Willie Nelson Duets
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11 of the Best Willie Nelson Duets and Collaborations

If you're looking for musical longevity, look no further than American outlaw country hero, Willie Nelson. In his eighties, the Grammy winner is still recording and touring like he was twenty years ago. And twenty years before that. Pick any Hall of Fame member, and they've probably written a song or two with the Red Headed Stranger (Merle Haggard anyone?). 

The Texas-born singer has worked with so many greats it was hard to narrow things down to fit into this list. From Carrie Underwood to Townes Van Zandt(he wrote the classic "Pancho and Lefty") and Loretta Lynn, the list could go on all day. After narrowing it down, here are our top ten favorite Willie Nelson duets.

11. "To All The Girls I've Loved Before" - with Julio Iglesias 

Nominated for Song of the Year at the ACM Awards and the CMA Awards, this duet is one of Nelson's best. It helped put Iglesias on the map on English radio and was a number one hit on the country charts. 

10. "Beer For My Horses" - with Toby Keith

This one makes the list just for sheer absurdity. Country music often deals in novelty hits, and this song about celebratory horse inebriation is no exception. "Beer For My Horses" tells the story of Texan vigilante justice. In the music video, justice in the name of dead prostitutes. For bonus points, check out Keith's B-side "Weed With Willie" to get a sense of what their sessions were like.

9. "Highwayman" - with The Highwaymen (Kris Kristofferson, Johnny Cash, and Waylon Jennings)

 The Highwaymen's biggest hit was this Jimmy Webb cover from their eponymous album, which they released in 1985. With its reverbed drums and synth sounds, it has a distinctly 80s feel to it. Some Highwaymen cuts feel overcrowded, which is the perfectly logical result of four gruff country boys singing at the same time. "Highwayman" has the members of the supergroup trade verses, each more desolate than the last. When they do harmonize, it's the best kind of chilling.

8. "Hard To Be An Outlaw" - with Billy Joe Shaver

The opener of Shaver's 2014 effort Long In The Tooth is all about aging, and it features plenty of the clever wordplay that makes country music so appealing. Both Shaver and Nelson are in their eighties, so naturally, their reminiscing will have a certain weight to it. The song finds the old hands lamenting not only the trials of their creaky stardom but the Nashville whippersnappers who "go and call it country / But that ain't the way it sounds." Thank goodness these desperados are still on the scene.

7. "Dead Flowers" - with Keith Richards, Hank Williams III, and Ryan Adams

Does it get better than these four gentlemen covering a Sticky Fingers classic? The live track appears on his 2002 live compilation Willie Nelson & Friends, Stars & Guitars, which features honorable mentions like Bon Jovi and Emmylou Harris. This cover is impeccable. The chorus gets pretty close to a religious experience.

6. "My Bucket's Got A Hole In It" - with Wynton Marsalis

Nelson and unofficial New Orleans spokesman Wynton Marsalis released Two Men With The Blues back in 2008, and the entire record is full of killer cuts. Their reworking of this folk classic is a standout. Hearing Nelson front over the bubbly dirge jam from Marsalis' band will put you in good spirits. Besides, we're sure Nelson is genuinely distraught at the idea of not being able to buy beer.

5. "Baby It's Cold Outside" - with Norah Jones

Sometimes the best duets are between two artists no one would ever think to pair. Nelson's rough rodeo vibe goes seamlessly blends with Jones's jazz fairy charm. This version of the Christmas standard is stripped down just right, giving Nelson and Jones room to balance each other out.

4. "Seven Spanish Angels" - with Ray Charles

Spend any time rifling through Nelson's discography, and you'll find plenty of southwestern and gospel influences, but rarely do you see them together. In this grand retelling of Romeo & Juliet, verse-chorus dynamics combine with impassioned performances to create something divine. Ray Charles always has the charisma of a preacher, so no surprises there. Nelson seems more moved than usual, and the results are otherworldly.

3. "You Remain" - with Sheryl Crow

The closing number on Nelson's 2002 record The Great Divide features Bonnie Raitt. This live performance from the same year has Nelson harmonizing with Sheryl Crow on a somber look back at an old love. Nelson tends to prefer balladry when he sings with women, but this track is special. What begins as a sort of understated "The Way It Is" swells into rolling hills of gorgeous, bittersweet regret. Both versions are magnificent, but Crow has a slightly bigger vocal role in hers, making it that much more breathtaking.

2. "Mammas Don't Let Your Babies Grow Up To Be Cowboys" - with Waylon Jennings

This is arguably one of the best hits produced by the outlaw country movement. The dusty duet originally appeared on 1978's record, Waylon & Willie. The mournful maternal plea has been recorded by many, but this version has by far been the most popular. Though the pair's ranching experience is minimal at best, they sure knew what it meant to be lonely on the road.

1. "Roll Me Up And Smoke Me When I Die" - with Kris Kristofferson, Snoop Lion, and Jamey Johnson

Released on green vinyl for Record Store Day 2013, this hilarious ode to the world's favorite drug has Nelson and friends making a pretty peculiar will & testament request. The bouncy, juke-y tune features fellow Mary Jane enthusiasts Snoop, Kristofferson, and Johnson, crooning over plenty of honky tonk and a smattering of accordion. Say what you will about Nelson's indulgences, but everyone who goes to his funeral is bound to have a really good time.

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