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Songbook: A Guide To Willie Nelson's Voluminous Discography, From Outlaw Country To Jazzy Material & Beyond

Photos (L-R): Paul Natkin/WireImage, Gary Miller/Getty Images, Chris Walter/WireImage, Johnny Franklin/andmorebears/Getty Images

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Songbook: A Guide To Willie Nelson's Voluminous Discography, From Outlaw Country To Jazzy Material & Beyond

Prodigious songwriter, interpreter and national treasure Willie Nelson has released dozens or hundreds of albums, depending on who you ask. Still, a few key entryways and rabbit holes can help you get a handle on this foundational country figure.

GRAMMYs/May 4, 2022 - 01:59 pm

Presented by GRAMMY.com, Songbook is an editorial series and hub for music discovery that dives into a legendary artist's discography and art in whole — from songs to albums to music films and videos and beyond.

Cue up almost any Willie Nelson performance from the last 10 years, and you'll find something intriguing. Many other country greats are tight and precise onstage; Nelson is decidedly not.

While his Family band easily catches a groove on well-worn classics like "Family Bible," "Crazy" and "Funny How Time Slips Away," our permanently bandana-ed and pigtailed protagonist is attuned to deeper and stranger rhythmic dimensions. A Willie Nelson show is a particular kind of miasma — at times, it coheres; at times, it hovers almost beatlessly.

Sometimes, Nelson’s famously jazz-inflected syncopation threatens to swing him off the road — he'll strike his famously battered and weathered classical guitar, Trigger, at a moment that seems jarringly off the beat. His light and flinty voice has developed distinguished cracks and fissures with age. But if you're disappointed by his relative lack of polish, you're not just missing the point — you're missing the beauty.

First, nobody has ever picked up a guitar and sang a song like Nelson. The gods only made one of him, and the most fabulously expensive guitar on the market could never sound like Trigger. Second, the soul of country music is impactful storytelling and direct emotional transference, and nobody wields those twin abilities like Nelson, both as a songwriter and interpreter.

Indeed, without him as its cockeyed embodiment and one of its foundational figures, the world of country music would be unrecognizable — period.

Despite a few minor off-ramps during his almost seven-decade career, Nelson has built an astonishing body of work not via overhauling or reinvention, but becoming more himself every year. With every release, he digs deeper into his time-tested toolbox and aesthetic — often to heartening, comforting, and wizening results.

You don't approach the recently released A Beautiful Time, Nelson's fourth album in two years, for left turns; you do so because you want to know what the Beatles' "With a Little Help From My Friends" and Leonard Cohen's "Tower of Song" mean to him — as well as the state of his songwriting.

While the resin-caked hayseed vibe Nelson has embraced since the '70s may be a far cry from his crop-topped beginnings, you can drop the needle on any decade and hear an essentially unchanged artist and person. Whether he's channeling George Gershwin and crooning Broadway tunes, or running from the IRS on record — or even making reggae-inspired music, as on 1995's Countryman — Willie is Willie is Willie.

That said, the 10-time GRAMMY winner and 53-time nominee has either dozens or hundreds of albums, depending on how you count them. Where does one possibly begin? Given that he doesn't really have specific, delineated eras, it's more helpful to cherry pick the most essential albums, decade by decade, while still noting relatively minor entries of interest.

Let's go places we've never been, and see things we may never see again — in this edition of Songbook.

Listen to GRAMMY.com’s Songbook: An Essential Guide To Mastodon playlist on Spotify, Apple MusicAmazon Music and Pandora.

The 1960s

Willie Nelson backstage at "Arizona Hayride" TV show in November, 1964, in Phoenix, Arizona | Photo: Johnny Franklin/andmorebears/Getty Images

While Nelson made his first recordings in the mid-1950s, his discography began in earnest in 1962, with his debut album …And Then I Wrote.

…And Then I Wrote is absolutely worth hearing for its decadent production, introduction of Nelson's Django Reinhardt-inspired nylon-string picking, and key early compositions like "Funny How Time Slips Away" and "Crazy."

The baby-faced country crooner on the cover was in for the adventure of a lifetime. Listen to …And Then I Wrote, consider how Nelson's voice is pretty much the same 60 years on — albeit weathered by age and weed smoke — and you'll realize he essentially came out fully formed.

Do you dig the songs on …And Then I Wrote, but don’t like the semi-excessive reverb and instrumentation typical of Nashville back then? Head for 1965's Country Willie: His Own Songs for alternate versions of tracks like "Funny How Time Slips Away," "Mr. Record Man," and cuts from his second album, 1963's Here's Willie Nelson. But all in all, seek out 1973's The Best of Willie Nelson for a handy sampler platter from his first decade on record.

The 1970s

*Willie Nelson performs at the Great Southeast Music Hall on October 27, 1975 in Atlanta, Georgia | Photo: Tom Hill/Getty Images*

Forged and rebirthed by a ranch fire and divorce — not to mention professional bumps in the road — Nelson entered the 1970s with his first masterpiece: 1971's Yesterday's Wine, which contains classics like "Family Bible" and the title track.

Begin your trawling through Nelson's '70s with that record, then follow up with his 1973 breakthrough, Shotgun Willie, whose sound, attitude and songs helped forge the "outlaw country" subgenre. 1974's slightly less discussed Phases and Stages is a heady exploration of a marriage’s unraveling.

Then drop the needle on 1975's Red Headed Stranger, which further cemented Nelson's reputation as an outlaw-country mainstay and contained his immortal version of Fred Rose's "Blue Eyes Crying in the Rain." (Talk about making a shopworn song your own!)

If you want a more raucous Nelson offering from this decade, seek out 1976's The Troublemaker, a rough-and-tumble collection of traditional songs.

1977's To Lefty From Willie, a tribute to country singer Lefty Frizzell, is Nelson's first album-length tip of the hat to another artist — he'd later do the same for Ray Price and George Gershwin. And 1978's Waylon and Willie is worth engaging with simply to hear two titans appear on the same record.

The other 1970s entry you must hear is Stardust, which veers away from Nelson's outlaw-country image in favor of jazzy renditions of traditional pop songs, like "Unchained Melody," "All of Me," "Moonlight in Vermont," and — most famously — "Georgia on My Mind."

Given there has never been a jazzier country artist than Nelson, Stardust is a pivot point in his discography by concept alone — one that shows the true depths of his artistry. Seek it out for that reason, and stay for the luminous music.

The 1980s

*Willie Nelson performs in 1980 | Photo: Chris Walter/WireImage*

Nelson kicked off the '80s with San Antonio Rose, a collaborative album with Ray Price that illustrated the profound bond between two foundational country figures. Also released in 1980, Family Bible was a duet album with Nelson's sister, pianist Bobbie, who passed away in 2022.

A successor of sorts to 1979's covers album Sings Kristofferson, Music From Songwriter was a duet between the pair. It also soundtracked the titular, well-recieved 1984 film, which starred both men.

The one drop-dead essential Nelson album of the decade, though, is 1983's Pancho & Lefty, his inspired team-up with fellow outlaw-countryman Merle Haggard

The album featured unforgettable tunes like the Townes Van Zandt-penned title track — a narrative about a wanderer and Mexican "bandit boy" — as well as Haggard's "Reasons to Quit" and Jesse Ashlock's "Still Water Runs the Deepest." It also spawned multiple sequels, from 1987's Seashores of Old Mexico to 2015's Django & Jimmie.

The 1990s

*Willie Nelson in New Orleans, Louisiana, in 1994 | Photo: Paul Natkin/WireImage*

Nelson had a beyond rocky start to the decade: in 1990, the Internal Revenue Service seized most of his assets, claiming he owed a whopping $16 million. Long story short, he recorded Who'll Buy My Memories: The IRS Tapes to pay off part of the debt.

Although the album was well-received, it's safe to say it exists more of a reminder of this bizarre yarn than a standalone album worth cherishing. (Thank goodness Trigger survived the property seizure — Nelson's daughter, Lana, shipped it to him in Hawaii.)

A far more essential '90s Nelson listen is the haunting, stripped-down, Spanish-influenced Spirit, a quintessential "real heads only" album.

Featuring fiddler Johnny Gimble of Bob Wills and His Texas Playboys, Spirit consists solely of crepuscular, yearning originals, like "Your Memory Won't Die in My Grave," "Too Sick to Pray" and "I Guess I've Come to Live Here in Your Eyes."

Also of interest from this decade in Nelson's discography: Teatro, which Daniel Lanois recorded in an old movie theater in Oxnard, California and features vocal contributions from the estimable Emmylou Harris.

The 2000s

*Willie Nelson performs at The Mizner Park Ampitheatre in Boca Raton, Florida, in 2006 | Photo: Larry Marano/Getty Images*

In the young millennium, Nelson hit the road even harder than he did in the '90s, and collaborated with artists as divergent as Toby Keith ("Beer for My Horses"), Toots and the Maytals ("She is Still Moving to Me," "I'm a Worried Man") and Wynton Marsalis (2008's Two Men With the Blues).

The 2000s are also important in Nelson's development as they marked the start of his partnership with the two-time GRAMMY-winning producer Buddy Cannon. Their inaugural project was 2008's Moment of Forever, and Cannon produces or co-produces Nelson's yearly (or, in some cases, bi-yearly) albums to this day.

Other notable selections from this decade include 2006's Songbird, with Ryan Adams and the Cardinals, and 2007's western-swing excursion Last of the Breed, featuring the triple threat of Nelson, Haggard and Price.

The 2010s

*Willie Nelson performs on New Year's Eve at ACL Live in 2014 in Austin, Texas | Photo: Gary Miller/Getty Images*

Nelson was consistent and prolific throughout the 2010s. If you're a fan or just curious, you can conceivably drop into almost any album — from 2012's Heroes to 2014's Band of Brothers to 2018's Last Man Standing — and walk away smiling.

That said, a few stand out from the pack. Django and Jimmie, which marks Nelson and Haggard's sixth and final collaborative album, is by turns touching ("Somewhere Between") and uproarious (the irresistible stoner boogie "It's All Going to Pot").

What's more, Django and Jimmie is a glorious penultimate dispatch from the very missed Haggard, who died in 2016. Nelson touchingly paid tribute to his fallen friend on "He Won't Ever Be Gone," from 2017's excellent God's Problem Child.

Finish off your exploration of 2010s Nelson with 2018's My Way, a tribute to Frank Sinatra, and 2020's spare-yet-satisfying Ride Me Back Home.

The 2020s

*Willie Nelson performs at the Luck Reunion in 2022 in Luck, Texas | Photo: Jim Bennett/WireImage*

By all available evidence, Nelson is firing on all cylinders in the 2020s. He entered the new decade with 2020's tender First Rose of Spring. Nelson followed that up almost immediately with 2021's That's Life, another excellent tribute to Sinatra.

That year's The Willie Nelson Family reflected his eternal bond with his biological and musical family — Nelsons Amy, Bobbie, Lukas, Micah and Paula. And on April 29, Nelson gave us A Beautiful Time, a gorgeous collection of originals  and covers, with an especially touching title track written by Shawn Camp.

"If I ever get home/ I'll still love the road/ Still love the way that it winds," Nelson sings therein. "Now when the last song's been played/ I'll look back and say/ I sure had a beautiful time."

The song carries a tinge of finality, and on the cover, Nelson strolls into the sunset. Does it signal that Nelson is finally winding down? It'd be presumptuous to say so, even though he's numberless albums deep and will turn 90 in 2023.

Despite recent health issues, Nelson is magically, gratefully still on the road. He sings as well, or better, than ever. And his guitar playing alone remains an idiosyncratic force — to say nothing of his still-intact songwriting and interpreting talents.

For all his travails and triumphs, Nelson has remained creatively vital and deeply himself throughout his astonishing career and into his seventh active decade — partly because of his family’s support, partly for staying uncompromising, but also because he never let the old man in.

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A Tribute In Black To Johnny Cash

A star-studded roster of GRAMMY-winning talent celebrates the music and 80th birthday of Johnny Cash in Austin, Texas

GRAMMYs/Dec 3, 2014 - 05:06 am

Though Johnny Cash passed away in 2003, he's having a very good year in 2012. The latest in a series of events honoring the man in black — an 80th-birthday tribute titled We Walk The Line: A Celebration Of The Music Of Johnny Cash — drew a slew of GRAMMY-winning performers to Austin, Texas, for a lively Friday-night show on April 20 at Austin City Limits Live at the Moody Theater.

Top billing went to Cash's surviving Highwaymen brethren, GRAMMY winners Willie Nelson and Kris Kristofferson, who teamed with Shooter Jennings (son of late GRAMMY-winning Highwayman Waylon Jennings) and Jamey Johnson in a reunion of sorts on the song "Highwayman." Under a large banner bearing an image of Cash strumming a guitar, flanked by two silhouettes, Nelson also teamed with GRAMMY winner Sheryl Crow on "If I Were A Carpenter."

Crow sounded almost as if she were addressing Cash when she joked to Nelson, "I would definitely have your baby — if I could. If I didn't have two others of my own. And if you weren't married. And if I wasn't friends with your wife." 

Audience members cheered lustily in approval, as they did throughout most of the show, a taped-for-DVD benefit for the childhood muscular dystrophy foundation Charley's Fund. Just hours earlier, many of them had watched as Nelson helped unveil his new statue in front of the theater, which sits on a street also named after him.

The event was produced by Keith Wortman with GRAMMY-winning producer Don Was serving as musical director. Was recruited Buddy Miller, Greg Leisz, Kenny Aronoff, and new Rock and Roll Hall of Fame inductee Ian McLagan of the Faces as the house band. The handpicked all-star roster of performers ranged from Iron & Wine's Sam Beam, Brandi Carlile, the Carolina Chocolate Drops, Andy Grammer, Amy Lee of Evanescence, and Pat Monahan of Train to Ronnie Dunn, Shelby Lynne, Old 97's lead singer Rhett Miller, Lucinda Williams, and even Austin-based actor Matthew McConaughey, who, in addition to emceeing, sang "The Man Comes Around."

"We wanted a real broad, diverse group of artists," Wortman said backstage. "With Cash, you're as likely to find his music in a punk rock music fan, a heavy metal fan and a Nashville music fan, so he's not just a country music guy." 

GRAMMY winner Monahan, who sang Kristofferson's "Help Me Make It Through The Night," commented before the show, "I think of Johnny Cash as a style, as you would think of clothing, or music or whatever. He was his own thing. No can can really describe Johnny Cash entirely. 

"And no one could deliver a song quite like him," continued Monahan. "He sang hundreds of other songwriters' songs and he made those songwriters important because of the way he delivered what they were saying. There's not much that I don't respect about him, and I told his son [John Carter Cash] earlier that I'm almost more inspired by the love for his family than his music."

Lynne, who won the Best New Artist GRAMMY in 2000, sang "Why Me Lord," another song penned by Kristofferson, and delivered a spirited duet with Monahan on "It Ain't Me Babe," said Cash has influenced "all of us."

"We appreciate the majestic rebellion that Johnny gave us all in the music business. And he's also one of the great American icons of all time," she added.

Among the acts who earned the loudest applause in a night full of high-volume appreciation was the GRAMMY-winning Carolina Chocolate Drops, the bluegrass quartet re-exposing the genre's African-American roots. Their rendition of "Jackson" was among many highlights. Earlier, co-founder Dom Flemons revealed the personal inspiration of Cash's catalog.

"Johnny Cash's music has had an impact on me as a rock and roll singer, a country singer, as a folk music performer and great interpreter of song. I just love everything that he's done," said Flemons.

Bandmate Hubby Jenkins added, "Johnny Cash was really great about putting emotional investment into every song that he sang."

Co-founder Rhiannon Giddens said Cash’s core was his voice and his subject matter, and no matter how much production was added, it never diluted his message. 

Miller, who named his band after "Wreck Of The Old '97," a song popularized by Cash, said their intent was to sound like "Johnny Cash meets the Clash." He also recalled always picking "Ring Of Fire," a classic inducted into the GRAMMY Hall Of Fame in 1999, on the tabletop jukebox during childhood visits to a Dallas diner. 

"I didn't know what it was about, but I knew that the guy who was singing it was singing it with everything he had," said Miller, dressed in black in homage to "one of my all-time heroes." "And there was so much heart behind it, and so much conviction. And nobody could sell a song like Johnny Cash. He meant every word he said, and if he didn't mean it, he made it sound like he meant it."

(Austin-based journalist Lynne Margolis currently contributes to American Songwriter, NPR's Song of the Day and newspapers nationwide, as well as several regional magazines and NPR-affiliate KUT-FM's "Texas Music Matters." A contributing editor to The Ties That Bind: Bruce Springsteen from A To E To Z, she has also previously written for Rollingstone.com and Paste magazine.)

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Aloe Blacc, Melissa Etheridge, Wille Nelson Rock GRAMMY Foundation Legacy Concert

View Twitter and Instagram posts, video, photos and a complete set list from Lean On Me: A Celebration Of Music And Philanthropy

GRAMMYs/Feb 7, 2015 - 05:40 am

GRAMMY winners Melissa Etheridge, John Mellencamp and Willie Nelson were among the performers at Lean On Me: A Celebration Of Music And Philanthropy, the 17th Annual GRAMMY Foundation Legacy Concert. The sold-out event took place Feb. 5 at the Wilshire Ebell Theatre in Los Angeles and also featured performances by current GRAMMY nominee Aloe Blacc, singer/songwriter Rozzi Crane, violinist Lindsey Stirling, GRAMMY-nominated artist Robin Thicke, and indie pop/rock band Walk The Moon.

Below are highlights from the event shared via Twitter and Instagram, video recap, and a complete set list of songs performed.

Robin before the Legacy Concert tonight. #robinthicke #grammys #legacyconcert

A photo posted by Robin Thicke Fan (@gostupid4thicke) on

Aloe Blacc and Melissa Etheridge duet on "While My Guitar Gently Weeps" #LegacyConcert

A photo posted by GRAMMY Foundation (@grammyfdn) on

Set List:

Rozzi Crane
"Get Together"
"Ooh Child"

Aloe Blacc
"We Shall Overcome" (Pete Seeger cover)
"Love Is The Answer"

John Mellencamp
"Longest Days"

Willie Nelson
"On The Road Again"
"We Don't Run"

Melissa Etheridge And Aloe Blacc
"While My Guitar Gently Weeps" (Beatles cover)

Walk The Moon And Deborah Cox
"All These Things That I've Done"
"Heroes"
"Gimme Shelter" (Rolling Stones cover)

Lindsey Stirling
"Do They Know It's Christmas?" (Band Aid cover)
"We Are The World" (USA For Africa cover)

Plain White T's
"True Colors" (Cyndi Lauper cover)

Robin Thicke
"Fragile"
"Higher Ground" with Erica Campbell (Stevie Wonder cover)

Melissa Etheridge
"I Need To Wake Up"
"Lean On Me" (Bill Withers cover)

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Patriotic Makeover: State Song Edition

In honor of midterm elections, here are five state songs that might be due for makeovers

GRAMMYs/Dec 3, 2014 - 05:06 am

You can say what you want about Delaware's official state bird, the Blue Hen chicken. Or Utah's official state firearm, the Browning M1911 pistol. Or even New York state's recently appointed official state snack, yogurt. 

But only the most outspoken state advocates would likely defend songs such as "All Hail To Massachusetts," "Hail! Minnesota," "Hail! South Dakota," and "Hail, Vermont!"  

Let's face it, Massachusetts could find much more to brag about then: "All hail to grand old Bay State, the home of the bean and the cod." 

And then there's "Maryland, My Maryland," which contains lyrics that are downright scary: "She is not dead, nor deaf, nor dumb/Huzza! She spurns the Northern scum!" 

On the state level, there have been numerous legislative efforts to replace what some consider outdated anthems, but nearly all have failed. And federal intervention is, for the moment at least, off the table. 

But this is, after all, the electoral season, a time to keep hope alive. With that, here are five ideas for proposed official state song replacements.

State: Alabama
Official Song: "Alabama" (Julia S. Tutwiler/Edna Gockel-Gussen)
Proposed Replacement: "Shout Bamalama" (Otis Redding & The Pinetoppers)

It's tough to beat Tutwiler and Gockel-Gussen's 1931 lyrics, particularly the Jabberwocky-worthy "Broad the stream whose name thou bearest/Grand thy Bigbee rolls along/Fair thy Coosa-Tallapoosa/Bold thy warrior, dark and strong." But Otis Redding's first 45 rpm single (backed with his less-remembered "Fat Gal") is arguably more catchy and concise. And while Lynyrd Skynyrd's "Sweet Home Alabama" and the Doors' "Alabama Song (Whiskey Bar)" are both better known, neither can claim a chorus as fine as "I love a chicken, baby/Shoutin' Bamalama." 

State: Colorado
Official Songs: "Where The Columbines Grow" (A.J. Fynn) and "Rocky Mountain High" (John Denver)
Proposed Replacement: "Lucky Old Colorado" (Merle Haggard)

Yes, two state songs for the price of one. In 2007, before Colorado legalized marijuana, the state's legislature faced off on a measure to replace A.J. Flynn's ode to one plant with John Denver's alleged ode to another. The debate focused on a single line in "Rocky Mountain High" — "Friends around the campfire and everybody's high" — and whether it was a reference to elevation or drug use. One of the bill's co-sponsors suggested that it's really about "a bunch of guys who spent the day hunting or fishing and are having a couple six-packs." The easy way out was to adopt two separate-but-equal official songs, neither of which can compete with The Hag's beloved weeper about the state that stole the girl of his dreams.

State: New York
Official Song: "I Love New York (Steve Karmen)
Proposed Replacement: "New York State Of Mind" (Billy Joel)

While Frank Sinatra's "New York, New York" may be the gold standard, "New York State Of Mind" acknowledges the fact that there's more to the Empire State than five boroughs. Plus, Billy Joel was born in the Bronx, not Hoboken, N.J., where Ol' Blue Eyes got his start.

State: Ohio
Official Song: "Beautiful Ohio" (Ballard MacDonald/Mary Earl/Wilbert McBride)
Proposed Replacement: "Dayton, Ohio — 1903" (Randy Newman)

Ohio's official state song marvels at how "freedom is supreme in this majestic land" and "mighty factories seem to hum in tune, so grand," which was no doubt true when "Beautiful Ohio" was written in 1918. Subsequent songs about the Buckeye State, such as the Pretenders' "My City Was Gone," with its derisive refrain "Way to go, Ohio," have become a little less starry-eyed. Why not just go with Randy Newman's ode to pastoral nostalgia? "Sing a song of long ago/When things were green and movin' slow/And people stopped to say hello." All you'll need to do is get someone other than Newman to sing it, so that it will actually sound sincere. 

State: Wyoming
Official Song: "Wyoming" (C.E. Winter/G.E. Knapp)
Proposed Replacement: "Song Of Wyoming" (John Denver)

A consolation prize for Denver after he loses Colorado.

Can you name your state's official song?

(Bill Forman is a writer and music editor for the Colorado Springs Independent and the former publications director for The Recording Academy.)

Update: Willie Nelson Cancels Additional Tour Dates Due To Ongoing Illness

Willie Nelson

Photo: Rick Kern/Getty Images

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Update: Willie Nelson Cancels Additional Tour Dates Due To Ongoing Illness

The February cancellations come on the heels of three cancelled dates in January

GRAMMYs/Feb 7, 2018 - 12:47 am

GRAMMY-winning country legend Willie Nelson has now cancelled all tour appearances for the month of February, releasing a statement via his publicist that he is still dealing with the after-effects of a severe flu, and needs, "a few extra weeks to recover completely."

The February cancellations come on the heels of a scary incident in early January, which saw the singer abruptly cancel a San Diego performance partway through the opening song, leaving the stage with apparent breathing difficulties.  Following the San Diego show, Nelson was forced to cancel his three remaining January tour stops in order to recuperate. At the time, it was unclear whether the eight scheduled February shows would go on as planned.

Thankfully, it appears that the "On The Road Again" singer's condition is on the mend, as the press release makes clear that he is up and moving around and is, "healthy as ever," as Rolling Stone reports.

Nelson is now expected to return to the stage in Greenville, S.C., on Mar. 5. In a personal address, which was included in the cancelation press release, Nelson promises his fans, "I will see you all down the road."

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