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Eight Sinatra Surprises
ByYes, of course I know, everyone knows this one. It’s his late-career big hit, the title song of the Scorsese movie, first performed by Liza Minnelli. So what could be surprising about this milestone Sinatra recording?
Yeah, it's possible. Listen to Ella scat on How High The Moon and you hear a genius singer who came from jazz territory and could riff like an instrumentalist. Frank really wasn't a jazz singer and had just one little joke scat, "dooby dooby doo," at the end of a song he hated (even though he turned it into a big hit). That genius singer came from a jazz-neighboring territory whose capital was Tin Pan Alley.
If Sinatra wasn't a jazz singer, did he still produce skillful improvisation, different reads of familiar songs, jazzy entertainment even for largely non-jazzy audiences? I'd say he absolutely succeeded on all those counts. When he cut a strong and eclectic LP with Count Basie's band and later a narrowly successful one with

Duke Ellington
piano1899 - 1974
The eight recordings below would commonly be listed under the bland category "traditional vocals" rather than "jazz." No matter. I think each of these Sinatra performances is in some way brilliant and surprising, though that's not a common category.
Some Enchanted Evening
This dreamy love song from Rodgers and Hammerstein's 1949 musical South Pacific was performed famously by Ezio Pinza, also by Frank Sinatra in 1949 and 1963... less famously by Harrison Ford in American Grafitti and by

Bob Dylan
guitar and vocalsb.1941
Andrew Lloyd Weber called Some Enchanted Evening ..."the greatest song ever written for a musical." A less enchanted listener might call it lovely but logy.
Why would Sinatra record this song one more time in 1967? He and premier arranger Nelson Riddle cooked up a surprising serving of a favorite recipe, turning a slow ballad into a finger-snapping swing song.
Band plays a big, brassy intro, then quiets for Frank, who enters in the song's conventional tempo: Some enchanted evening Band echoes the line, but loudly, in fanfare style Frank: You may see a stranger Band again echoes in loud fanfare At the stanza's last line, Sinatra happily gives in to the high-energy band and they take this South Pacific serenade off on a ride jumping with brass and percussion.
Through Frank's exuberant closing "Never, never, never, never . . . NEVERRRR . . . never let her go!" this curveball ballad is a passionate lark, having fun with the song's sentimentality.
Well, that's how I hear this track, but the few reviews I've read mostly pan it as wrong-headed and un-enchanting. Surprises tend to get mixed responses.
From This Moment On
This surprise is a subtle turn of arrangement to great effect. The song is by Cole Porter, originally for the 1950 musical Out of This World, but dropped in rehearsals. Three years later it was included in the musical Kiss Me, Kate, a modern adaptation of Shakespeare's The Taming of the Shrew.Here is the weird film version of Kiss Me Kate's staged "From This Moment On," which somehow manages to make Ann Miller not charming and dress the budding major choreographer Bob Fosse in a clown outfit.
So, outstanding a songwriter as Porter was, this song was deemed a flop in Broadway rehearsals and was a goofy dance number when included in a movie. Yet Sinatra and Riddle turned it into a thrilling, heavy-medium-beat swing song in his 1957 album, A Swingin' Affair (excellent in each of its 15 tracks).
A first-time listener to this track as it heats up might guess that the beat gradually accelerates. It doesn't. The quickening-pulse energy of this recording is created only through deft orchestration and the dynamic mood Sinatra and Riddle create. Surprise swing.
Forget To Remember8/18/69
There's an easy surprise in this Sinatra ballad: Hardly anyone has heard it. That would have included me, had I not bought the carefully-selected 1990 4-CD set The Reprise Collection. Jonathan Schwartz' liner notes call this recording a "lost work of art... never before released in the United States on anything but a 45." A 45?? Well, that's what the notes say.
This track was cut two years before his brief retirement. Listening to it, you hear Sinatra hasn't lost the voice. But as the '60s rocked on, he complained increasingly about the quality of contemporary songwriting. (If you were ever in an audience happily cheering when the orchestra struck up "Strangers In The Night," his hatred of his 1966 hit might surprise you as it once surprised me.)
The excellence of composition and performance in Forget To Remember was never widely circulated. The liner notes make a neat point about this orphan recording. Rather than calling it a saloon song like his two famous drown-your-sorrows classics, Forget... is described as ..."a haunting, rangy torch song."
I recommended this song to a very accomplished professional singer I happen to know. She told me the song was boring. OK, my surprise.
Long Ago and Far Away
This wistfully powerful performance is from the 1945 open-air concert honoring songwriter Jerome Kern at the Hollywood Bowl. The 29-year-old singer uses his signature microphone control and "parlando" lyrical whisper to create a dramatic masterpiece of this songin tribute to a great composer who was, as it turned out, in the last months of his life.The surprise here is mostly for people who only know Sinatra as the older, full-throated baritone of big Las Vegas rooms and New York, New York. His breakthrough in the early 1940s was actually based in his skillful understatement.
New York, New York
Yes, of course I know, everyone knows this one. It's his late-career big hit, the title song of the Scorsese movie, first performed by Liza Minnelli. So what could be surprising about this milestone Sinatra recording?The surprise is in its dramatic high point, sometimes called a hook. It's a single word, actually a single syllable that Sinatra slides downward in jazzy drama.
Could any other singer turn this word into such nifty drama? The word is "and." Just listen.
Come Fly With Me
One of the most popular and enduring Sinatra standards, Come Fly With Me is recognized by many from the opening bars with their ascending tremolo violins and muted trumpets.Listen to this Sinatra standard for the 10th timeeven more so by the 1,000th time, as I might haveand you'd assume there is no surprise to be found, not in the arrangement or the performance. But there's a big one. Just try to sing along with Sinatra's vocal.
A professional could do it with some study, but Sinatra's phrasing is so singular that an imitation would be tough. He's well-known to critics and musicologists for "lagging the beat," a style he adapted originally by studying

Billie Holiday
vocals1915 - 1959
The surprise on "Come Fly..." is how far he often trails the band, sometimes a whole beat or more. Just as surprising: how natural and rhythmic his extreme lag sounds. It's as if he has a swaggering message underlying the lyrics: "I'm Sinatra and I'll catch up to the band when I damn well please."
Monday Morning Quarterback
This late saloon song is little known, even to many Sinatra fans. Its obscurity might surprise anyone familiar with his earlier salooners "Quarter to Three" and "Angel Eyes." Maybe the football metaphor only works selectively. But at 65, Sinatra brings heartfelt wisdom to this account of a failed relationship, presented as an aging, much-injured ex-quarterback might.Ol' Man River
The great Kern-Hammerstein anthem from Showboat provides another of Sinatra's third-time's-the-charm recordings, and another big surprise, though one more soft-spoken than Some Enchanted Evening. Frank reaches for great craft reaches quietly and grasps it dramatically.This 1963 recording of the 1925 composition is less well-known than Sinatra's earlier performances. In 1944 he recorded a definitive version for Columbia, then two years later went on camera for the Kern biopic Till The Clouds Roll By, resplendent in formal whites in front of a large formal-whites orchestra and chorus, and perched on a weirdly sculpted white riser.
Sinatra's 1963 recording of a poor showboat stevedore's despair is also deep and moving. What could be surprising about this performance? The surprise happens near the song's end, as the bridge ends with "Ya get a little drunk and ya lands in jail," then moves to the concluding verse.
Sinatra's baritoneno longer the 1939 tenor but rarely visiting a note this lowdrops down on "jail" from D to G, then quietly descends further to E, as if darkly dramatizing the stevedore's hard times.
He doesn't stop there. Using a device perfected over the years, he emotionally connects two separated lines by moving to the verse without a breath, rising back with I gets weary...
Then, after 18 seconds of glorious (and breathless) performance, Sinatra takes one of the very few audible breaths in his long recording career. Hearing that breath from that singer might be even more surprising than the stunning low note.
Taken as a whole, his 1939-1997 career was an era-spanning wonder, often surprising.
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