Road songs, love songs, drinking songs, breakup songs, original songs, cover songs—Willie Nelson has a body of work to rival anybody. He seems to release three or four new albums every year (the latest installment is the T Bone Burnett production Country Music), and some (like 1998’s spectacular Teatro and 2009’s charming Asleep At The Wheel collaboration Willie And The Wheel) run the risk of getting lost in the shuffle.
Even his great songs are almost too numerous to corral. A few tunes that didn’t make this list (like “Opportunity To Cry” and “Whiskey River” and “Picture In A Frame” and “Reasons To Quit”) would be another man’s crown jewels.
At any rate, here are 10 timeless gems—the cream of the cream of the crop.
10. Blue Eyes Crying In The Rain
From the Red Headed Stranger album, which you may have heard of. It’s good.
9. On the Road Again
Some songs, like The Beatles’ “Yesterday,” for example, become so ingrained in the psyche that they’re almost not even songs anymore. They’re just part of the environment, like water and air. This one is in that same category.
8. Pancho and Lefty
Nelson is equal parts songwriter and interpreter, and he recorded this Townes Van Zandt song on the 1982 Merle Haggard collaboration album of the same name. The production sounds dated, but it’s still worth rescuing from the ‘80s graveyard.
7. Sad Songs and Waltzes
Willie slips into self-pity from time to time—okay, a lot of the time — and yet it’s hard to wind up not rooting for him anyway.
6. Last Thing I Needed First Thing This Morning
Endearing self-pity, part two.
5. Always On My Mind
This is the top-selling Willie Nelson song on the iTunes store, a wrenching mea culpa for a relationship gone sour. No joke: The Pet Shop Boys cover is wonderful, too.
4. I Never Cared for You
Love the atmospheric guitar intro. At first, you might wonder who’s playing those haunting notes. Then you watch the video, and it dawns on you. This is a song of bitterness and malice—or is it? Does “cared” mean that he never liked you, or that he never took care of you? The song hinges on this one word.
3. Heartaches of a Fool
Have you recovered from “Always On My Mind”? Then move on to this, an unheralded song with the same basic theme—it’s a man’s lament for ignoring his sweetheart, then facing the crushing reality of what he’s done. Look for the cover version by Phosphorescent, who recorded the song as part of the all-Nelson tribute album To Willie.
2. City of New Orleans
A slice of classic Americana, complete with a train ride.
Yeah, the Patsy Cline song. He wrote it. But you knew that, right?