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The Best Willie Nelson Songs

By Deborah Crooks

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I was a child the first time I heard Willie Nelson’s voice — at once heartsick and sly, weathered and smooth, vulnerable and knowing — blaring from my best friend’s mom’s favorite country radio. This was Willie in full outlaw country glory, and while I was too young to fully appreciate what that actually meant, the fact that his music so powerfully swayed the adults in my orbit impressed me deeply.

Years later, when I saw him at Hardly Strictly Bluegrass in San Francisco, the puzzle pieces of his attraction coalesced. He turned in the direction of the crowd where I was standing, opened his arms and heart to the crowd and grinned a grin that seemed to light up the field, and that was before he started playing a signature set of his timeless songs.

So many of Nelson’s tunes can now be considered standards. Still going strong at 88 years of age — his last pre-pandemic show was performed to a crowd of 80,000 fans and his latest recording was released in November — it’s hard to pick 20 songs from his legendary cannon, but here’s a go:

20
Holler Country Music

Legacy Recordings | 2018

Last Man Standing

Long past the age he could have respectably hung up his pen and guitar and retired, it's beyond poignant to hear Nelson reflect on the reality of being an octogenarian who’s outlived quite a few of his peers with his characteristic acceptance of it all.

“I don't wanna be the last man standing / On second thought maybe I do / It's getting hard to watch my pals checkout / Cuts like a worn-out knife / One thing I learned about running the road / Is forever don't apply to life”, he sings.

19
Holler Country Music

Columbia | 1984

City of New Orleans

Steve Goodman’s ‘City of New Orleans’ is yet another great song that Willie Nelson rendered canonical when he included it on his 30th studio record.

As Nelson sings it, one feels every inch of the American highways and backroads he’s traversed, cities he’s visited and characters he’s encountered over his long career.

18
Holler Country Music

Columbia | 1978

Blue Skies

When a writer of classic songs offers up his own take of a quintessential pop song, he provides a master class in the form simply by revealing his choices, which Nelson does here by taking on 'Blue Skies'.

Included on a collection of standards, 1978’s Stardust, the choice was also a bit of a curveball, given that Nelson released the then-50-year-old song at the height of his outlaw country fame.

17
Holler Country Music

Legacy | 2012

Roll Me Up and Smoke Me When I Die

You can’t help but grin when you hear Nelson having the last word on both his lifelong habit and the way he plans to go out: high, happy and the life (or at least the reason for) the party.

The fact that his supporting cast on the record includes Snoop Dogg and Kris Kristofferson is simply icing on the cake.

16
Holler Country Music

Liberty | 1962

Three Days

Written by Nelson in the early 60s, I first heard 'Three Days' after he reinterpreted the song on his 1988 Teatro, featuring Emmylou Harris on backing vocals.

Another example of the endurance of Nelson’s lyrics, the later version found the song’s bitter regret now lived-in and metabolized.

15
Holler Country Music

Columbia | 1978

Georgia On My Mind

A great singer renders a flawless song transcendent, and Nelson did just that with this Hoagy Carmichael classic.

While it’s easy to get swept up in the pure romance and yearning of Nelson’s reading, he is also singing about the power of music here — “just an old sweet song / keeps Georgia on my mind” — as much as the lasting marks made by love.

14
Holler Country Music

Columbia | 1980

Angel Flying Too Close to the Ground

This haunted tearjerker of a ballad demonstrates Nelson’s economy of songwriting to a T while pulling on every heart string.

Depicting the healing power of love, given despite the consequences, it's a rare song about truly unconditional love: “Fly on, fly on past the speed of sound / I'd rather see you up than see you down.”

13
Holler Country Music

Atlantic | 1973

Whiskey River

‘Whiskey River’ was the first song I heard Nelson play live, when he opened his 2003 set with it at Hardly Strictly Bluegrass.

Even if drinking isn’t your thing, one listen to this song and you’ve entered Willie’s world of loving and losing hard, and finding a way through despite the scars.

12
Holler Country Music

Columbia | 1982

Always on My Mind

A cautionary tale for all of us muddling our way through life and love, the tear-stained regret and coulda-shoulda sentiment that permeate ‘Always on my Mind’ are universal, and seemingly tailor-made for Nelon’s interpretation.

While the song has been recorded numerous times by other artists (including Elvis), it was Nelson who took it to global renown.

11
Holler Country Music

Liberty | 1962

Funny How Time Slips Away

A bruised-heart masterpiece, first made famous by Billy Walker before Nelson claimed it for himself, ‘Funny How Time Slips Away’ finds our hero at his knowing, loved-and-lost, not-quite-letting-go best, its sentiment all the more meaningful as Nelson continues to sing it into his later years.

10
Holler Country Music

Columbia | 1993

Still is Still Moving to Me

If there’s anyone who’s figured out how to live a long and productive life, it’s Nelson, so one is served well by listening closely to what he chose to write and record in his later years. ‘Still is Still Moving to Me’ offers up some clues to the wells he draws from for spiritual sustenance.

“And it's hard to explain how I feel / It won't go in words but I know that it's real / I can be moving or I can be still / But still is still moving to me", he sings.

9
Holler Country Music

Columbia | 1980

On the Road Again

‘On the Road Again’ has always spoken to my own gypsy soul — and that of just about everyone else who loves the open road and the possibility of adventure it holds or dreams of escape.

An instant hit, the up-tempo track became another signature song for the optimistic, constantly-touring Nelson.

8
Holler Country Music

Columbia | 1993

Getting Over You

There’s a whole sub-genre within the vast Nelson catalog of duets with both male and female singers.

His collaboration with Bonnie Raitt on ‘Getting Over You’ from 1993’s Across the Borderline finds two of the most expressive voices navigating the mysterious undercurrents of the mature heart with equal finesse and emotional depth.

7
Holler Country Music

RCA Victor | 1965

My Own Peculiar Way

An early Nelson composition that he’s continued to reinterpret and rearrange throughout his career; a song that speaks to the mysteries of the abiding — and experienced — heart.

6
Holler Country Music

Liberty | 1962

Hello Walls

Another from his early hard-on-his-luck writing-for-other-artists period, ‘Hello Walls’ is genius for the pure daring Nelson had to be that honest about feeling so lost and heartbroken as to be talking to the walls and ceilings.

Everyone can and will relate to that feeling of near hopelessness at some point in their lives, which is why this song endures decades after it was written.

5
Holler Country Music

Columbia | 1975

Blue Eyes Crying in the Rain

Written by Fred Rose in the 1940s, ‘Blue Eyes Crying in the Rain’ is one of those classic country songs that seems to have always been in the air.

However, Nelson’s spare arrangement and been-there-done-that vocals on his 1975 recording brought both the song, and Nelson as an artist, into clear and undeniable focus.

4
Holler Country Music

Island | 2001

Rainbow Connection

Although it was penned by two other writers (Paul Williams and Kenneth Ascher) for a completely different voice (Kermit in The Muppet Movie), ‘Rainbow Connection’ functions as a sort of bridge from Nelson’s own, early-career song ‘Night Life’, especially when he sings “the lovers, the dreamers and me.”

3
Holler Country Music

RCA Victor | 1965

Night Life

As much a blues and jazz song, this genre-blurring gem has served as an anthem for many an entertainer since Wilson wrote it during his formative days as a songwriter for other artists. With deceptively simple and lean lyrics, it managed to convey both regret and self-respect.

2
Holler Country Music

RCA Victor | 1978

Mammas Don't Let Your Babies Grow Up to Be Cowboys

A Waylon and Willie classic, albeit written by Ed Bruce, Nelson’s rendition with Jennings epitomizes their outlaw country bromance, topped only by the version they did live with Johnny Cash and Kris Kristofferson as The Highwaymen.

Swaggering and unapologetic, it's a boast as much as it is a cautionary tale.

1
Holler Country Music

Liberty | 1962

Crazy

The gold standard of country songs - a gold standard love song period - Nelson wrote ‘Crazy’ early in his career amid a particularly fruitful week of writing.

Made famous by Patsy Cline in 1961, Nelson released his own version a year later and the song — which cuts to the quick of what it means to be besotted — has been reinterpreted countless times since.

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