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The Ultimate Willie Nelson Mount Rushmore—4 Songs That Define a Lifetime of Country Greatness. ML

How do you come up with the four best songs for someone with 100 albums and counting? The fact that Willie Nelson is still going at nearly 92 years old feels like a miracle in itself. Where do you even start? How do you parse out what’s truly essential or not? Can you even do that in a reasonable time period?

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Well, in an incredibly arduous effort, I did the due diligence. What I learned in narrowing it all down is that sometimes, the hits are hits for a reason. Don’t get me wrong, people can oftentimes be dumb and pick out some terrible songs on the vague notion of catchiness. But the biggest Willie Nelson songs are that big because they’re really that great. Trust me, my instincts were to pull one of his deep album cuts. I was awfully tempted to choose a song to represent his underrated oldies era where they chucked the Outlaw Country icon in a suit and tie. But truthfully, I had to settle for four of Willie’s hits and pick the best out of his illustrious career.

“Georgia on My Mind”

I always side eye people who don’t love Stardust as much as I do. Any arguments of the record not being properly country lacks an imagination of what the genre could truly be. Sure, it may not have that pedal steel or the fiddles but Willie Nelson alters the context by magnifying how tender and magical great country landscapes are.

It’s impossible to truly match how electric Ray Charles’ original rendition of “Georgia on My Mind” is because of how his soul soars on it. So Willie makes the tactful decision to go intimate; a sparse piano, a wispy guitar, and soft strings occupy the space before a harmonica howls into the night. He makes Georgia sound like the greatest place on earth, like he’s daydreaming in a dead end bar at 3am.

“Blue Eyes Crying in The Rain”

One of the most heartbreaking country songs to ever exist. Willie Nelson depicts Casablanca level tragedy here, where every word feels like his stomach is sinking. The remaining memories almost taunt him when his lover departs. It will never be enough to merely remember. It’s a tortured existence to live on knowing they’re gone forever and there’s nothing you could truly do afterwards. When he croons about the idea of ‘someday,’ we all know Willie is just coping so he’s not left with those ‘blue eyes crying in the rain’ again.

“Whiskey River”

No one on earth loves whiskey quite like a country singer. It’s an escapist haven for the greatest to touch Nashville. For Willie Nelson, it’s an excuse to bury bad memories where they belong. Depending on the day, it’s more of a best friend than his closest acquaintances ever will be. His hardened demeanor and deeper vocal register really sells it here. Nelson croons it like he’s already halfway through the bottle and plans on downing the whole thing by the end of the night. His eyes are sunken and he’s on the verge of slurring his speech. For anyone looking to empty their thoughts into a glass of booze, “Whiskey River” is the perfect record to throw on the stereo.

“Mammas Don’t Let Your Babies Grow Up to Be Cowboys”

There are three songs I find to be the quintessential country songs. You can debate two more to round out a top 5, you would spend all day trying. But these are the three for certain: George Strait’s “All My Exes Live in Texas,” Brooks & Dunn’s “Neon Moon,” and Waylon Jennings and Willie Nelson’s “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.”

Very few records quite capture the essence of country music at its truest essence. Strip away all the beers and women Brooks, Dunn, and Strait croon about on their records. You’re left with dirt underneath your boots, the thick humidity in the air, and the wide open road. Waylon and Willie do well to synthesize the cowboy experience into an existential quandary. It’s a lonely experience, where they might mysteriously wander off into the night, never to speak too much of how they’re feeling.

They make this brand of mystic masculinity sound awfully romantic and cinematic. But Waylon and Willie don’t wish this lifestyle on anyone because of how isolating it can feel. Still, their advice to make these young boys grow up to be ‘doctors and lawyers and such’ often falls on deaf ears. They make it sound too cool. Miranda Lambert puts it perfectly to Texas Monthly, “It’s so good. It makes me want to be a cowboy, real bad. In my next life.”

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