Willie Nelson’s That’s Life

The Red Headed Stranger turns his gaze once again to Ol’ Blue Eyes

by Mikal Gilmore

The video for the title track from That’s Life features the painter Paul Mann creating the cover image, evoking classic Sinatra covers

When Willie Nelson sings “That’s Life” — the title track here, on his second collection of Frank Sinatra songs (the first, My Way, was released in 2018), he does something wholly unexpected: he makes the song philosophical, as in thoughtful. It goes against the grain of Sinatra’s original 1966 hit single version, which was also philosophical though more along how-to-live-life philosophical lines. The song, by Dean Kay and Kelly Gordon, hadn’t been written for Sinatra. Instead, it was aimed at Ray Charles, but Charles was taking his time about getting to it. Meantime, jazz and soul singer O.C. Smith made a middling hit version that Sinatra heard while driving in L.A. in 1965. He pulled over the car, listened, and immediately had a vision of how to perform it: like a Ray Charles song — hard blues with a sexy swagger. That’s how it sounded in his early 1966 single, as — over the accompaniment of a simmering, sexy Hammond organ — Sinatra roared out lines about all the ups and downs of life, the vicissitudes that sometimes knocked him on his ass but hadn’t yet killed him: “I’ve been a puppet, a pauper, a pirate, a poet, a pawn and a king/I’ve been up and down and over and out, and I know one thing/Each time I find myself flat on my face/I pick myself up and get back in the race.” It had more verve than anything else Sinatra recorded in the 1960s. He had taken a song about forbearance and made it exciting. He took a song in which he announced that “I thought about quitting” — meaning, well, suicide — with so much life (and humor) that it vaulted quickly up the pop charts, making №4. It was philosophical, as in: live life.

Nelson came at the song from a different angle — in a voice more weathered, looking back, reflecting: “You’re riding high in April, shot down in May,” he sings, more wizened than pugnacious, against a much more relaxed backdrop than Sinatra’s. “But I know I’m gonna change that tune/When I’m back on top, back on top in June.” He sounds like he’s seen plenty of Mays and Junes. His voice is full of memory. It recalls what it was like when people stomped on his dreams. He also accepts all the inconstancy and reversals; he’s kept faith with life, and with his good humor, but…well, that’s life. It takes determination, yet it leaves damage. Willie did something similar when he sang “My Way,” the title song on his first Sinatra collection, back in 2018. With that song, above any other, he knew he was treading into legendary territory — taking on the one piece of music most identified with the famed singer’s persona. Paul Anka had adapted the song from a French pop hit in 1968 as a valedictory statement for Sinatra, after the singer told him he was planning to retire. Anka crafted lyrics to serve the singer as a big-voiced, autobiographical brag: Sinatra was a man who lived by his own rules, without apologies or regrets. In Willie’s voice, though, the words sounded more rueful, more battle-scarred. His take afforded listeners a different insight into Sinatra, who had famously come to hate “My Way” over the years — sometimes saying so right before singing it on stage. In part that was to do its opening lines: “And now the end is near/And so I face the final curtain.” They’d once literally heralded the singer stopping performing in the early 1970s, but after he came back from retirement that lyric came to mean something different. It couldn’t always have been easy when, night after night, for well over two decades, Sinatra intoned those words to an audience that now understood them as a harbinger: death was getting nearer. There was no way he could recast the lyrics for a different meaning as he neared his 80s, and no way he could stop performing the song. For his part, though, Nelson didn’t try to recast the weight of those lines. There was mortality in his “My Way.” Which is how he made “My Way” his way — because there is always mortality in Willie Nelson’s voice.

“There’s no way to make these songs better than what Sinatra did with them,” says Buddy Cannon, who along with arranger Matt Rollings co-produced My Way and That’s Life. “But you can do it different. What we were shooting for was to try to make it feel like Willie had lived the lyrics. And he has — he’s lived both of those songs. When he sings them, he sings what they mean to him.”

Most Sinatra tribute sets come, of course, from artists who play or sing jazz or the repertoire of show tunes and twentieth-century Tin Pan Alley songwriters — that is, the pre-1960s American Songbook. They have a natural affinity for that body of standards, which Sinatra both drew from and helped to forever define. Which means that, as pleasurable as those sets may be, they don’t often produce something that surprises us. Willie Nelson, however, comes from the country music tradition. He’s as legendary in that genre as Sinatra was in his. Indeed, he has contributed substantially to the songbook that defines country music’s ethos, subject matter and emotional essence: songs about outlaws, songs meant to be played in honky-tonks, but most important songs about love — some that speak to the hope of how it might redeem an anguished heart, or that commiserate in the hours when anguish just won’t relent. Similar traits can be said to apply to Sinatra as well, both the man and the artist. He famously lived by his own rules, and for all his deep sensitivity as a vocalist he could also be a hellraiser. But the single thing Sinatra did best was to raise the art of romantic vocals to a new height, whether he was singing for people on the dancefloor or for the lone soul in a dark room, in the deep blue post-midnight hours. He called himself a “saloon singer”: that is, somebody singing as if he were holding a conversation — sometimes with a bartender, sometimes just with himself — about the stultifying woe he was left with when love walked out the door — for good. By comparison, Nelson could be called a honky-tonk singer, for the rough-and-tumble establishments he sang in for years, for the sound of much of his music — sometimes high-stepping, sometimes high-lonesome — and for the sort of stories his music often tells: tales of the other side of life, of heartbreak, unfaithfulness, remorse, of pain that drives the characters in his songs to drink. What Nelson does here on That’s Life — as he did on My Way — is find common ground with Sinatra. As a result, what binds these singers is an understanding that, regardless of genre, the art of both men is one and the same: giving voice to songs of experience. Nelson does here what Sinatra did with the original recordings: He treats each song as if it’s the inevitable expression of a personal experience, as if there’s no separating the singer from the emotion or meaning of the songs he sings, and therefore no separating the listener from the experience of a singular and compelling voice. Nelson doesn’t try to sound like Sinatra — he couldn’t. Instead, he comprehends him, and in doing so he deepens our understanding of both singers.

Willie and Diana Krall’s duet of “I Won’t Dance” from That’s Life

Willie Nelson’s affinity for Frank Sinatra’s singing was long in the making. In 1943, when he was ten, Nelson was living with his sister Bobbie in Abbott, Texas in their grandmother’s house when Sinatra joined Your Hit Parade, a weekly radio program, broadcast every Saturday evening. Nelson was already listening to the honky-tonk of Ernest Tubb and the western swing of Bob Wills and his Texas Playboys on radio, as well as the swing of Duke Ellington and Louis Armstrong. Sinatra was already on his meteoric rise and he had a singular sound that immediately caught Willie’s ear. “Though he was a million miles from western swing, he had a sweet swing of his own,” Willie later wrote in It’s a Long Story: My Life. “There was a tenderness to his voice, a purity and ease of phrasing. When he sang the popular songs of the day, I marveled at the natural way he told the story. When he sang with trombonist Tommy Dorsey, I heard how he used his voice like an instrument. And when Dorsey played his mellow trombone, I heard how he used his instrument like a voice.” Bobbie was two years Willie’s senior and had started playing piano at age five, taught by her grandmother. “I learned some of those Sinatra songs just sitting on the piano stool next to her, when she was probably 12,” he told me recently. “She was playing, reading music. Songs like ‘Stardust’ and ‘Moonlight in Vermont.’ That’s when I first got introduced to that music.” Later, as Willie adopted favorites among country singers, he found himself drawn to crooner-types such as Floyd Tilman and Ray Price, both whom he regarded as Sinatra peers.

Twenty years later — in the early 1960s — when Nelson was living in Nashville, establishing himself as a performer in honky-tonks and as a writer and singer in the studio, he had developed vocal traits that shared some ground with Sinatra’s style, particularly phrasing. “I’ve always admired Sinatra’s phrasing,” Willie told me, “He kind of did it like he wanted to. And that’s kind of the way I do it.”

First single “Cottage For Sale” was released in December just in time for Frank’s 105th birthday

Sinatra, though, ostensibly enjoyed more latitude for his way of singing because he emerged from jazz contexts that rewarded supple inventiveness. By contrast, Nelson was working in the country idiom which, like rock, expected singers to stay in the parameters of the beat. Some Nashville producers, such as Chet Atkins, couldn’t figure out how to accommodate his performance style. They thought his singing disregarded strict tempo — which it did: It would quicken or slacken, though without altering the overall pace. An exception was Tommy Allsup, a guitarist who had played with Bob Wills and Buddy Holly and who produced Nelson at Liberty. “He sang behind the beat,” Allsup once said, but he was always in meter.” he said. “That’s the way jazz singers sing.” But it wasn’t until Willie’s years at Atlantic Records, in the early 1970s, that he was met with jazz and R&B-oriented producers, Jerry Wexler and Arif Mardin, who gave his instincts full free reign. Buddy Cannon, Nelson’s mainstay producer, depends on the singer’s jazz instincts. “Willie’s ’s an improvisational musician,” he told me. “Why play and sing the parts over and over and over? It’s going to be different every time. Get a good one and go with it…. There’s no coaching Willie. It would take someone who doesn’t know what they’re doing, at least where he’s concerned, to go out there and try to tell him how to sing. When I first started listening to him that quality was part of what attracted me to him. His lyrics were one thing. But his method of delivering the lyrics — that offbeat, it’s funny, it’s so unthinkable. I see him sometimes chuckling at himself, at what he just did, because it’s not planned. He doesn’t plan to do that stuff most of the time.”

The other major quality that Nelson shared with Sinatra is something we hear throughout That’s Life, as we did on My Way: Willie leans in close and talks to us — tells us his story. That was something Sinatra was especially good at. It came with being a saloon singer. When he rebuilt his career in the early 1950s, after a period of personal crisis, he also rebuilt the heart of his artistry. His new delivery sounded guileless and “easy,” even colloquial — meaning his phrasing and intonation seemed to spring as much from the rhythms of speech as from the cadences of melody. As a result, his vocalizing served to heighten the emotional and thematic intent of a song, and make its lyrics seem like nothing so much as a word between friends. Sinatra was the voice of a man alone in a room with the listener — or even alone in a room, talking to himself. Willie came naturally to that sort of close rapport with a listener. His ability to dwell on the recollection of a final farewell in “Blue Eyes Crying in the Rain,” from 1975’s Red Headed Stranger, proved such an intimate yet powerful rumination that it established him straight away as an authentic and major voice. Three years later, he brought that same up-close manner to the neighborhood of Sinatra with Stardust, a collection of evergreen standards — some by American Songbook writers Irving Berlin, George and Ira Gershwin, Hoagy Carmichael and Duke Ellington — rendered moodily, like ghostly memories that visit a solitary listener after midnight. Nelson’s label, Columbia, worried that an album of low-key torch ballads would muddle Nelson’s standing as a prominent figure in country’s still-strong Outlaw movement, effectively costing him his guaranteed audience without attracting any other wide listenership. “It was definitely different from what we had been presenting to the fans,” says harmonica player Mickey Raphael, who has played with Nelson since Red Headed Stranger. “But it was the American Songbook, and these were songs that Willie had grown up with. Who can argue with any of those songs?” As it turned out, nobody. The album went on to be the biggest seller in Nelson’s career, and proved eventful in other unforeseen ways. Willie Nelson singlehandedly established that Tin Pan Alley- and jazz-derived songs could still prove timely and affecting to a vast and vital audience of diverse constituencies. Stardust drew a twentieth-century line that ran from blues and jazz to country and pop in ways nobody else ever had, yet did with modesty and economy. It was a lonely work, not an orchestral blowout, but its seemingly limited scope in fact embraced everybody. If Red Headed Stranger had marked him as a major serious artist, Stardust made him universal, for all time, a voice that brought the past unexpectedly into the present. As a result it also established Willie Nelson as the most popular interpreter of standards since Sinatra himself.

Stardust eventually drew Sinatra’s attention. In 1984 casino operator Steve Wynn was booking the Golden Nugget’s Theatre Ballroom when he went to visit the singer in Palm Springs, California with a proposal: He wanted to schedule Sinatra and Nelson on the same bill. He had brought along Stardust and Electric Horseman and played, among other tracks, Willie’s spectral-sounding “Moonlight in Vermont,” which Sinatra had also sung on 1958’s Come Fly with Me in one of his most ethereal recordings. “That cat can sing,” Sinatra told Wynn. “That cat’s a blues singer. He can sing my stuff but I don’t know if I can sing his.” Wynn made the booking, but as it turned it was Sinatra who opened and Nelson who headlined. “I don’t say that to brag,” Nelson later wrote. “Wasn’t my idea. It was Steve’s. He felt that since I was selling more records than Sinatra, I’d be a bigger draw and was entitled to top billing. I would have been happy with second billing, though. As I told Steve, Sinatra’s my favorite singer.” When Willie met Sinatra before the show he was surprised when he said, “You’re my favorite singer, Willie.” A short time later, though, Sinatra had to cut his performance short when a small vein in his throat broke. He couldn’t continue the dates but he waited backstage until Nelson finished. “He came to me afterwards,” Willie recalled, “and wanted to know if I’d come by his house and hang out a while. But I had to go somewhere, so I had to jump on the bus. I always regretted that.”

Frank Sinatra and Willie Nelson’s PSA for the Space Foundation

Months later, though, the two singers got to spend time together when they teamed up to make PSAs for the Space Foundation about aspects of how the program could benefit hospital treatments. At one point, Sinatra — bemused by Willie’s down-home style — pointed at his headband and said, “What do you call that, Willie?” Nelson smiled and said, “I call it ‘my way,’ Francis.” Sinatra smiled back. “Touché,” he said. (Willie’s late stage manager, Poodie Locke, reportedly claimed that Sinatra once considered recording an album of Nelson covers.) In 1994 Nelson sang with Sinatra on the singer’s final album, Duets II, swapping lines on a spry performance of George and Ira Gershwin’s “A Foggy Day.” (Nelson recorded another rendition on My Way.) Then, in 2013, Capitol issued a twentieth anniversary set with an additional 1994 duet, “My Way,” that managed to realize all the song’s claims and contradictions. In it, Sinatra at last met the opening lines — about a final curtain — with a quavering voice that betrayed apprehension. Nelson followed with a confession that sounded demure rather than high-handed — “Regrets, I’ve had a few/Then again, too few to mention.” Sinatra closed the duet with the most adamant voice he ever brought to the song’s creed of self: “For what is a man, what has he got?/If not himself, then he has naught,” he almost shouted in brassy, strident tones, at age 79, as Willie joined him for the final proclamation: “The record shows, I took all the blows/And did it… MY WAY.” Sinatra died four years after those sessions. When Nelson returned to the song in 2018, it was a sympathetic contemplation: There had been pain behind the pride in the song.

In the 43 years since Stardust, Nelson has recorded numerous other Sinatra songs — mainly on subsequent standards collections, though until My Way he hadn’t made a fully Sinatra-centric set. When asked at the time why he finally took on the task, Nelson said, “I’d been wanting to do it for a long time. I’m 85 years old. If there’s any better time to do it, I don’t know! I think My Way is a pretty good time for an old guy to start singing.” As it turns out, My Way and That’s Life have a considerably different sensibility than any of Willie’s prior American Songbook forays, with an important exception: Summertime: Willie Nelson Sings Gershwin, from 2016, which provided Nelson’s sound with a new fulcrum, due to the creative team he worked with. In 2015, Willie was awarded The Library of Congress Gershwin Prize for Popular Song, an honor that “celebrates the work of an artist whose career reflects lifetime achievement in promoting song as a vehicle of musical expression and cultural understanding.” Prior recipients had included Paul Simon, Stevie Wonder, Paul McCartney, Burt Bacharach and Carole King, but interestingly none had the same depth of knowledge of George and Ira Gershwin’s songwriting tradition — that understanding of the American Songbook — that Nelson possessed. When Nelson and Buddy Cannon learned of the award, they decided it would be a nice tribute in return to record an all-Gershwins album. “I thought, ‘Holy crap! I want to do it,’” said Cannon, who has produced and co-written much of Nelson’s music in recent years (including the outstanding mortality suite of God’s Problem Child, Last Man Standing, Ride Me Back Home and First Rose of Spring). “But it was a little bit out of my wheelhouse, you know? I felt I could use some help with such a project. That’s when Matt Rollings came to mind.” Rollings is a Nashville sessions keyboardist, deeply schooled in jazz, known for his work in Lyle Lovett’s Large Band. He has played for Bruce Springsteen, Mavis Staples and Mark Knopfler; toured with Alison Krauss; produced Keith Urban and Mary Chapin Carpenter; written songs for Keith Urban, Randy Travis, Indigo Girls, Trisha Yearwood, Clint Black and Roberta Flack; and made eclectic albums of his own (Balconies and Mosaic);. “He was into the idea big time,” said Cannon.” Rollings arranged all the songs and assembled some extraordinary musicians: bassist Kevin Smith, drummer Jay Bellerose, upright bassist, David Piltch, guitarist Dean Parks, steel guitarist Paul Franklin and harmonica player Mickey Raphael. He also provided piano, Hammond B-3 organ, and Wurlitzer organ himself. It proved alchemical, as if they’d been playing after hours swing sessions for a lifetime in small settings — maybe saloons, maybe honky-tonks. Willie is famously a one-take singer, yet every one-take on Summertime felt careful and lived-in. In 2017 the album won a Grammy for the Best Traditional Pop Vocal Album.

Nelson followed Summertime with another tribute — this time to singer Ray Price (a friend who died in 2013 and, to Willie, a country counterpart to Sinatra) — then began work on the mortality cycle. By the time he and Buddy Cannon had finished Last Man Standing in late 2016, Willie decided to extend the standards paradigm of Summertime with the same team. He originally considered a collection of Broadway showtunes, but Cannon had noticed a trend: Every time they considered a song for the project, Willie said, “Send me Frank’s version.” He had done the same when choosing titles for Summertime (Sinatra had also sung eight of that album’s eleven selections). Nelson realized it was time to make the album he’d been circling around for over forty years. Of course, a Sinatra survey opened up different prospects — musically, emotionally and thematically. Especially thematically. Sinatra had pretty much invented the concept album. Starting with In the Wee Small Hours in 1955 and through She Shot Me Down in 1981, he recorded about 40 thematic works, alternating between sexy, uptempo, big-band-style dance affairs and brooding reflections on romantic despair. (Sinatra biographer James Kaplan commented: “That was Frank; he could make you want to die, and he could make you want to live.”) Willie Nelson, however, is the other great master of the concept album in popular music. Actually, you could call him the greater master: Starting with Yesterday’s Wine in 1971, Nelson has recorded over 75 thematic full-length works — some that unfolded as a narrative (Phases and Stages, Red Headed Stranger), others that focused on styles or ideas, or paid tributes. Some even took their themes from a single-worded title (Spirit and Heroes.) When it came to the Sinatra collections, Willie focused on two concepts: Sinatra himself and how he wanted to perform the singer’s music — that is, how he has located himself in the songs. On That’s Life the result has made for a remarkably diverse mix of the iconic (the title song and “I’ve Got You Under My Skin), the playful (“Nice Work if You Can Get It” and “Luck Be a Lady”), the affectionate (“I Won’t Dance” and “Just in Time”) and the disconsolate (“Cottage for Sale” and “In the Wee Small Hours of the Morning”).

In contrast to Summertime, horns and strings appear here, surrounding jazz cadences and country steel guitar solos. Rollings’ arrangements cut their own path on That’s Life; he has clearly listened to what Nelson Riddle, Neal Hefti, Billy May and Gordon Jenkins did in the 1950s and 1960s — there are allusions and quoted motif — throughout, but these are new sonic readings. “We never talked about sticking close to the originals,” Rollings says. “I listened closely to everything, but I’m not a fan of being derivative. I wanted to find how a song was written harmonically, what was the original intention, because a melody can work over a lot of different chords. Once I had that in in my head, I felt we had license to make it our own. After every arrangement I’d take it to Buddy. A lot of what makes this collaboration work so well is he has such a deep relationship with Willie, and he knows Willie so well, much better than I do. I call him ‘The Willie Whisperer.’”

“I’ve Got You Under My Skin” on the current album is a key example of what Rollings means when he talks about deconstructing a source arrangement. Sinatra’s version of the Cole Porter tune on his 1956 landmark album Songs for Swingin’ Lovers is a milestone moment in his career for how he and Nelson Riddle forged tension and dynamics, orchestra and voice, into one of the great popular music creations of the twentieth-century. Sinatra rode the song’s mounting momentum as it cascaded from a bluesy, pulsing sway into the biggest horns-and-drums rave-up that Riddle ever achieved on record, before the singer closed the song out with a cascading roar that dropped into a smooth lilt. The version here doesn’t try to reinvent the wheel, but instead puts its own spin on it. Rollings opens the track with Latin-accented figures played boldly in his piano’s low register. In lieu of Riddle’s impossibly big horn fanfaronade there’s a sly jazz guitar and country harmonica turn before Willie finishes out with stunningly timed phrasing, as he sing-talks through what just might be Porter’s most deft verse, making small lyrical revisions along the way: “I would sacrifice anything come what might/For the sake of having you near/In spite of a warning voice that comes in the night/And repeats, how it yells in my ear:/‘Don’t you know, you fool, there ain’t no way to win?/Why not use your mentality, wake up to reality’/And each time that I do just the thought of you/Makes me stop (and here lands Willie lands on the word in a way that acts it out) before I begin/’Cause I’ve got you under my skin/And I want you/And I need you/Under my skin.”

Willie also brings a twist to Jules Styne, Betty Comden and Adolph Green’s “Just in Time.” On Sinatra’s 1959 Come Dance with Me! (which won the Grammy for Album of the Year and remained on Billboard’s pop album chart for 140 weeks), Billy May arranged the song to fit the singer’s cool bearing. “Now you are here, and now I know just where I’m going/No more doubt or fear ’cause I’ve found my way,” he sang with romping horns behind him, making plain his doubts and fears were indeed well behind him. Here, Nelson sings the words against a relaxed shuffle swing — “Before you came my time was running low/I was lost, the losing dice were tossed/My bridges all were crossed, nowhere to go” — in the voice of somebody who remembers what it was like to be at the end of his rope, and now feels relief perhaps more than triumph. In other words, just as he did in “My Way,” Willie Nelson reveals the pain that had preceded the deliverance.

Sinatra, of course, was no stranger to that kind of reflection, in both song and real life. At its most profound, his singing portrayed a painful rumination that the singer needed to proclaim to himself in order to work his way free of a bitter memory. Willie has chosen two of Sinatra’s most indelible exemplars of the brokenhearted song: “Cottage for Sale” and “In the Wee Small Hours of the Morning.” The latter — a 1929 song by Willard Robison and Larry Conley — is about a loss that can never be healed: A man returns to a home that had once been “a little dream castle,” but the only thing it holds now is absence. The imagery is detailed: “The lawn we were proud of/Is waving in hay/A beautiful garden/Has withered away/Where you planted roses/The weeds seem to say/A cottage for sale.” Gordon Jenkins’ score on 1959’s No One Cares was funereal, and Sinatra’s voice was achingly beautiful yet hushed and doleful (Sinatra called No One Cares and an earlier album with Jenkins, Where Are You?, his “suicide albums).”Cottage for Sale” is a song that needs to be played close to the bone and Nelson makes its reverie of loss palpable. “From every single window,” he sings against strings, in a voice as softly plaintive as Sinatra’s, “I see your face/But when I reach the window/There’s empty space.” We are in that space with him and we can’t look away as he reads a notice: “The end of our story/Is there on the door/A cottage for sale.” Says Rollings: “It’s such a simple read, but it breaks my heart. It absolutely does. I can hear all of it in his voice. He doesn’t need to play the meaning. He’s just telling the story. The approach is the same as Sinatra’s. He sang the melody and found a rhythmic phrase that was conversational. That’s what he did that was so brilliant. You never heard phrasing with Sinatra — he didn’t make a point of — even though he was a master. It just sounded like he was talking to you. I think the same holds true for Willie.” Buddy Cannon adds that “Cottage for Sale” is perhaps his favorite track on the album. “To me it sounds like Hank Cochran could have written it,” says Buddy Cannon, thinking of the Nashville songwriter who was one of the first to call attention to Willie Nelson’s talent. “Or Willie could have written it. You know? Everything about that songs fits in any kind of genre you want to stick it in, especially a country song. I mean, it’s a beautiful country song.”

“In the Wee Small Hours of the Morning” is, in some ways, That’s Life’s greatest risk because Sinatra’s rendition seemed incomparable. The song was the last entry to find its way to Sinatra’s first blue concept album, in 1953, and it arrived accidentally. Sinatra and Riddle ran into Dave Mann and Dave Gilliard — two writers they knew — at 55th Street and Broadway in New York, as the singer and arranger were on their way to Capito. They were looking to settle on one final composition to fill out the heavy-hearted collection. Mann and Hilliard said they had just composed something late the night before. Sinatra invited them along to play the song for them. As they did they handed Sinatra the lyric sheet to “In the Wee Small Hours of the Morning.” He read through it, folded the sheet, put it in his pocket and said, “Fellas, this is my kind of song.” A few days later Capitol called Mann to tell him Sinatra had already recorded the song and was adapting its title as the album’s as well: In the Wee Small Hours. Sinatra never made a lovelier or more desolate work, and never recorded any song that better fit those terms than “In the Wee Small Hours of the Morning.” He must have known that because, if he ever performed it live, I haven’t found record of it. It isn’t that “In the Wee Small Hours of the Morning” is untouchable, it’s just that it’s never been touched with the same authenticity of dejection that Sinatra brought to it when he sang it at a time when he was living inside that experience. It hasn’t been touched that way…until now.

Sinatra sang it as a virtual throughline — even the strings interlude seemed to emanate from the brooding of a man who lies awake as the world sleeps. He thinks of nothing but the woman he has lost, maybe because he hurt her. Here, Willie is even closer to a song’s marrow than he was on “Cottage for Sale.” There is a presence in the room with the man’s thoughts as he implores his own thoughts: “When your lonely heart has learned its lesson/You’d be hers if only she would call/In the wee small hours of the morning/That’s the time you miss her most of all.” But it’s the presence of a void. When Mickey Raphael plays his harmonica, taking the place of the strings that flowed out of the singer’s mind in Sinatra’s recording, the lament plays from inside that void. (“I’m playing chromatic on that,” Mickey says. “That’s not my first instrument — I even took lessons then wrote out the passage and transposed it to the harmonica. I practiced that for a month. It was special to me. I wanted it to be right.”) Willie is mesmerizing here, looking into that void where the one thing he could not afford to lose has now slipped. But he’s also raw. Part of what made Sinatra’s skill with heartache so effective was how he sublimated those emotions into his brandytone voice. I don’t know whether Nelson has ever known the pain of this song as Sinatra knew it (and it’s none of my business), but I know he has the sensibility to locate that pain here. I once asked Buddy Cannon about where Nelson’s fellowship with the hurt in his songs came from — a lifetime reserve of knowledge or loss? “We would never talk about this stuff,” says Buddy Cannon, “We just never have done that We kind of write whatever the feeling is, or the sadness that is floating around us. If you’ve ever been wounded, emotionally, I don’t think that memory ever goes away. It kind of sneaks back in on you every now and then. It’s just reflecting, reflecting on stuff.

“Willie knows what he’s singing about,” says jazz pianist and vocalist Diana Krall, who duets here with Willie on “I Won’t Dance,” by Jerome Kern and Dorothy Hughes. “He understands the story, and that’s the means of telling it: through those words. When they sent me That’s Life, the songs were out of order, so ‘In the Wee Small Hours of the Morning’ was the first song that came on. I was in the kitchen with Elvis [Costello, Krall’s husband] and I went, ‘Hang on! Everything’s just all gone goosebumps’ — and I started… to cry, because, the way he was singing it — it’s a whole other level of experience and understanding. Sometimes we need to have people who understand that. Some of these songs talk about loss. Listening to them can bring you into a memory, and maybe that can help you: It becomes your story. Willie and Frank can do that. It’s also in their sense of time — they find that one note, and you just hang on. It’s mind-blowing artistically.”

The first time that Krall heard Willie Nelson was Stardust. She was fourteen and would soon be playing in a student jazz group, in British Columbia, Canada. “I got very, very into that record,” she says. “I’m still finding things that he’s done.” Over four decades later, Krall has seventeen acclaimed vocals-and-piano albums of her own, has sold over 15 million albums worldwide, has won three Grammy Awards, played on Paul McCartney’s Kisses on the Bottom (2012) and is widely regarded as one of the leading figures in jazz and vocal jazz. She first sang with Nelson on April 2009, at New York’s Beacon Theater, on the occasion of a TV special celebrating Willie’s 70th birthday. She and Costello joined him on “Crazy” — the jazz-inflected song he’d written for Patsy Cline, who first balked at it, then in 1962 it became one of her biggest hits. Diana sang the first verse and proved indeed that some can sing about loss in such a way we find ourselves in. “It was last-minute,” she says. “We were in the audience and got the invitation: ‘Why don’t you come up and sing with us?’ I’m super shy so I probably was freaking out, but Elvis is always good. ’Come on let’s do it!’ That was the first time I sang with Willie. It was very spontaneous. I thought I was probably out of my depth.” Apparently not, because Willie invited the pianist to sing with him on 2009’s American Classic, for “If I Had You,” a song Sinatra had also recorded a few times, most famously in a genial version on. 1957’s A Swingin’ Affair! Nelson and Krall’s version, though, sounded like a confidence, a nocturne in duet form, the two voices up close, with piano and upright bass.

Their take on Kern’s “I Won’t Dance” is also up close — at least virtually, because Nelson and Krall couldn’t sing in the same room due to the 2020 coronavirus. But the performance achieves the necessary intimacy for an exchange that is also a tease. In Sinatra’s version on A Swingin’ Affair!, it was a head-over-heels entreaty of a man who is afraid that if he gets close enough to dance with the woman he’s inveigling, he won’t want to dance because he’ll have other things on his mind: “You know what? You’re lovely/Ring-a-ding-ding, you’re lovely/And oh, what you do to me.” Hearing Sinatra’s beguiling delivery you knew his voice alone was enough to win him what he longed for. A different interaction is at work in Willie and Diana’s duet. Willie sounds like he’s truly giving both parties an honest caution, but Krall brings her own wit to bear. She recalls: “They didn’t give me any direction — ‘Here it is: Do what you want.” She was pleasantly surprised. “I said, ‘Give me a second. I’m just going to close my eyes and figure out what comes to my mind here.’ I figured, well, if I completely humiliate myself, don’t worry about it. We can just erase it.” Things move fast in the song — horns jab the air; Willie’s the stoic romantic; Diana, the character in control — but there’s an unexpected turn, though you might have to listen closely. “The producer told me,” says Diana, “‘Whatever you hear. Whatever you like. Go ahead.’ Willie’s not there with me in the room. I’m in Vancouver, I’m overdubbing this… ‘What am I going to do?’ Then, it all fell into place. I thought, well, just change the direction of the tune by saying, ‘Oh, you will dance with me.’ It ended up working because Willie left me all that space.”

“Diana did not mail it in,” says Buddy Cannon. “She did some really cool stuff to go with what Willie had done — really inventive.” I mention that, like Willie and like Sinatra, Diana Krall has her own singular sense of timing. It makes her duets with Nelson warm yet unpredictable. “It’s freedom,” replies Buddy. “Freedom. Diana has that when she sings and plays. And if I had to describe Willie Nelson’s voice in one word, it would be that: freedom.”

“She has an incredible voice,” Willie tells me, “and I’ll sing with her every chance I get.”

On February 25, 1995, Frank Sinatra gave his last public performance, at the invitation-only Frank Sinatra Celebrity Invitational gala in Palm Desert. It had been tradition for Sinatra to sing one or two songs, then send everybody off to the bar. He was 79. “I’m glad to be spending the evening with you,” he told the audience at the Marriott Hotel, “because it would be lonely in a saloon, just me.” He sang five songs — all had been in his live repertoire for decades; all had been showstoppers. Willie Nelson and his band played the same show. “It was great to sit on the stage and watch him,” says Mickey Raphael. “After he did a song, some of the guys there would go, ‘One down, four to go.’ It was like a countdown. It was really the end.” There had been some trepidation among Sinatra’s own band. The singer had at times been confused on stages during the prior tour. In Japan one night he had trouble remembering which song he was singing. Also, he was older as a singer now — there was a more vibrato evident when he held notes. That night in Palm Desert he avoided his strongest suit, ballads, likely because they showed more wear in the lower range of his baritone. Instead, as his son Frank Sinatra Jr. conducted the singer’s orchestra, Sinatra sang hard-hitting big band material that displayed his still magnificent fortissimo and enunciation.

Among the last songs Frank Sinatra sang for an audience was “You Make Me Feel So Young,” a 1946 song by Josef Myrow and Mack Gordon that he’d first performed on Songs for Swingin’ Lovers, where arranger Nelson Riddle turned it into a proclamation of ecstasy. Over the years, Sinatra had directed the song at his audience as a declaration that their love for him kept him vital. That night in Palm Desert, amid a blaring sashay of horns, Sinatra rendered the moment as an exclamation of rejuvenation: “You.Make.Me.Young.” On that night, in those minutes, with those words, he made good on that claim, just before retiring for good, before the final curtain fell dark.

Nelson Riddle is, of course, a hard act to follow, but Matt Rollings’ revision of “You Make Me Feel So Young” is perhaps even more adventurous. It opens with angular horn lines that curl and surround Nelson before he briefly quells the heat with some subdued guitar riffs. Willie finds in the lyrics the same avowal that Sinatra did, though perhaps he directs it at his vocation itself. Singing has given these men purpose and meaning even beyond the songs’ subject matter — the stories, the lessons and morals, the sustenance, consolation, fortitude — found in the lyrics. Certainly, Frank Sinatra became rich enough to live in any world he wanted to build for himself, and Willie for that matter has a whole little town — Luck, Texas — he could retire to if he wanted. But he doesn’t show signs that he sees his future that way. There’s an intrinsically heartening — if unexpected — emotional element about an 87 year old man singing: “You make me feel so young/You make me feel there are songs to be sung/Bells to be rung/And a wonderful fling to be flung/And even when I’m old and gray/I’m going to feel the way I do today/Because you make me feel so young.” It’s neither a vain boast nor wishful thinking. Right now, Nelson misses being on the road, but he and Buddy Cannon are busy preparing new material. Also, Nelson told me he might not be done with his exploration of the American Songbook — though he has a broader definition than some of what constitutes that catalog: “I’m sure somewhere down the road I’ll do another set of my favorite songs, which would be anything from Frank Sinatra to Hank Williams.”

Earlier I mentioned the mortality cycle that Willie and Cannon created in recent years and its songs about heartbreak, memory and courage, with love and loss as the great levelers. Summertime, My Way and now That’s Life amount to an equivalent cycle of storytelling. These songs — Frank Sinatra’s and Willie Nelson’s — tell us stories not only about the singers being up and down, over and out, flat on their faces, then picking themselves up and getting back in the race. As Diana Krall noted, we find something of ourselves in these stories as well, in the kinetic poetry of songs that embolden us throughout our lives, as long as they’re sung in the right voices.

Sony Music's catalog division. The deepest and richest music catalog in the world.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store