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In the 80s when I was a young teen, I fell for Sinatra while watching rented videos. I swooned when played young and vulnerable next to the cocky Gene Kelly in films like On The Town. Later I found those Capitol albums and learned from Sinatra about the great joys of falling in love and the great sorrows of heartbreak. I listened to the songs and wallowed in my own joy and my own pain. The ego you describe was there, and it may have encouraged my own. But great tenderness was there too. There are many irreplaceable interpreters of the American songbook, but I can't get over that rich, human baritone that brought such a thoughtful, subtle storyteller's inflection to each lyric. Seeing him interviewed in Carson clips or play bold and brassy in rat pack movies, I understand why many recoil from the persona. But I can't forget the beauty he created either. Artists, like the rest of us, are complex human beings. It's hard to make room for how messy that is. Thanks for a thoughtful essay that puts his boldest and brassiest hit in thoughtful context.

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No Sinatra fan here--to me he is all smoke and no substance. He's a wanna-be tough guy who is actually a lifelong Mama's boy. Piscopo imitated him, and didn't need to exaggerate in the least, singing flat and lifelessly--and nailing it. I'll listen to the genuinely talented Tony Bennett, Ray Charles, or Dean Martin instead. Oh yeah, 'New York, New York' belongs to Liza, who understands the lyrics aren't about the singer, but the city itself.

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Feb 6, 2022Liked by Ted Gioia

Ted, you should listen to "Watertown," his common guy/downwardly mobile/romantic loser album from around 1970. The music isn't particularly distinguished; instead of James van Heusen writing much of a new album for him, he had a couple of guys named Bob Gaudio and Jake Holmes. The liner notes don't tell the reader exactly how the Gaudio/Holmes team worked, so I don't know who should get the principal or entire credit, as the case may be, for the lyrics, but they are extremely moving in a way nothing else Sinatra ever sang was. The entire album is extremely moving in a way none of Sinatra's other heartbreak albums came close to being.

It's more than a concept album. I think of it more as a story album. The narrator's much loved wife has left him and their sons behind in Watertown, implicitly taking off with a lover. The cover drawing makes Watertown look like the sort of place which was the location of the first scenes of hundreds of Hollywood movies made during The Golden Era, in which, whatever the story, the main character, desperate to escape Nowhere, USA, catches the train for The Big City. ( New York, New York, maybe? )

But the narrator isn't going anywhere. He's a man of responsibility. He's going to raise their sons. Toward the end of the album, he thinks she may be coming back to him.

I think "Watertown" is a great work of art. It's the sort of thing I can imagine might have been written for Glen Campbell. I don't know much about its genesis, but my impression is that Sinatra commissioned its creation. I know he had strong hopes for it, and was hurt by its failure to catch on at all. If I'm not mistaken, one of his daughters said its failure was the deepest artistic hurt Sinatra ever suffered.

I think of it as his attempt to do penance for "My Way," a song which he seems to have despised. If you haven't heard "Watertown," you should.

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After listening to Sinatra attentively, closely, repeatedly I find that his ego yields to the demands of his art. Like many artists (especially those falling within the "romantic" tradition--e.g. Shelly, Keats, Byron, Schubert, Schumann) Sinatra in his life had many warts, deformities, unpleasantries. He also left a legacy of genius--but not in the sold-out concerts ending with "My Way" and not in latter-day singles like "Strangers in the Night." It's in the all-ballad albums--in which he and his symbiotic partner Nelson Riddle take popular music into regions of the heart normally reserved for artists like Shakespeare, Verdi, and Faulkner--that Sinatra touches us in ways both sublime and enduring.

No arranger-orchestrator had done anything like it before or since--not even Nelson Riddle on the albums he made with Nat Cole or Rosemary Clooney. The titles alone are indicative of their content's direction--"In the Wee Small Hours of the Morning," "No One Cares," "Only the Lonely" and a dozen more. Sinatra was unafraid (perhaps betraying some of that ego) of taking popular music into the darkest places of the human psyche--not excluding growing old and facing death.

The music created by Sinatra and Riddle transports the listener into the darkest depths and, ironically, the transcendental heights familiar to any reader of "King Lear" and the tragic grandeur of its completely stripped and naked protagonist. Or his ballads, which he sometimes referred to as "suicide songs," strike a chord familiar to the reader of the 2nd chapter of "Sound and the Fury," with its protagonist, Quentin Compson, mentally rehearsing the history--both his family's and the South's-- that had pushed him to this reactionary extreme of self-annihilation.

The songs of "Only the Lonely" are book-ended by two numbers featuring the piano (its only appearances on the album). The first number, composed specially for the session, is a formal Romantic theme with the piano promising an elegant concert to please all fans of Tchaikovsky's popular concerto. The final number is a bar-room piano, in which the vocalist descends from Orchestra Hall to the saloon, for Harold Arlen's "One for My Baby." It's the 8 songs making up the primary text of the album on which voice and orchestra share a journey unlike any other in American popular song. Starting with "Angel Eyes" and running through "Ebb Tide" is the insistent journey of the voice, as it surges in intensity, then drops down to barely overheard whispers, both leading and following the dynamic turns of the orchestra. Riddle's instrumentation rejects static, syrupy strings in favor of multiple choirs of French horns, which sometimes argue with the trombones (Riddle's own instrument) or yield to the double reeds, which provide a constant transparency to the soul's dark journey into the facelessness, moods, and existential postures of loneliness. From the nadir of an absolute silence the lost soul returns to the world of nature, in which it experiences restoration and a connectedness to its natural origins.

The attention to vocal-orchestral dynamics (especially in the age of microphones and volume equalizers) and to exquisite detail (rewarding the listener who chooses to focus only on the instruments) is perhaps unrivaled in popular music. Gil Evans (on Miles Davis, "Sketches of Spain") and Johnny Mandel (Shirley Horn, "Here's to Life") are examples of later arrangers who bear witness to the influence of Riddle's deftness and lightness of touch--even with the use of martial horns in a dampened chamber piece, but few arrangers in popular music sustain Riddle's versatility, variety and close shadowing of his story-teller.

The spray of "Ebb Tide" hits vocalist and listener with the force of a cleansing baptism about renewal rather than the romantic hero's stereotypical renunciation of life without the beloved. It's also the ironic lyric of the earlier "What's New," in which the soloist uses Riddle's trombone to insist that anything new is not wanted--only constancy, however "boring," can restore and heal. The song's lyric may be an argument for complacency, but as revisited and revisioned by Riddle and Sinatra it's a soul-stirring anthem to the creativity of American popular music in the hands of two of its foremost poets.

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Despite going to Stevens Tech in Hoboken, where Frank used to run around our track to build up his lungs, I've always struggled to appreciate his talent. Intellectually, I know it's there, but it's hard to separate the man from his music. At least it's possible, though, unlike with Bing Crosby who was not only a ghastly human being, but a hypocrite on top of it. At least with Sinatra, you knew what you were getting.

My all-time favorite singer of that type of popular song remains Fred Astaire. He lacked Sinatra's voice, but nobody put the lyrics across like Fred. He was also, apparently, a really nice guy and had a wonderful self-deprecating quality.

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Loved this column. Sinatra is so complicated in so many ways. He was able even to capture the hearts of many whom he abused. His problematic relationship with Australia notwithstanding, there is a radio station in Perth that still has a daily Sinatra hour radio show ... every day. While Frank remains my favorite singer ... well, after Ella Fitzgerald, I do regret what his career and influence did to the career of that other Hoboken singer, Jimmy Roselli, who deserved more and better.

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Sep 24, 2021Liked by Ted Gioia

Bobby Darin had the vanity and smugness you mention. And yet, many of the studio musicians who adored Sinatra resented Darin. Maybe it was his swagger laced with a juvenile streak. I'm with you on the 50's Capitol Sinatras. There are gems in the earlier Columbia recordings. I prefer "Why Try to Change Me Now" to his later Capitol remake. I wouldn't want to leave an article on singing without mentioning Mel Torme who was, though swaggerless, the best musician of them all. Was Bing Crosby to laid back for his own brand of swagger to be noticed? I see it plain. Watch him with Frank in "High Society" and you tell me. Different generation represented, though.

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Sep 24, 2021Liked by Ted Gioia

Great piece. I recall my parents' generation of men thinking that "My Way" was just terrific; to them, I think it was some kind of wistful "I hope I've left my mark on the world" message. It's my hope that, as time passes, what will thrive will be Sinatra's early and middle work -- the timeless arrangements, the incredible respect for lyrics, the phrasing, the intimacy, the introductory verses that many don't sing anymore (which Sinatra often used as extra bridges), and the more obscure songs he honored ("It's Sunday", "Everything Happens To Me", "Look At Me Now"). Many great artists' personas, personal lives, and less-than-great work have become more artifacts of their time than reasons to judge them, and I hope that turns out to be true for Sinatra as well.

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There once was a mediocre restaurant named "My Way" south of Saratoga Springs NY. It was filled with Sinatra memorabilia. Their "bread" came in a flower pot and the rest of the food was almost inedible.

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Excellent take on him as mirror of our culture during those years. I was never a huge fan. The only albums I own are with Count Basie "It Might As Well Be Swing" and a compilation from 1953-1060.

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Blame Paul Anka for the s*** lyrics. They are awful. Yes, Frank sang them, but it’s not all he did in his career. I attended a seminar once where Branford Marsalis said, ‘Sinatra was a great singer, but he was NOT a musician.’ An old famous record producer (whose name escapes me) was the other header at this thing. He agreed. I was horrified! I told Harold Mabern about this. He just said ‘WHAT????’

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Sep 23, 2021Liked by Ted Gioia

As bad as off-key karaoke is that line “If not himself, then he has not.” Unless it’s supposed to be “nought”?

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Have you ever attended a Sinatra concert, Ted? Curious…

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Sep 23, 2021Liked by Ted Gioia

That was the point of my biography of Sinatra 20-some years ago. Whatever else he did, he mirrored the culture, from cocky kid to blowhard, from FDR to Ronald Reagan.

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Sep 23, 2021Liked by Ted Gioia

Thanks for an interesting column. Personally, for all his gifts, I have never been able to get past the Sinatra persona. Maybe we just know too much about him. I thought the comparisons to Billie Holiday and Louis Armstrong here were particularly apt.

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