25 Best Willie Nelson Duets

If you're a recording artist and you haven't laid down a track with the legendary Willie Nelson....what the fuck is wrong with you? Seriously, Willie has recorded or played alongside just about everyone that fucking matters. Listing all of Willie's duets and guest spots would be nearly impossible, he has like a bazzilion, so instead Muse-Zach brings you our 25 favorite Willie Nelson duets. (Note: List does not include any Highwaymen songs because the Highwaymen were essentially a group; which is good because they would have overwhelmingly dominated it.)


25) My Medicine w/Snoop Dogg & Luckenbach Texas w/Waylon Jennings
It was my last pick and I had a tie, mostly because I love both songs but they both contain only a little Willie on them.

Snoop explores the Nashville scene on this track, and though Willie is hard to place on this one; he's there. Snoop name checks him, he's in the music video, he plays some guitar on it, and he sings with Snoop on part of the chorus (though you'll have to listen closely to make it out). Snoop and Willie are friends have collaborated other places, Willie was added to a remix of one of Snoop's songs and Snoop joined Willie at a concert in Amsterdam last year to sing "Superman".


Another Waylon duet (there will be several more to come), I really like this song and he way Waylon sings it. Willie gets props from Waylon twice in the chorus, as he mentions Willie by name and also mentions one of Willie's most famous song (Blue Eyes Crying in the Rain). On the last run through the chorus, Willie finally surfaces taking over for Waylon. He swoops some of the lyrics, and finishes out the song strong.


24) They All Went to Mexico w/Santana

A laid back Mexican siesta kind of song. Santana, with guitar and backing vocals, helps Willie learn that everything has gone to Mexico.

23) A Showman's Life w/Gary Allan

In 2003, another young country gun cut a track with Willie. The song details the life of a showman, and how it isn't quite as glamorous as Superstars (like Willie) might let on.

22) Nowhere Road w/Waylon Jennings

Another great duet by the old outlaws. In 1996, marking the 20th anniversary of Wanted! The Outlaws, Willie and Waylon covered this Steve Earle with the same poise and grit that made the original album's duets so memorable.


Like A Soldier w/Johnny Cash

This track comes out of Unearthed a box set of unreleased tracks and alternate versions of songs Johnny Cash recorded between 1993 and 2003 for his America Recording albums with Rick Rubin. From the strenght of Johnny's voice I'm gonna guess this from the earlier end of that timeline, and though Willie only duets on the chorus, he certain adds an underlying power to Johnny's always exceptional voice.

20) Write One For Me w/Ringo Starr

Ringo Starr loves duets and guest spots almost as much as Willie. On this track, from Ringo's guest loaded 2003 album Ringorama, Willie and Ringo sing about getting other people to write them songs to match their feelings. Good stuff.

19) I'm a Worried Man w/Toots Hibbert

A cut off Willie's 2005 album Countryman, the old outlaw turns a classic song written by Johnny and June Carter Cash and turns it into a reggae hit with the help of Toots Hibbert. A sunny turn to a sad composition.

18). Maria (Shut Up and Kiss Me) w/Rob Thomas

A great song written by Matchbox 20's frontman Rob Thomas, who's vocals help Willie along here and there. A lot of people may find it disturbing or misplaced to have an elder state's like Willie singing about physical and seemingly modern love, but believe you me, Willie knows all about it.

18). Don't Give Up w/Sinead O'Connor

Off Willie's duet heavey 1993 album Across the Borderline, this duet is surprising but magical. O'Connor holds her vocals down to a mournful pledge "Don't give up" while Willie is the song's back bone, singing with grace and power.

17). Little Dealer Boy w/Stephen Colbert

From Stephen Colbert's 2008 A Colbert Christmas: The Greatest Gift of All!,
Willie plays the fourth wiseman bringing baby Jesus weed. Now the song is meant to be a joke, Willie obviously chosen because of his affilication with cannibus, but Willie sings it with such honesty and power that only Colbert's interjection "are you hight", keeps the song from completely escaping satire. Way to go Willie.

16). The Year That Clayton Delaney Died w/Waylon Jennings

A classic Tom T. Hall song mastered by the two outlaws. Off their 1982 album WWII.

15). One Too Many w/Aerosmith

The same song run through twice; once in country style and than in all out rock style. Willie schools Tyler in the Country department, and manages to stay with it when it turns rock and roll.

14). Slow Dancing w/U2

A slow beautifully haunting take on an old U2 b-side. The Irish lads had wonderful atmosphere and thin backing vocals.

13). Mendocino County Line w/Lee Ann Womack

A sweet young voice paired with an aged graveld one, "Mendocino Country Line" is about looking back on a passinate love that didnt last; somthing Willie certainly knows a lot about. Hitting the Country Charts at #22 in 2002, this bought Willie some exposure in the new milleniam and lead to some great duets with other female singers like Norah Jones and Shania Twain.

12). Last Stand in Open Country w/Kid Rock

A deep cut from Willie's excellant 2002 album The Great Divide, here Willie teams up with bad boy Kid Rock in a track penned by Elton John's lyricist Bernie Taupin. A Western odyssey about aging gunfighters and the young guns coming for their position, Willie certainly holds his, outsinging the Kid throughout. Why wasnt this released as a single?

11). Dead Flowers w/Keith Richards, Hank Williams III & Ryan Adams

Taped in a 2002 live concert honoring the living legend Willie Nelson certainly is, we get three generations of musicians running through a Rolling Stones Classic. All from different genres, all with widely different pasts, they shine together on this number.

10). I Hate Love w/Waylon Jennings & David Allen Coe

Legend has it that David Allen Coe asked to join the Highwaymen, but Waylon turned him down. On this track we get a little taste of what it might have been like if Coe would have been allowed in. Released in 1986 off Coe's Son of the South album, (one year after the first Highwaymen album came out) all three outlaws sing with great poise and power on this track, making it a not well know treasure.

9). Beer for my Horses w/Tobey Keith

Every new artist, if they got the balls, should write a duet with Willie Nelson. Tobey, established as a modern day outlaw, hit a home run with this duet in 2003 landing him and Willie a #1 on the Country Charts and #22 on the Billboard Hot 100. The songs about old school Texas justice, with a smart sing along chorus. Willie gets all the best lines in this one.

8). Heartland w/ Bob Dylan
In 1993, the two legends penned this song together for Willie's album Across the Borderline. Though I absolutely love Willie's opening performance, Bob steals the show on the second verse. His voice just sounds so downtradden and thirsty, perfectly emulating the lyrics. They should write more songs together.

7). Are There Any More Real Cowboys w/Neil Young

A great song written by Neil that runs through what it means to be a real cowboy, not just a superstar in a cowboy hat. Great lyrics, great voices, and the harmonica on this track ownes. Track was actually a minor hit on the Canadian Country Charts, topping out at #37 in 1985.

6). Rhythm of the Road w/Michael Martin Murphey
A deep cut from Murphey's 1976 album Swans Against the Sun, this is a fast paced banjo driven ditty about living on the road. Willie and Murphey continuously trade off verses back and forth in an infectious track that I could listen to over and over and over and over.

5). Man in the Big Hat w/Jerry Jeff Walker
One of the lesser known outlaws (unless you're from Texas), Jerry Jeff is best know for writing the amazing song "Mr. Bojangles", but he wrote dozens of numbers just as good. This is one of them. From is extrodinary 1988 album Live at Gruene Hall, Jerry tells the tale of an old Cowboy, just off the trail, relaxing in a bar while remembering his past and looking to the future. While Jerry narrates, Willie is the voice of the old cowboy and I love how rich and deep his voice is on this live track. I wish these two had done more songs together.

4). Mammas Don't Let Your Babies Grow Up to Be Cowboys w/Waylon Jennings

A warning to mothers everywhere and an insight into a cowboy's life, Willie and Waylon's second #1 duet together also won them a Grammy in 1978. Their voices, though distinct, just fucking rock and build off one another perfectly. I never grow tired of hearing these legends sing together.

3). Seven Spanish Angels w/Ray Charles

A western story about a woman and her husband being gunned by riders, this song is amazingly well written. A 1985 Country #1 hit single and the best of many duets Willie did with Ray, Seven Spanish Angels is amazing. Each singer nails their performance to a T, and than on the final run through the chorus, Ray Charles brillantly breaks from the song and jives like the true legend he was.

2). Pancho and Lefty w/ Merle Haggard

Written by a fellow outlaw, Texas' famous Townes van Zandt, this song details the life of an outlaw (possibly a mexican bandito) and the harshness and lonliness that comes with it. A #1 monster hit for both Willie and Merle (both the album and the song), though it was recorded by Townes and more famously by Emmylou Harris years before, Willie's weathered voice makes this track simply his and than when Merle finally comes in...oh man is fucking magic. Merle may had a larger role in this single if Willie hadn't woken him at 3 am to record it. Merle did his one verse in a single take and than when back to bed like a mother fucking bad ass.

1). Good Hearted Woman w/ Waylon Jennings
An honest send up to the hard working women behind every outlaw, it doesn't get any better than this famous track. Co-written by Willie and Waylon, (though Willie reportedly only added the line "throught tear drops and laughter we'll walk through this world hand in hand") it was a first recorded by Willie for his 1972 The Words Don't Fit the Picture album and than reached #3 on the Country Charts when released as a single by Waylon later that same year. Four years later, the live duet of Willie and Waylon would reach #1 on the Country Charts and #25 on the Billboard Hot 100 when RCA re-released the single from Wanted! The Outlaws, the first Country album to go platinum. Love this fucking song, especially when Waylon calls Willie into the duet after delivering the opening line.

*bonus*
We are the world w/The 80s

When Michael Jackson and Lionel Ritchie wanted to write a song to save Africa, they of course enlisted America's top 80's performers to deliver it. Willie was a no brainer, nailing his portion, and many people and artist have in the years since complained that the song sucked, I kind of liked it. It's fun to see all these different voices and genres of music coming together, and many of the artist give out standing performances (I'm looking at you Bruce Springsteen, Stevie Wonder, and Ray Charles). Funny, Willie's hanging in the back with Kenny Loggins.