meta-scriptSongbook: A Guide To Willie Nelson's Voluminous Discography, From Outlaw Country To Jazzy Material & Beyond |
Photos of Willie Nelson throughout the decades for Songbook series on
Willie Nelson throughout the decades

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


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, 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’s Songbook: An Essential Guide To Willie Nelson 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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Billy Strings
Billy Strings

Photo: Christopher Morley


Billy Strings On His Three GRAMMY Nominations, Working With Dierks Bentley & Willie Nelson

When Willie Nelson asked Billy Strings for instructions in the studio, he thought, 'I'm nobody, dude; you're Willie Nelson. You're asking me?' But Strings is certainly somebody: he's up for three golden gramophones at the 2024 GRAMMYs.

GRAMMYs/Jan 18, 2024 - 04:44 pm

Is it possible to write someone else's song for them? Which isn't the same as being an outside writer: it's writing something that spiritually belongs to your influence. That's the sensation that came over guitar and banjo picker Billy Strings, when he wrote "California Sober."

"California Sober" had the lilt and thematic ring of something like Willie Nelson and Merle Haggard's 1983 hit "Reasons to Quit"; in fact, it felt like it emanated from Nelson entirely. Which makes sense, given that Strings had just hit the road with the country patriarch.

"I don't think I would've recorded the song if Willie wouldn't have wanted to do it with me," Strings tells "It's like, I'm not even going to cut this unless Willie wants to do it. It would just be like ripping off Willie's sound."

Exhilaratingly, the Red-Headed Stranger accepted — and their resultant duet of "California Sober" is nominated for Best American Roots Song at the 2024 GRAMMYs. And that's just the beginning of his prospects at Music's Biggest Night, coming up on Feb. 4.

At the 2024 GRAMMYs, Strings also picked up a nomination for Best Bluegrass Album for Me/And/Dad — his album with his bluegrass old-timer father, Terry Barber. And Dierks Bentley's "High Note," featuring Strings, is up for Best Country Duo/Group Performance.

Read on for an interview with Strings about how these albums and songs came to be, and what he learns from Nelson, Bentley, and Béla Fleck, and much more.

This interview has been edited for clarity.

Tell me about your relationship with the Recording Academy, and the GRAMMYs.

Well, the last few years, let's see: we were nominated for Best Bluegrass Album for Home, and we won that [in 2021]. And the next year we were nominated for two different things. Can't really remember, but we didn't win anything. [Editor's note: Strings received nominations for Best Bluegrass Album (Renewal) and Best American Roots Performance ("Love And Regret").]

That was when I went out there and checked it out, and had a great time being on the red carpet and seeing all the crazy outfits and stuff. And it's kind of crazy because although we didn't win, my friend Béla Fleck won.

I played on [his] record [2021's My Bluegrass Heart]. I was so honored to play with Béla Fleck and all those amazing musicians on that record, and it's been like 20 years since Bela made a bluegrass record — it's like, man, he deserves it.

And that was a big moment in my life — being in the studio with those guys, making that record. I still look back and I'm grateful to Béla for giving me the opportunity to do that because it gave me so much more confidence in myself. I still get almost emotional when I think about Béla actually asking me to be on his record because it just means so much to me. It's just always been kind of crazy. I'm just completely flabbergasted and honored because I never thought I'd be nominated for a GRAMMY or anything — let alone we won one already.

[Me/And/Dad] is probably the most important record I'll ever make because it's with my dad. And I think it's an important record for bluegrass too, just because of the songs and kind of the way we played those songs. And there's an old style that, as time goes on, the guys who sing and play like that are kind of dying off.

My dad's one of that older guard, and he just has this beautiful voice and amazing guitar playing, and he taught me everything I know about bluegrass music and it's deep in my heart and soul. It was so cool to be able to call my dad and say, hey man, guess what? Our record got nominated for a GRAMMY," and he's like, "Holy s—."

Can you drill deeper into why it's the most important thing you'll ever make?

Because everything I know about music, and bluegrass, I learned from my dad.

He started me off really young in my childhood; it was so based around the music. All the sweet memories that I have from when I was a boy were based around bluegrass music, and it seeps into your heart and soul and gets under your skin in a way that I guess only bluegrassers could really know.

It's music that can make me cry and make me laugh, and it gives me déjà vu, and it's almost a portal directly to my childhood back before I knew anything dirty about the earth. It was back, simpler times, just hanging around the campfire, picking music, and with my family and just beautiful times. 

And whenever I get together with my dad and play, it brings me back to just being a little boy.

And can you speak more to the importance of Béla Fleck? I interviewed him at Newport Folk, and he couldn't have been kinder nor gentler, with a fraction of the ego he could rightfully have.

He's the best man. He's become a good friend of mine. Obviously, he was my hero first. And so that's always good when you meet your heroes and they're really cool people. It means a lot.

And he's just like any of us; he's constantly just playing and trying to write and get better. He said to me one time, "We're all just trying to keep our heads above water," 'cause maybe I was feeling down about my playing or whatever, he's like, man, we're all doing the same thing.

What he's done for new acoustic music is incredible. The things that he's done with the five string banjo, and not only him, but his bands like the Flecktones and New Grass Revival with Sam Bush and John Cowan and those guys just, that's a big inspiration to us up and comers that are playing bluegrass music but like a little bit more progressive side.

I listen to everything from heavy metal to hip-hop and jazz and everything, so it's kind of sweet when you can take bluegrass instruments and play any kind of fusion music. And Béla is a huge innovator in that world.

One thing he told me was, "There is no best." I'm sure that resonates with you in some way.

Yeah, absolutely. Everybody's kind of the best at what they do. I'll never be as good as Tony Rice, ever — not if I practice eight hours a day for the rest of my life. I'll never touch him. But if I just kind of focus on what I'm doing and try to invent my own voice, maybe I'll be the best one at that.

How would you characterize that voice you've developed?

Well, I was raised playing bluegrass music — pretty traditional bluegrass. And then in my teenage years, I veered off and played heavy metal and got into more writing songs and just lots of different music other than bluegrass.

But when I came back to bluegrass, some of those things kind of stuck, particularly the stage performance thing. A lot of bluegrass bands, I feel like just stand there and play, 'cause they don't really have to do anything else. I can't help but move around and jump around and bang my head and stuff like I used to in a heavy metal band, 'cause that's how I learned to perform.

I've seen people be like, man, this is not headbanging music. And I'm like, "Well, hell yeah, it is."

Can you talk about Dierks Bentley, and "High Note," and the road to the nomination for Best Country Duo/Group Performance?

Dierks is a good buddy. He's just a real dude. I met him a few years ago. I was walking down the street, I was going to lunch with [flatpicker] Bryan Sutton and this white pickup truck pulled up, and Brian's like, "Oh, hey, what's up, man?"

We started talking. I didn't even know who it was. And the inside of his pickup truck was a mess. It was just like, s— everywhere, tapes and old, just like my car. So I'm like, okay, well, who's this guy? And then I realized he's a big country star, and I liked that he was a big country star and drove around with a messy truck.

Are you a messy truck guy too?

I try to keep it pretty nice nowadays, but yeah, usually my s— gets trashed. There's like fishing lures and just bulls— everywhere.

So I don't know, that made an impression on me for some reason — the inside of the cab of his truck. But after that, we became buddies and we had picked a couple times. He's a good buddy of [mandolinist] Sam Bush as well and so that's kind of a mutual friend of ours.

And there had been a couple times on stage where me and Sam were playing with Dierks, and he can play some bluegrass, man. He knows a lot of bluegrass songs and stuff.

So when he hit me up to do this song with him, I was like, of course, but especially when I heard it on a high note, he knows I like to smoke a lot of weed and stuff, so it was kind of like the perfect song for me. And it had that bluegrass flavor so I could jump on guitar and sing the tenors and stuff, sing the harmonies and stuff.

How popular is weed in the bluegrass community?

Well, I mean, in our scene it's pretty popular, but there's also folks that don't like to see me up there smoking or anything… maybe the more old-school kind of conservative types. But I just do my thing, man. I'm not trying to hurt nobody.

Speaking of, we have "California Sober" with Willie Nelson.

Man, so, Willie Nelson, holy f—.

Yeah, dude.

Wow, I love him so much. My grandpa loved him a lot, and my mom. When I grew up, my dad would, he'd be singing "Blue Eyes Crying In The Rain" and all them songs, and a lot of songs off Red Headed Stranger, I heard growing up — my dad singing those, and my grandpa playing the records, and stuff.

Willie was a big deal, especially to my grandpa, and he's been dead since 2001. So I always think about my grandpa when I think of Willie too, 'cause he loved him so much. If my grandpa was around to hear this song, he would just lose it.

And the way that it came about was, I went on tour with Willie on his road show, The Outlaw Tour, and we were one of the bands on there. And during that tour, Willie invited me up on his bus, and we hung out for a little while and just shot the s— and told jokes, and he told me how he got Trigger and everything, and talked about Django Reinhardt and Doc Watson.

I just had a great time. It was like hanging out with my grandpa or something, and I had a great time on the tour. And when I got home from that tour, I was sitting out by my burn pile and I ripped off this piece of cardboard, and I just had this tune going in my head, "I'm California sober, as they say / Lately, I can't find no other way."

I just wrote it down on this piece of cardboard. And then I went inside and kind of started writing a song — and I realized that I was writing a Willie Nelson song. I was so inspired by being on the road with Willie that I came home and I wrote this song — it's like I wrote it, but it was such a Willie song.

So what happened next?

I had my manager reach out to his manager, or whatever, and say, "Hey, here's this song that I wrote. Would you want to do it with me? And the answer was a resounding, 'Hell yes.'"

We made the track here in Nashville with me and the band, and then I went down to Luck, to his studio down there at his home in Texas, and Willie came in and we just hung out for a while, man. He sat down in front of the mic and he said, "Well, what do you want me to do?" And I was like, What the hell? I'm nobody, dude; you're Willie Nelson. You're asking me?

But he was like, "Well, do you want me to sing a verse?" I was like, "Tell, try to sing harmonies on the chorus and then take a crack at that second verse." So he put the harmonies on the chorus just fine. And when he got to this verse, it seemed like he was kind of just still learning the words a little bit, and I don't know if something [happened] like, he got frustrated on one take or something.

The next time, he just nailed it, and it was like this young Willie voice came out and he just sang so beautifully, and I had goosebumps, and it was just incredible, man.

And then right after that, he finished his part, he said, "We got it?" And I said, "Man, I think we got it. He said, "OK, let's go play cards."

So we went out back to his little spot there, where he's been playing cards for 50 years with everyone, Johnny Cash and Kris Kristofferson. His old buddy, Steve, [was there]; we were sitting there playing poker, and… I'm sitting there playing cards with two old buddies who have been playing cards together for 50 years, man. Hearing those two talk s— to each other, man.

They took a thousand dollars of my money real quick, and I would've paid another thousand just to sit there at that table and hear them bulls— each other.

What will your call with Willie be like if "California Sober" wins?

I'm going to say, "Hey, man, I'm coming to get my thousand dollars back."

Béla Fleck Has Always Been Told He's The Best. But To Him, There Is No Best.

Jessi Colter
Jessi Colter

Photo: Chris Phelps


Jessi Colter's New Album 'Edge Of Forever' Is Timeless In Every Sense Of The Word

On 'Edge of Forever,' the 80-year-old outlaw country star doesn't sound like an elder stateswoman. Her latest could have been released in 1973 or 2013.

GRAMMYs/Oct 31, 2023 - 02:20 pm

As one of the lone women in the outlaw country milieu, Jessi Colter has navigated the music industry with grace for more than half a century — through false starts, lulls, and the death of her husband and collaborator, Waylon Jennings.

But while some living legends can feel a touch frozen in time, Colter is constantly in motion.

"We've just returned home a few days before the Hall of Fame performance, and my house is a wreck," she reports to, upon landing back in her Arizona climes. During a brief  conversation, she's speed-eating lunch and jumping in a car; she even suspects this interviewer was multitasking as well. ("Are you doing dishes?" Colter inquires, in response to an errant clank over the line.)

That consistent movement — of body, of creative practice — allowed Colter to cook up one of her most inspired albums. Edge of Forever — produced by GRAMMY nominee Margo Price, and mixed by Colter's son, three-time GRAMMY winner and five-time nominee Shooter Jennings.

Backed by Price's crack band, tunes like "Standing on the Edge of Forever," "Lost Love Song" and "Can't Nobody Do Me Like Jesus" crackle with potency — and have all of the impact of her early work, prior to all these spins around the sun.

But this timelessness doesn't mean it's simply retro, or '70s; it moves through time. Edge of Forever couldn't have happened without the lumps she's taken in the country machine, or the jubilations.

Furthermore, it proves that the hitmaker behind "I'm Not Lisa" and "What's Happened to Blue Eyes" back in '75 remains a force — as a feisty, vital country-music matriarch. Below, Colter chats with about Edge of Forever, and what's on the other side.

This interview has been edited for clarity.

Congrats on the release of Edge of Forever. I think the word "timeless" gets thrown around a little too much, but the description fits here.

I had one fellow, I asked him how old he was. I figured he was 20 or 28 and he was 60. I think it was [for] Variety. When I first talked to him. And he said it just has such a feeling that it takes him back to the '70s, and I wasn't sure what he meant exactly. I just am who I am and that's who I'll always be.

But anyway, he loved it. He said it really felt, for him, comfortable. And I understand what he's saying. There's a whole lot out there that's not so comfortable.

Interesting. What do you hope people take away from your music?

Well, certainly that, and I hope I communicate with feelings they've had. I loved it on "I'm Not Lisa," when the little girls would send me tapes of themselves singing it. I thought I have communicated, because when I write it's very inward of my experience or somebody really close to me and so forth. So that's how it goes.

Take us back to your early conception of Edge of Forever — the spark that lit a flame.

Well, I had songs. And I became acquainted with Margo, and she helped me out on a Facebook flash [giveaway] of my book An Outlaw and a Lady, for Harper Collins, that I wrote with David Ritz.

And this was 2015. She was pregnant with Ramona when we cut this album and she was about to have the baby. So as far as the genesis, it took two or three visits together, and [her husband] Jeremy [Ivey] and she both intimated that they would love to see me do an album.

It was years later that we did it. And we did it quickly and directly, because she was about to have her baby. And so it didn't take the kind of time that I'd taken on other albums, but it's taken time to wind its path to the yellow brick road, which seems to be Appalachia Records, who she'd worked with before.

[Label owner Loney Hutchins is] great to work with, and I've never worked with a small label that worked with other indies. But anyway, they've been terrific. And so we just kind of were drawn to each other. And I had these songs that she reacted to, and then there was a couple others, then one written on the spot.

And so it just happened and now it's taken the legal teams, and the manager — this and that, so forth. Anyway, it's worked out. It worked its way to here.

Can you talk about your dynamic with Margo and Shooter?

Yeah, it's fantastic. It's easy. I've worked with Shooter before on The Passion of the Christ, where he wrote on the spot with me. It was an album that went with The Passion of the Christ; It wasn't a soundtrack.

We wrote a song called "Please Carry Me Home." If you haven't heard it, try it, because we wrote it and he produced it on the spot. Then [my daughter] Jennifer [or Jenni Eddy] and I actually wrote "Secret Place," which is on this album, a number of years ago.

Waylon was still with us, and he heard that song — and he didn't often say just this, but he said, "You've got to do that." And it's just been in my pocket.

Often, artists keep songs that inspire them. They don't use them until the time is right. And so there were a number of songs that I had been holding onto. "Lost Love Song," "Can't Nobody Do Me Like Jesus." I totally rewrote that spiritual except the bridge.

Anyway, the dynamic was fantastic with Margo, with Shooter, with Jennifer Eddy Jennings, my daughter; her father is Duane Eddy. Waylon was a wonderful father to her. So, it's been a gift; the whole thing has been a gift for me.

Working with Jenni Eddy must have a gift among gifts.

Oh, yes. She's so gifted and a great singer. She just hasn't come into the public yet, but she's working on a number of things.

And Struggle Jennings, my grandson, recorded a great album with her called Spiritual Warfare, where Struggle is rapping. [Jenni] sings, and she wrote the songs, and then he raps. And it's interesting.

I don't know what she'll end up doing. Her voice is much more melodic than mine, and she sings beautifully with me. It would be worth working to her and Jenny Lynn Young accompany me, if and when I perform. It''s magnetic, the whole thing.

As a singer/songwriter myself, even something I wrote a year ago can feel alien to me today. Can you talk about reacquainting yourself with tunes from many years ago?

I understand that, but if you love a song to start with, you'll always love it. And so that's how it went with me.

"Maybe You Should Have Been Listening" was one of Waylon's favorites on my classic albums, and "With or Without You" was something I wrote a number of years back for a girlfriend of mine who went through being stood up by a well-known man right before their wedding.

Little Stevie Van Zandt loved that song: "With or without you/ I'll go on alone… And like Bob Dylan said, if it's not right, it must be wrong." I love that. And if people would remember that. "Angel in the Fire" I wrote some time ago. I love it every time I sing it, with Lisa Kristofferson in mind.

"Lost Love Song" was a song that I held in my pocket to inspire me. It is talking about the prison of love. I never have been able to find who wrote it. He may be living, he may not, because I had this years before Waylon went, which was 2002.

"Hard On Easy Street" was great fun. I did it on an album that I [do not] yet have the right to publish. Never came out. It's a great song. "I Wanna Be With You" is always an upper, and percussionists particularly love that song because it's such a rhythm.

"Standing on the Edge of Forever" was a new song I wrote in the last 10 years [about]a relationship that just won't come together, and that's what that's about. But it's also, as Lenny Kaye edged me on to say, This is it, either or. It's that time you come to and it's enough of whatever it is, get on or get off.

"Can't Nobody Do Me Like Jesus" — oh, that's one of the great songs of all time. James Cleveland wrote it, but I rewrote it. But I don't find to ever get any income from that.It's just a great song talking about how it is. If you're going to do right, you may be alone.

"Fine Wine", Jennifer wrote that with some accompaniment by Margo, and it's talking about early widowhood. And it was how it was maybe four years ago, even though that was a 16-year mark of loss for me, I had been alone for 16 years when I said I'm open for love.

And as things work out and good things happen, I met my current husband, a rancher, horseman from Wyoming, and took it a few years to kind of get to know each other, but we're having a good time.

With Edge of Forever out in the world, what are you looking forward to in the near future?

Right now, I'm looking forward to a documentary I've been working with [a production team] on for eight years. It's called They Called Us Outlaws. Eric Gaberman, partnering with the [Country Music] Hall of Fame did so much research on our time — and the sentinel turn of music in our generation — that I said yes.

[It's a] film coming with so much fact, and then he brings it into the present. Those that have a mindset more to try to do what they wrote and how they did it. And the "outlaws" was more or less a branding in a time that branding wasn't even known, and it stuck. So, it's been useful to a lot of new artists coming with new sounds.

Jessi Colter

*Jessi Colter. Photo: Chris Phelps*

You've lived through so many epochs in the music industry, When you look back on your decades in the industry — all the triumphs and losses — what do you think of?

Well, there have certainly been chances. Don Was ran into us at the Crazy Horse in Orange County. He showed up in the dark, and scared me because I didn't know who he was. While Waylon was doing the show, and he just talked a minute and said, "You know what, Jessi? The '70s were so much fun."

There was something about that that was the beginning of a lot, but it was the ending of something. It was a major turn with the University in Austin having been exposed to a lot of rock. So when Waylon and Willie came with their sound there, they reacted more like a rock group — Waylon did not cross boundaries in those days. You didn't do it. The companies wouldn't allow it.

So, it was an amazing procedure that took place and we were so glad to be part of it. Since then, it's kind of rolled with the punches, and Americana has gotten its feet.

And Shooter has been miraculous in some of the things that he's yielded already. But Waylon and he both don't go for prizes. They do help you, but you have to have that creative want to.

When he was 16, he didn't want a car; he wanted Pro Tools. So, he started early on his path and is doing great. He was a little before his time in performance and then working through being the son of Waylon Jennings, he worked through that and did great.

He loved his father dearly, and he now is a great spokesman for his father, which I love. But all in all, we'll just have to wait and see what's going to happen around the corner.

On You're The One, Rhiannon Giddens' Craft Finds A Natural Outgrowth: Songwriting

Kendrick Lamar GRAMMY Rewind Hero
Kendrick Lamar

Photo: Jeff Kravitz/FilmMagic


GRAMMY Rewind: Kendrick Lamar Honors Hip-Hop's Greats While Accepting Best Rap Album GRAMMY For 'To Pimp a Butterfly' In 2016

Upon winning the GRAMMY for Best Rap Album for 'To Pimp a Butterfly,' Kendrick Lamar thanked those that helped him get to the stage, and the artists that blazed the trail for him.

GRAMMYs/Oct 13, 2023 - 06:01 pm

Updated Friday Oct. 13, 2023 to include info about Kendrick Lamar's most recent GRAMMY wins, as of the 2023 GRAMMYs.

A GRAMMY veteran these days, Kendrick Lamar has won 17 GRAMMYs and has received 47 GRAMMY nominations overall. A sizable chunk of his trophies came from the 58th annual GRAMMY Awards in 2016, when he walked away with five — including his first-ever win in the Best Rap Album category.

This installment of GRAMMY Rewind turns back the clock to 2016, revisiting Lamar's acceptance speech upon winning Best Rap Album for To Pimp A Butterfly. Though Lamar was alone on stage, he made it clear that he wouldn't be at the top of his game without the help of a broad support system. 

"First off, all glory to God, that's for sure," he said, kicking off a speech that went on to thank his parents, who he described as his "those who gave me the responsibility of knowing, of accepting the good with the bad."

Looking for more GRAMMYs news? The 2024 GRAMMY nominations are here!

He also extended his love and gratitude to his fiancée, Whitney Alford, and shouted out his Top Dawg Entertainment labelmates. Lamar specifically praised Top Dawg's CEO, Anthony Tiffith, for finding and developing raw talent that might not otherwise get the chance to pursue their musical dreams.

"We'd never forget that: Taking these kids out of the projects, out of Compton, and putting them right here on this stage, to be the best that they can be," Lamar — a Compton native himself — continued, leading into an impassioned conclusion spotlighting some of the cornerstone rap albums that came before To Pimp a Butterfly.

"Hip-hop. Ice Cube. This is for hip-hop," he said. "This is for Snoop Dogg, Doggystyle. This is for Illmatic, this is for Nas. We will live forever. Believe that."

To Pimp a Butterfly singles "Alright" and "These Walls" earned Lamar three more GRAMMYs that night, the former winning Best Rap Performance and Best Rap Song and the latter taking Best Rap/Sung Collaboration (the song features Bilal, Anna Wise and Thundercat). He also won Best Music Video for the remix of Taylor Swift's "Bad Blood." 

Lamar has since won Best Rap Album two more times, taking home the golden gramophone in 2018 for his blockbuster LP DAMN., and in 2023 for his bold fifth album, Mr. Morale & the Big Steppers.

Watch Lamar's full acceptance speech above, and check back at every Friday for more GRAMMY Rewind episodes. 

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Tom Waits Songbook
Tom Waits

From left: David Corio/Redferns; Paul Natkin/Getty Images; Scott Gries/Getty Images; Richard E. Aaron/Redferns


Songbook: A Comprehensive Guide To Tom Waits’ Evolution From L.A. Romantic To Subterranean Innovator

As Tom Waits’ series of Island Records releases from the ‘80s and ‘90s are being reissued, take an album-by-album trip through the legendary singer/songwriter’s significant body of work.

GRAMMYs/Sep 20, 2023 - 06:44 pm

When Tom Waits warned on "Underground," the first song on his transformational 1983 album Swordfishtrombones, "there’s a rumblin’ groan down below," he very well could have been describing the artistic awakening that made him a legend.

Once an earnest yet good-humored singer/songwriter, Tom Waits is the rare artist in the past 50 years to successfully pull off something as radical as a complete artistic reinvention. A songwriter with a taste for the dark and grotesque as much as the theatrical, Waits has built up a catalog heavy on bizarre characters, morbid nursery rhymes, gruff junkyard blues and a uniquely unconventional take on rock music. And though it took some experimentation, trial and error and eventually getting married to arrive on the sound we hear today, he’s made a five-decade career of embracing sounds on the fringe and turning them into memorable melodies.

A Southern California native who got his start playing folk clubs in San Diego before relocating to Los Angeles in the 1970s, Tom Waits debuted as a relatively conventional singer/songwriter with a twinge of blues and jazz in his bones. And where his earliest records found him singing with more of a raspy croon, he adopted a vocal growl more spiritually akin to Louis Armstrong and Captain Beefheart. 

Waits never quite fit in alongside peers such as Jackson Browne or James Taylor. His instincts often pushed himself somewhere a little dirtier and darker, favoring tales of vagabonds and outcasts told with an inebriated sentimentality and irreverent humor. Throughout his decades-long career, the two-time GRAMMY winner never let go of the emotional honesty in his songwriting. 

Waits has joked that he makes two types of songs: grim reapers and grand weepers. The former became his staple sound in the 1980s after he married longtime creative partner Kathleen Brennan and began his decade-long tenure on Island Records, which still occasionally found him returning to the latter via less frequent but no less disarming ballads. 

What once was a songbook reflective of the bars and familiar streets evolved into surreal dens of iniquity and theaters of the grotesque. Waits' knack for storytelling and character development only strengthened over the years, even as his songs took more oddball and ominous shape. Swordfishtrombones' "Sixteen Shells from a Thirty-Ought Six" follows a hunter following a crow into a Moby Dick-like epic; spoken word standout "What’s He Building In There?," from 1999’s Mule Variations, prompts the listener to ponder who’s really up to no good. 

Though his record sales have been modest, Waits' songs have been covered by the likes of Rod Stewart and Eagles, and he’s collaborated with everyone from Bette Midler to Keith Richards. His songwriting and unique musical aesthetic have influenced records by Andrew Bird, Neko Case, Morphine and PJ Harvey.

As Waits’ acclaimed series of albums on Island Records from the ‘80s and ‘90s are being reissued in remastered form — some for the first time on vinyl in decades — revisits the legendary singer/songwriter’s significant body of work via each of his studio albums. Press play on the Spotify playlist below, or visit Apple Music, Pandora, and Amazon Music to enter Waits' sonic wonderland of '70s era  ballads and his plethora of twisted narratives and experimental sounds.

The Barroom Balladeer

Though often treated to his own idiosyncratic filter, Waits’ early output in the ‘70s reflected the glamor and sleaze of his Los Angeles surroundings. 

Closing Time (1973)

Making his debut at the height of the ‘70s singer/songwriter boom, Tom Waits revealed only slight glimpses of his myriad idiosyncrasies on 1973’s Closing Time. Heavily composed of ballads, the album’s sound is a result of a compromise between Waits’ own preference for more jazz-leaning material and producer Jerry Yester’s penchant for folk. 

Despite, or perhaps because of, that creative tension, Closing Time has a unique character. A sense of wanderlust and escape within its 12 piano-based songs feels like a jazzier, West Coast counterpart to Bruce Springsteen. Waits imbues the call of the road with a sense of melancholy on gorgeous opener "Ol’ 55" and gives a hefty tug at the heartstrings on the aching "Martha." He kicks up the tempo on "Ice Cream Man." Closing Time is often at its best when it’s more quietly haunting, like on the bluesy "Virginia Avenue."

Though the album didn’t initially garner much critical or commercial attention, it’s since become regarded as one of the finest moments of Waits’ early recordings. It also quickly earned the respect and admiration of other artists, with various songs from Closing Time being covered by Bette Midler, Eagles and Tim Buckley. 

The Heart of Saturday Night (1974)

After establishing himself with the romantic ballads of his debut album, Waits waded deeper into the waters of boho jazz and beat poetry in its follow-up, The Heart of Saturday Night. 

Waits shares his perspective from the piano bench and the barstool, occasionally delving into a sing-speak delivery against upright bass and brushed-drum backing. Throughout, Waits serves up colorfully embellished imagery about nights on the town and getting soused on the moon. Though not as experimental or sophisticated as some of his later recordings, The Heart of Saturday Night nonetheless finds Waits in a more playful mood, more overtly showcasing his sense of humor and penchant for a particular kind of down-and-out protagonist. Fittingly, the album's title track was directly inspired by Jack Kerouac.

The Heart of Saturday Night is somewhat autobiographical in that it’s one of the few albums that repeatedly features references to his youth growing up in San Diego. Most famously on "San Diego Serenade," as well as in his narrative of driving through Oceanside in "Diamonds on My Windshield," and his name-drop of Napoleone’s Pizza House, the pizzeria in National City where he worked as a teenager, in "The Ghosts of Saturday Night."

Nighthawks at the Diner (1975)

As Tom Waits further established himself as a singer/songwriter more at home in the naugahyde and second-hand smoke of a seedy nightclub than a folk festival, he sought to replicate the atmosphere of a jazz club on his third album. It’s not a live album in a literal sense; Waits invited a small crowd into the Record Plant studio in Los Angeles on two nights in July of 1975, and though the venue is artifice, the crowd reactions are genuine. 

More heavily rooted in jazz than Waits’ first two albums, Nighthawks at the Diner mostly follows a particular pattern: An "intro" track featuring some witty barfly banter, followed by an actual song. Introducing each song with a round of inebriated wordplay ("you’ve been standing on the corner of Fifth and Vermouth," "Well I order my veal cutlet, Christ, it just left the plate and walked down to the end of the counter…") is a bit of a gimmick, yet for all its loose, freewheeling feel, the album features some of his best early songs, including "Eggs and Sausage," "Warm Beer and Cold Women" and "Big Joe and Phantom 309." 

Releasing a manufactured live album early on proved a canny gambit for Tom Waits and resulted in his highest charting album up to that date. And it’s easy to see why: Nighthawks showcased the raconteur persona that’d come to define much of Waits' work to come. 

The Bluesy Bohemian

Embracing a grittier sound and a more character-driven approach to storytelling, Tom Waits entered a period of creative growth in the second half of the ‘70s that saw him balancing a darker tone with a wry sense of humor.

Small Change (1976)

On his second and third albums, a jazz influence and increasingly prominent humor saw Waits  developing not just as a distinctive personality, but as a character. His raspy growl deepened onSmall Change, as Waits'  barfly persona finds himself in increasingly seedier surroundings. This new area is  best showcased through the amusingly unsexy striptease scat of "Pasties and a G-String" and the surreal and misty eyed "The Piano Has Been Drinking."

Small Change isn’t nearly as jokey as the previous year’s Nighthawks at the Diner, but Waits carries a persistent smirk as he rattles through a laundry list of hucksterish advertising slogans in the carnival-barker beat jazz of "Step Right Up": "It gets rid of unwanted facial hair, It gets rid of embarrassing age spots, It delivers the pizza." He even ramps up an element of danger in the noir poetry of "Small Change (Got Rained on With His Own .38)".

Still, the heartache and romance remains within the album’s best ballads, including the gorgeous opener "Tom Traubert’s Blues" and the imagined depiction of a lonely waitress in "Invitation to the Blues." 

Foreign Affairs (1977)

Tom Waits’ fifth album Foreign Affairs unexpectedly became one of his most consequential releases. 

A rare Waits album that opens with an instrumental ("Cinny’s Waltz"), Foreign Affairs finds him taking on more narrative driven songwriting, as in the lengthy noir tale of "Potter’s Field" and the nostalgic road-movie recollection of "Burma-Shave." It seems fitting that this is the moment where Hollywood began to crack a door open for Waits — these songs sound like they were made for the silver screen. 

Indeed, album standout  "I Never Talk to Strangers," a duet with Bette Midler, inspired Francis Ford Coppola’s 1981 film One From the Heart. Waits wrote and performed on its  soundtrack, and would work with Coppola multiple times.

Blue Valentine (1978)

Parallels between Waits' music and his acting career crop up throughout , beginning with 1978’s Blue Valentine. Released the same year that he made his acting debut in Paradise Alley — cast as a piano player named Mumbles, an apt role to be sure — Blue Valentine opens with a big, cinematic number itself, Rodgers and Hammerstein’s "Somewhere," the famous ballad from West Side Story.

Blue Valentine also finds Waits in character development mode, increasingly populating his bluesy and bedraggled songs with widows and bounty hunters, night clerks and scarecrows wearing shades. It also features one of his most heartbreaking songs in "Christmas Card from a Hooker in Minneapolis," in which Waits’ first-person epistle comes from the voice of the title character who reaches out to an old friend in a hopeful and warm update on the changes she’s made for the better. And then he seamlessly, devastatingly pulls out the rug from underneath it all, as only a fabulist like Tom Waits can. 

Heartattack and Vine (1980)

The transition from one decade to the next couldn’t have been starker for Tom Waits as he entered the 1980s. His final album for Asylum Records seemed to signal a sea change, with its leadoff track steeped in scuzzy, distorted guitar and gruff blues-rock rather than piano balladry, jazz and beat poetry.

Heartattack and Vine is in large part more of a proper rock record than any of Waits’ earlier albums, as he lends his husky growl to gritty songs such as "Downtown" and "In Shades." Still, it’s the most tender moments that comprise some of Heartattack and Vine’s most enduring songs, such as "On the Nickel" and, in particular, "Jersey Girl," covered four years later by the Garden State’s own Bruce Springsteen. 

The Avant-Garde Auteur

Tom Waits underwent a significant transformation in the 1980s, mostly leaving behind the smoky jazz-club ballads of the ‘70s in favor of a more avant garde take on rock music, rife with an arsenal of unconventional instruments. 

Swordfishtrombones (1983)

The most dramatic shift in Tom Waits’ career came with the release of 1983’s Swordfishtrombones, his first release for Island Records and the first album of what came to be the sound most often associated with Waits. It’s rougher, rawer, more experimental and offbeat. A great deal of the credit goes to Waits’ wife, Kathleen Brennan, who introduced him to artists like Captain Beefheart and who became his creative partner, co-writing many of his best-known songs. 

Waits trades the piano and strings of his earlier material for arrangements better fit for junkyard jam sessions and New Orleans funerals. Though he’s delivered a long list of releases that have since usurped such a title, Swordfishtrombones certainly sounded like his weirdest album at the time. Very little of it sounded like a conventional pop song;it’s interwoven with spoken-word pieces both hilarious and unnerving ("Frank’s Wild Years," "Trouble’s Braids"), instrumentals ("Dave the Butcher," "Rainbirds"), boneyard bashers ("Underground," "16 Shells from a Thirty-Ought Six") and even a few tender ballads ("Johnsburg, Illinois," "Town With No Cheer"). 

Though arguably far less commercial than anything he’d released prior, Swordfishtrombones still cracked the bottom half of the album charts. It also received the attention of critics, who praised Waits’ bold new direction and unconventional stylistic choices. 

Rain Dogs (1985)

For much of the 1970s, Tom Waits took inspiration from the seamier side of Los Angeles, with occasional sentimental nods to his youth further south along Interstate 5 in San Diego. With 1985’s Rain Dogs, however, he relocated to New York City to capture an even grimier and grittier album inspired by its outcasts and outlaws. 

Recorded in what was then a rough part of Manhattan in 1984, Rain Dogs continues the stylistic experimentation of Swordfishtrombones with an unusual array of instruments for a rock album, including marimba, trombone and accordion, the latter of which opens the title track in dramatic fashion with an incredible solo.

Rain Dogs also began Waits’ long collaborative relationship with Marc Ribot, whose guitar playing helps craft the album's signature sound. Through his Cuban jazz-inspired playing on "Jockey Full of Bourbon" and the scratchy and dissonant solo on "Clap Hands." Yet the album also finds him in the company of Keith Richards, whose licks appear on the album’s most famous song, "Downtown Train," which became a hit for Rod Stewart when he covered it in 1991.

Rain Dogs features Waits’ first co-writing credit from Brennan, brought dded gravitas to the aching ballad "Hang Down Your Head." It’s one of a few moments that cuts through the carnivalesque atmosphere of the album (see the demented nursery rhyme "Cemetery Polka," the crime-scene poetry of "9th and Hennepin" and the litany of misfortunes in "Gun Street Girl"). IRain Dogs is Tom Waits perfecting his approach, completing a stylistic transformation with one of his greatest batches of songs.

Frank’s Wild Years (1987)

One of the highlights of Waits’ 1983 album Swordfishtrombones was a humorous spoken-word jazz interlude wrapped up in a David Lynch nightmare, titled "Frank’s Wild Years," in which the titular Frank settles down into a suburban lifestyle, only to set his house on fire and drive off with the flames reflecting in his rearview mirror. Those 115 seconds or so were enough for Waits and Brennan to spin the idea out into a stage play, with this album serving as its soundtrack. (Its original cast at Chicago’s Steppenwolf Theatre included Gary Sinise and Laurie Metcalf.) 

Frank’s Wild Years likewise comprises songs performed in the play, though without the context of knowing its origins, it doesn’t so easily scan as a set of songs written for the stage. It continues the aesthetic vision that Waits pursued on his two previous Island Records albums, steeped in Weill-ian cabaret and mangled lounge-jazz renditions, like in the hammy Vegas version of "Straight to the Top." Waits continues to run wild stylistically, however, veering from junkyard blues-rock in opener "Hang On St. Christopher" to the tenderness of the lo-fi 78-style recording of closing ballad "Innocent When You Dream."

Fifteen years after its release, "Way Down in the Hole," was given a second life as the theme for the HBO drama "The Wire," each season featuring a different artist’s rendition of the song. Waits’ original scores the opening credits for season two. 

Bone Machine (1992)

The title of Tom Waits’ tenth album fairly accurately sums up the sound of the record, which finds Waits incorporating heavier use of curious forms of percussion, many of them he played himself. Opening track "Earth Died Screaming" even resembles the sound of bones clanking against each other as Waits growls his way through an apocalyptic nightmare.

It’s fitting that Bone Machine coincided with Waits’ appearance as Renfield in Francis Ford Coppola’s Bram Stoker’s Dracula. A macabre sensibility and grotesque narratives permeate this record:Acts of violence become a form of entertainment in "In the Colosseum," and he retells an actual story of a grisly homicide in "Murder in the Red Barn." There’s levity too, like in the delusions of a fame-seeker in the rowdy "Goin’ Out West," which, along with half the songs on the album, was co-written by Brennan.  

Eerie and macabre as Bone Machine is, it earned Waits his first  GRAMMYAward, for Best Alternative Music Album in 1993. Likewise, the Ramones covered standout track "I Don’t Wanna Grow Up" three years later on their final album ¡Adios Amigos!; Waits repaid the favor in 2003 with a cover of the band’s "Return of Jackie and Judy." 

The Storyteller’s Songbook

Deeper into the ‘90s and ‘00s, Waits became more active in writing music for the theatrical stage, albeit filtered through his own peculiar lens. He also closed out the ‘90s with his longest album, helping to usher in a late-career renaissance. 

The Black Rider (1993)

The soundtrack to a theatrical production,The Black Rider closed Waits' tenure with Island Records with the soundtrack to a theatrical production. Though his music appeared in films by the likes of Jim Jarmusch and Francis Ford Coppola, and he entered the world of theater with Frank’s Wild Years, this was his released  composed in collaboration with playwright Robert Wilson — they would work on three productions together — based on German folktale Der Freischütz. In fact, Waits affects his best German accent in the title track, in which he beckons, "Come on along with ze black rider, we’ll have a gay old time!"

Highlights "Flash Pan Hunter," "November" and "Just the Right Bullets" juxtapose distorted barks against ramshackle arrangements of plucked banjo, clarinet and singing saw. , The structure of the album — rife with interludes, instrumentals and reprises — sets it apart from any of his prior works, leaving room for the listener to fill in the visual blanks. 

Mule Variations (1999)

The release of Mule Variations coincided with the launch of Anti- Records, an offshoot of L.A. punk label Epitaph that was more focused on legacy artists in a variety of genres. This also resulted in the unlikely instance of a song by Tom Waits appearing on one of Epitaph’s famed Punk-O-Rama compilations, which typically featured selections by the likes of skatepunk icons NOFX and Pennywise. 

The longest studio album in Waits’ catalog, Mule Variations makes good on a six-year gap by being stacked with an eclectic selection of songs, most of them co-written with Brennan (who also co-produced the album). From the lo-fi beatbox bark that blows open the doors of leadoff track "Big In Japan," Waits essentially takes a tour through a disparate but cohesive set of songs that feels like a career summary, from tent-revival blues ("Eyeball Kid"), to devastating balladry ("Georgia Lee") and rapturous gospel ("Come On Up to the House"). 

A new generation of TikTok users received an introduction to this album via a meme featuring the album’s "What’s He Building In There?", an eerie spoken-word track from the perspective of a paranoid, busybody neighbor that became an unlikely viral sensation. 

Blood Money & Alice (2002)

 Another collaboration with playwright/director Robert Wilson, Blood Money and Alice were released on the same day in 2002. Co-written by Brennan, both are the soundtracks to  two plays, the former based on an unfinished Georg Büchner play Woyzeck and the latter an adaptation of Alice in Wonderland

Blood Money is darker and harsher in tone, kicking off with the satirically pessimistic "Misery is the River of the World," and featuring highlights such as the obituary mambo of "Everything Goes to Hell" and the charmingly tender "All the World Is Green."

Alice — whose songs had been circulated for years in bootlegs in rougher form — is more subdued and strange, its gorgeously lush and haunting opening ballad an opening into a head-spinning world of Lewis Carroll surrealism and disorientation. "Kommienezuspadt" soundtracks White Rabbit hijinks through German narration and Raymond Scott machinations, "We’re All Mad Here" lends a slightly darker shadow to an uneasy tea party, and "Poor Edward" diverts slightly from Carroll canon to visit the story of Edward Mordrake, a man born with a face on the back of his head. 

The Catalog Continues…

Though Waits hasn’t been quite as prolific in the past two decades as he had been from the ‘70s through the late ‘90s, he continued to refine and evolve his strange and uncanny sound, while sharing a triple-album’s worth of rare material that offered a wide view of his evolution over the prior two decades.

Real Gone (2004)

Waits maintained his prolific streak with the lengthy Real Gone, which featured 16 songs and spans nearly 70 minutes — just a hair shorter than his longest, Mule Variations. It’s also the rare Tom Waits album to feature no piano or organ, its melodies primarily provided via noisier guitar from Harry Cody, Larry Taylor and longtime collaborator Marc Ribot, along with contributions from Primus bassist Les Claypool and Waits’ own son, Casey, who provides percussion and turntable scratches. 

Real Gone is, at its wildest, the most abrasive record in Waits’ catalog, clanging and clapping and clattering through uproarious standouts such as the supernatural mambo of "Hoist That Rag," the CB-radio squawk of "Shake It" and creepy-crawly stomp "Don’t Go Into That Barn," one of his better scary stories to tell in the dark. He leaves a little room to ease back on dirges like the haunting "How’s It Gonna End" and the subtly gorgeous "Green Grass," but every corner of the album is populated by outsized characters and ominous visions that seem larger than ever.

Orphans: Brawlers, Bawlers and Bastards (2006)

A career as long and fruitful as that of Tom Waits is bound to leave some material on the cutting room floor, the likes of which is compiled on the triple-disc set Orphans. Composed of non-album material that stretches all the way back to the 1980s, it’s divided into three distinctive themes: Brawlers, a disc of rowdier rock ‘n’ roll and blues material; Bawlers, a set of ballads; and Bastards, made up of what doesn’t fit into the other two categories — essentially Waits’ most fringe, peculiar music. 

In drawing the focus toward each distinctive type of songs, Waits lets listeners experience more intensive, discrete aspects of his music. It’s the "Bastards," however, that tap into the extremes of Waits’ unique talents, comprising strange and macabre storytelling, unintelligible barks, even a wildly distinctive take on "Heigh Ho," from Snow White and the Seven Dwarfs.

Some of these songs had previously been released in some fashion — many of them appearing on movie soundtracks as well as collaborative efforts like Sparklehorse’s "Dog Door" — Orphans  speaks to how productive he’s been over the past 40 years. 

Bad As Me (2011)

Tom Waits’ final album (so far) hit shelves 12 years ago, the aftermath of which opened up his longest stretch without any new music since he began releasing records. Yet Bad As Me only offers the suggestion that Waits still has plenty of energy and inspiration left in the tank, as the album — released when he was 61 years old — comprises some of the hardest rocking material he’s ever committed to tape. It’s an album heavy on rowdy rock ‘n’ roll guitar, including that of Keith Richards, who had also previously lent his guitar playing to 1985’s Rain Dogs, as well as longtime collaborator Marc Ribot and Los Lobos’ David Hidalgo. Waits mostly adheres to concise, charged-up barnburners such as "Let’s Get Lost," "Chicago" and the more politically charged anti-war song "Hell Broke Luce." Though when Waits does ease off the throttle on songs like the eerie "Talking at the Same Time," the results are often spectacular. 

If Tom Waits were to simply leave this as the end of his recorded legacy, it’d be a satisfying closing statement, though the closing ballad "New Year’s Eve" — ending on a brief round of "Auld Lang Syne" — would suggest new beginnings ahead of him. As it turns out, Bad As Me isn’t intended to be his last; earlier this year he confirmed that, for the first time in over a decade, he’s been working on writing new songs. 

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