I Know Why Willie Nelson Keeps Winning Grammy Awards

I Know Why Willie Nelson Keeps Winning Grammy Awards

Snow is white, time is short and Willie Nelson is going to be nominated for a Grammy Award next year.

These are three things we can depend on like the Dallas Cowboys being a disappointment.

In 2024, Nelson dropped two albums (The Border in May, and Last Leaf on a Tree last week), giving him 76 total. His output as he sets 100 in his sights is unheard of. Get this: The last year that came and went without Willie Nelson releasing a new album was 1992.

But please, allow him some grace. Nelson’s son Billy died by suicide on Dec. 25, 1991.

Most years, Nelson releases more full-length country albums than contemporary artists do radio singles. He’s prolific to the point that it’s embarrassing. Not to him — we’re embarrassed that we just can’t keep up with his catalog amid releases by artists who do more to steal headlines.

The Grammys are a curious awards show for country musicians. Kenny Chesney, Toby Keith and Eric Church help make a long list of stars who’ve never won — heck, Luke Bryan has never even been nominated!

There are three major country awards for solo artists at the Grammys: Best Country Solo Performance, Best Country Song and Best Country album. You can kind of predict the categories, or at least 60 percent of the nominees.

Chris Stapleton will get nominated in any year he’s eligible, as he’s should. He’s a premier vocalist and a great storyteller.

Luke Combs is in a similar spot, and everyone just kind of likes and cheers for him. It’s easy to vote for talent you like. The same is true for Carrie Underwood, although her pace has slowed in recent years.

After that, you’ll get one or two women who dropped a meaningful project, and an all-but-forgotten star. Tanya Tucker filled that slot in 2020. While I’m Livin’ album was a comeback record that marked a peak in her Hall of Fame career. She has not been nominated since.

Nelson is a constant thread who runs between the praised contemporaries and legend de jour. Six of his 12 Grammy wins have come after his 80th birthday, including two in 2023. They’ve come in the aforementioned country categories, but also in pop, American roots, bluegrass and roots gospel categories.

Older artists have won, but not many, and none with his kind of consistency.

Legacy Recordings

Legacy Recordings

To understand Nelson’s Grammy appeal, listen to his latest album. Last Leaf of a Tree (ineligible for next year’s Grammys) was produced by son Micah Nelson, who understood how his father’s minimalist approach to modern songwriting can pack a devastating punch. If they didn’t intentionally set out to package his response to losing just about all of his closest friends (most recently Kris Kristofferson), they stumbled into some very good luck.

Again and again, Nelson ponders his mortality with the kind of grace and pragmatism we all hope for.

“Do you realize / That everyone you know someday will die / And instead of saying all of your goodbyes / Let them know you realize that life goes fast,” he sings during a Flaming Lips cover of “Do You Realize?”

“Shadows are falling and I’m running out of breath / Keep me in your heart for a while / If I leave you it doesn’t mean I love you any less / Keep me in your heart for a while,” he sings, covering Warren Zevon’s “Keep Me in Your Heart.”

It helps (or hurts) to know this was one of Zevon’s final songs before he died from cancer.

“The wheels keep turning but they’re running out of steam / Keep me in your heart for a while.”

Micah Nelson said he bawled his eyes out listening to that one, and you may, too. It’s easy for the next generation to remain disconnected from any country icon so that when they pass, there’s barely a sting. Willie won’t allow it with his new music: Softly, he grabs your attention, and once you’ve spent a verse considering his life and death, you turn to yours, or your father’s … or your grandmother’s.

Beck, Keith Richards and Nina Simone are three more artists he covers. The title track is one of two Tom Waits songs. “I’m the last leaf on the tree / The autumn took the rest / But it won’t take me / I’m the last leaf on the tree.”

It’s satisfying to hear Nelson hasn’t yet entered the winter of his mortality, but each of those leaves has names we know too well: Cash, Jennings, Toby Keith, Guy Clark, Haggard, Pride, Kristofferson …

“I fight off the snow / I fight off the hail / Nothing makes me go / I’m like some vestigial tail,” he sings. A younger artist might snarl a lip singing those lines, but Nelson doesn’t need to flex like that any longer.

“I’ll be here through eternity / If you wanna know how long / If they cut down this tree / I’ll show up in a song,” he adds.

And the next year, that song will get nominated for a Grammy on its merit, and Nelson — by then working on album No. 80 — won’t show up to accept.

30 Pictures of a Young Willie Nelson

Willie Nelson began his music career in the late 1960s. Back then he wasn’t the typical country artist from Nashville — he was considered an outlaw.

Take a look back to his early years, and see photos of a young Willie Nelson that you may have ever seen before.

Gallery Credit: Evan Paul

PICTURES: See Inside Willie Nelson’s Historic $2.5 Million Rural Retreat

Willie Nelson‘s former home in Nashville is on the market for $2.5 million, and pictures show a splendid rural retreat that’s a true piece of country music history.

Nelson’s 3-bedroom, 1-bathroom hand-built log cabin, which the country music icon built for himself, sits on 150 rolling rural acres in Goodlettsville, Tenn., just half an hour outside of Nashville. The land surrounding the cabin offers a breathtaking slice of unspoiled Tennessee and ensures maximum quiet and privacy.

Gallery Credit: Sterling Whitaker

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