Willie Nelson Says Writing Sad Songs Has Always Been A Challenge: “Something Meaningful And Deeper Is Harder To Write”

Willie Nelson country music
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Willie Nelson is the King of writing sad country songs.

And if you’re anything like me, then you know those are the best kinds of songs, especially when paired with some sort of alcoholic beverage and some good, moody lighting in case you’re in need of a good cry to go along with it.

With classics to his name like “Blue Eyes Crying in the Rain,” “Crazy,” “Last Thing I Needed, First Thing This Morning” and plenty more heart-wrenching songs that will quickly have you dropping a tear in your beer, so to speak (or even quite literally in a lot of cases), there simply isn’t a person better at writing sad songs, in any genre.

Back in 2002, the red headed stranger sat down for a wide-ranging interview with Playboy Magazine, where he revealed his secrets to writing what he describes as “the three-in-the-morning songs,” saying that they’re much harder to pen because it often means you’re digging much deeper to find meaning:

“Those are the three-in-the-morning songs. That’s when you may not feel so much like a joke. Also, as a songwriter I’m challenged by sad songs. They’re harder to write.

I don’t know, but I can knock off a happy ditty pretty easily. Something real—something meaningful and deeper—is harder.”

Willie continued, saying that the biggest challenge is taking those feelings and turning them into a bona fide country song (and if you’ve had too much to drink, that certainly makes it all the more difficult, but ironically can also help bring all of those feelings to the surface in the first place)…

Usually, you just hope you can remember it the next day:

“You may not be feeling all that happy when a song comes in the middle of the night. You may not be feeling so good because you had too much to drink or stayed out too late.

So the feeling might be there, but crafting it into a song is the challenge. And, of course, sometimes you’re fooling around on the guitar and suddenly you just played a piece of a new song and it wakes you up.

You think, What was that? I just wrote a song. Of course, then you can’t remember it [laughs]. All those lost songs.”

He added that while plenty of his saddest songs do come directly from personal experience, many of them have been inspired by his friends or people he’s met along the way who might’ve been going through a hard time.

Like any masterful songwriter, Willie knows that sometimes using stories from other people’s lives can be the best way to go about it and bring in a new perspective into his own catalog and repertoire:

“So the sad songs may come from sad experiences, but not necessarily. You draw on your past—the stories that you’ve heard, your friends’ lives.

If I write a song about breaking up with my girlfriend, it doesn’t mean I’m breaking up with my girlfriend. It means I thought it would make a good song.”

And actually, on this date in 1982, Willie was at #1 on the country album chart with his iconic Always on My Mind album, which became the Billboard #1 country album of the year.

In my opinion, the tittle track on that record is easily one of the saddest songs of all-time, and also one of my peresonal favorites.

While shockingly, he didn’t actually help write it (it was written by Wayne Carson, Johnny Christopher and Mark James), the delivery and longing in Willie’s voice is palpable, and the sincerity, believability, and most importantly, relatability, is otherworldly.

There’s also a great story about how it came to be that I think backs up Willie’s points about writing sad songs, which you’ll definitely want to heard about HERE.

Now seems like a good time to cue it up… gonna go have a good cry today:

“Always On My Mind”

A beer bottle on a dock



A beer bottle on a dock