I will go to my grave maintaining two things: that “Pancho and Lefty” is the saddest song ever sung in this wide and lonely world, and that Toby Keith is a congenitally underrated musician and person.

1. The best, the definitive version, against which all other versions are ranked: Willie Nelson and Merle Haggard. 

(Some of the live Willie Nelson clips feature his controversial jazzy lyrical style; it sounds a bit rushed, as if he were trying to race ahead of the music. You either like this or you do not.)

2. Emmylou Harris 

3. Willie Nelson, Merle Haggard, and Toby Keith 

*Opens arms into Creed stance, falls into a sea of haters* Yes, the Toby Keith version goes above Townes van Zandt. He belongs there. Just because van Zandt wrote the song doesn’t mean he sang it best. Toby Keith is perhaps the greatest man in the world. He can turn the world on with his smile, and I love him, and I wish I could transform him into a shaggy red-coated dog that was my best friend and went on adventures with me and slept at the foot of my bed and wore a cowboy hat. This version’s a bit too glossy and uptempo, but it weirdly works, somehow.

4. Jason Isbell 

http://www.youtube.com/watch?v=WKnoKSDwY3A

That voice. This interpretation is a little more belt-y than strictly necessary, but that’s a minor quibble. Also notable for inspiring one of the most terrifying YouTube comments I have ever read:

“I always get a chill when I hear this song. Nothing sadder than an old killer, with nothing left but aches and pains…and memories. All the guys are dead, and gone, he’s left behind , still alive. Sometimes, in the dark , when no one’s around…he sits and drinks and holds his guns.”

5. Steve Earle 

You want someone to go Full Darkness, you want Steve Earle. This is the version that forces you to stare into the abyss.

6. Townes van Zandt

Only okay. But he wrote the song, and for that we must always be grateful.

7. Gillian Welch and David Rawlings 

Very slow, very subdued. For whatever reason this is the only version that does not make me actively sob, but it’s still quite lovely. Perhaps a little too lovely; this is not supposed to be quite so pretty.

8. Delbert McClinton 

Straightforward, workmanlike, efficient. Perfectly acceptable. “Pancho and Lefty” is equally good slowed down and sped up; this is because it is a perfect song.

9. Willie Nelson and Bob Dylan

I include this only so you can hear a version where Willie sings his verses slowly. Bob Dylan is garbage on this song. It makes me angry, to hear him sing this song. Bob Dylan, you are not taking the tragedy of Pancho and Lefty seriously, and you are a damned hippie. I — stop singing like that. Sing normal, with a normal mouth.

10. Darius Rucker and Kris Kristofferson 

This is a mess! A not unpleasant mess, but a mess nonetheless. Darius Rucker is a delightful man but he is wearing a suit. He is too polished by half for this song. Kris Kristofferson sounds like he is in so much pain that I want to bring him a shawl and a cup of tea. Also: what an odd song to sing at the White House! I love them both, however.

Worth mentioning: “Pancho and Lefty” has one of the greatest Wikipedia pages I have ever seen.

Two Interpretations of the NarrativeThe song is more a character study of the imperfect union between two bandits and how betrayal plays a part in the hero Pancho’s downfall, and how Lefty goes on in his life (“to Ohio”). Writing in “American Songwriter,” Jim Beviglia argues that Lefty did not betray Pancho, instead suggesting that the song contrasts the choice between going out in a “blaze of glory” versus growing old and gray — a theme also addressed by Neil Young. However, the line “Lefty split for Ohio / Where he got the bread to go there / Ain’t nobody knows” suggests that Lefty sold out Pancho, and in addition, a bandit character named Pancho, even if not directly in reference to the historical figure Pancho Villa, would have had a reward out for him. Further still, the federales likely wouldn’t have gotten Pancho without the betrayal of one of his friends (“We only let him slip away / Out of kindness, I suppose”).

/Sobs ineffably, fade to black.