly” and use your imagination. (LE)

6. Lee Ann Womack
In the wake of Carlos Santana cherry-picking pop-stars in order to revive his career, Willie released The Great Divide in 2002, a so-so album that featured some seemingly forced duets (Brian McKnight, and yes, Rob Thomas). Even though the album wasn’t near the blockbuster that Santana’s had been, Willie’s duet with country traditionalist Lee Ann Womack rivals some of Nelson’s greatest collabs. This is the one tune on the album where the oily-modern production didn’t kill the song, but gave it some life. The two Texas treasures proffered a song that was every bit as “smooth” as the pseudo-Latin fluff that Rob Thomas was shoving down our throats back then. (KD)

5. Neil Young
Written by Neil Young, in a style all so recognizably his own, “Are There Any More Real Cowboys” still embodies Willie’s legendary “outlaw country” songwriting from the days of Shotgun Willie or Red Headed Stranger. An ode to the disappearing romantic cowboy culture of living off the land and herding cattle, and not so much the flashy cowboy superstar country music eventually created, this duet tips their hat to the old rancher traditions. (AO)

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4. Merle Haggard
Also serving as the most well-known song for original writer, Townes Van Zandt, Nelson and Haggard turned “Pancho and Lefty” into a #1 hit on the country charts as the top single for their collaborative album, “Poncho & Lefty.” Also to note is the awkward and adorable album art for this album, featuring the two singers side-by-side, with Haggard resembling a middle-age Han Solo. (LE)

https://www.youtube.com/watch?v=fGWzobVD_Do

3. Waylon Jennings
When discussing Nelson duets, many will predictably – and perhaps understandably – begin with the Townes Van Zandt-penned classic “Pancho and Lefty.” But the fact of the matter is, without Waylon Jennings, there is no “Willie, Waylon and the boys.” Even though the famed Haggard-Nelson duet is about an outlaw, it didn’t capture the spirit of the so-called “Outlaw Movement” (a term that none of the alleged musical Outlaws ever gave a shit about) better than the 1972 classic “Good Hearted Woman” that Jennings and Nelson wrote together. With Jennings’ signature Telecaster work providing the rocking backdrop, the buddies kept things very honest about who they are and what it takes to love them. (KD)

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2. Ray Charles
Perhaps more than any other song from Willie’s gargantuan catalog, his performance of “Seven Spanish Angels,” with Ray Charles is the one — duet, or otherwise — that displays the supreme soulfulness that Willie can bring to a song. Paired with arguably the greatest soul-singer in history in Ray Charles, Willie rides shotgun as the pair bust out the greatest ever example of how country storytelling and gospel-soul music can be harmonious companions. Willie went on to make other seemingly odd combos work, including the 2008 album, Two Men with the Blues, a fine album he recorded with jazz-great Wynton Marsalis. (KD)

1. The Highwaymen
It’s not strictly speaking a duet, but such is the power of the gathering of some of country music’s most notorious outlaws in the Highwaymen that they defy the laws of online listicles. Formed in 1985, Johnny Cash, Waylon Jennings, Kris Kristofferson and Willie Nelson released their first album Highwayman to critical acclaim and soon followed with Highwayman 2 in 1990 and then again in ’95 for The Road Goes on Forever. But it’s the title track – “Highwayman” – off their first album that still resonates with fans, sending the haunting song to the top of the country charts. (CM)

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