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Frank Sinatra: My Way

Frank Sinatra was famous for “My Way”— the song and what it said about him. Music was personal for Sinatra. It was the one thing in his life—perhaps the only thing—that he felt absolutely certain about. Everything else—performing, acting, celebrityhood—was secondary. He could be cavalier about acting in movies and joking around with Dino and Sammy on a Las Vegas stage, but when it came to his music he was deadly serious. This was especially true when making records, a process Sinatra controlled every step of the way.

Here’s how it was done. First, Sinatra picked all the songs. Oh, he might allude to a record company exec wanting this song or that, or the producer putting together a playlist, or the arranger having picked some of the material. Absolutely not true. Sinatra might accept a suggestion or two, but the final decision was his alone. Sinatra would pick the songs, meet with the arranger to determine the right key for each song, and whether or not the song should be arranged as a ballad or a swinger, for jazz band or string orchestra, or both. Sinatra was very particular about all of this. He knew exactly what he wanted, and chose arrangers who could carry out his vision.

Once the songs were selected and Sinatra and the arranger had gone over the material, Sinatra would then meet with his pianist, Bill Miller, and always at the singer’s house. Sinatra could not read a lick of music or play an instrument, so he relied on Miller to help him become familiar with each song. While Miller played, Sinatra would sing each song over and over again, searching for the inner meaning of the lyrics, to discover which words to emphasize, and which not to, where to pause, and for how long, where to be soft, and where to be strong, until he reached the point where he had the exact right inflection for each phrase. Some songs came easier than others, but the process always consumed long hours and several days. The result was utter mastery of the material. Sinatra didn’t write songs, but at the end of his sessions with Miller he knew them intimately, as if he had written them himself. He sang with such understanding and conviction that it seemed he was singing his life story. In fact, having chosen the songs, that is exactly what he was doing. Sinatra relied on many people to make records, but the key to his art was in personally selecting the songs, and rehearsing them to perfection.

The recording sessions began promptly at 7:00 in the evening. When Sinatra arrived—usually at seven sharp—he expected the studio orchestra to have warmed up and be ready to go. This put a great deal of strain on the arranger, who had to write the score for 10 to 14 songs, often on short notice, and to have them ready by the start of the session. It was never easy. Nelson Riddle sometimes worked all night before the first session, while Billy May was famous for finishing scores and handing them to the copyist while the band was tuning up. The idea was to be ready WHEN the singer arrived. Riddle and May always made the deadline—if barely. Those who needed more time to compose, such as Quincy Jones, employed “ghost” arrangers to meet the deadline.

If Sinatra was in good voice, and the orchestra was cooking, the song was recorded in one or two takes. If something wasn't quite right—Sinatra had incredibly good hearing and detected things others missed—then another one or two takes was required. Sinatra reveled in the moment when the orchestra took flight and the instrumental soloist would stretch for the high, hard notes. Mistakes would be made at such moments, and afterwards the producer would emerge from the booth shaking his head, saying, “Frank, we need another take.” If Sinatra was moved by the performance, he would wave him off. “No way to top that. Next tune.”

Recording an album generally took three sessions, with each session lasting about three hours. The songs were cut “live”—singer and orchestra recored at the same time. Overdubs were rare. The analogue tapes would then be mixed down, mastered, and sent to the record plant for pressing. The album would usually appear in record stores about a month later.

Below are reviews of three Sinatra albums that are among his very best:

SONGS FOR SWINGIN’ LOVERS (1956) — In 1953, Frank Sinatra’s career was over. He’d been fired by Columbia Records and publicly disgraced by his breakup with actress Ava Gardner. At the same time, a song arranger was beginning to make a name for himself in Hollywood. The arranger was Nelson Riddle, who was doing the charts for the singer who had replaced Sinatra as the nation’s favorite balladeer—Nat Cole. After Sinatra’s agent failed to get the singer signed with RCA in New York, a then-small West Coast jazz label expressed interest. One thing led to another and, now with Capitol Records—and partnered with Nelson Riddle—Sinatra’s recording career shot off into the stratosphere bigger than ever. Riddle’s arrangements were the catalyst: imaginative, lightly textured and lively, even for ballads, allowing Sinatra to change from the boy singer of the 1940s to the urbane swinger of the ‘50s and ‘60s. The album that personified the changed was “Songs for Swingin’ Lovers.” Fourteen irresistible uptempo toe-tappers that had the jazz critics raving, the public buying again, and the kids swinging at sock-hops from coast to coast.

The song that best personified the change was Cole Porter’s “I’ve Got You Under My Skin.” It was the tune that was almost overlooked. At the last moment, Capitol execs decided they needed another song to fill out the album. Sinatra choose “Skin” and Riddle was asked to come up with an arrangement by the following day. “It was a work of pressure,” recalled Riddle, “because I had to stay up quite late and finish it.” In fact, Riddle finished it in the car on the way to the studio. Sinatra had specific instructions. He wanted a long crescendo for the bridge (the instrumental break between verses). Riddle thought of Ravel’s “Bolero,” which had “the most calculating orchestral crescendo” that builds agonizingly slow to a musical peak. Riddle liked the idea but was stuck on how to bring it off in a three-minute pop tune. He was thinking of Afro-Cuban rhythmical patterns when he remembered a record by Stan Kenton with decided Afro-Cuban rhythms, called “23 Degrees North, 82 Degrees West” (the geographical location of Cuba).

“I remembered that trombone back-and-forth thing (that Kenton employed),” said Riddle. “I was always fascinated by it.” There was only one trombonist on the West Coast who could do Riddle’s chart justice—jazz trombonist Milton Bernhardt. He was called shorty before the session was to begin. Could you be here in 20 minutes? Bernhardt rushed to the studio and later recalled that both Sinatra and Riddle seemed to know that this would be a very special track and they were keen to keep doing take after take until they had it exactly right. How many takes? For Sinatra, who didn’t have a lot of patience, two or three, four at most. Not this time. Not with this tune. Sinatra was not satisfied until the 22nd take. Bernhardt, who had to hit the same lofty notes over and over again, was exhausted when Sinatra said at last, "Next tune."

ALL ALONE (1962) — A sleeper in the Sinatra canon. Old fashioned songs, written mostly in the 1920s, in waltz time, many by legendary composer, Irving Berlin; arranged by the stoic string master Gordon Jenkins, and sung with tenderness and heart by Frank Sinatra. Sentimental songs, rendered smart and urbane by Sinatra, not smarmy or routine. The closing number, "Come Waltz With Me," written specifically for this album by Sinatra’s pals Sammy Cahn and Jimmy Van Heusen, provides the perfect finale for a perfect album. Familiar songs too, recorded by a host of singers over the years, but never better and never fresher than on this 1962 release.

The theme is loneliness, which is reflected in the opening number, "All Alone," and felt throughout. Under any other guise, this would be considered another Sinatra "saloon album" but somehow it's not. It's more than that. There's grandeur here, an elevated purpose at work, that somehow transcends categorization. These songs have a timeless quality about them. Most of them date back to Sinatra's youth and therefore have a special meaning to him, which comes across strikingly in his knowing and nuanced singing. These are sad songs with a sweet gentleness about them that Sinatra conveys with tenderness, and understated passion. "Charmaine," "What'll I Do?" "When I Lost You," “Oh, How I Miss You Tonight," "Indiscreet," all of which Sinatra makes his own. This is an especially classy album that a great deal of thought and care went into. Never a big seller, not until the CD era did the album get the recognition it deserves.

TRILOGY (1979) —"The most ambitious project of Sinatra's career," says jazz critic Will Friedwald. "It captures all of his sides: swinging, loving, serious, and grandiose.” Here's how the album was conceived. Sinatra was musically out of answers in the mid-1970s, having come out of retirement, and having tried his hand at being contemporary with two albums that were, alas, underwhelming. He was thinking of doing a country album, then thought better of it. Then of doing an album with Nelson Riddle comprised of songs with women's names as titles. A few tunes were recorded—"Emily," “Sweet Lorraine,” “Nancy,"—before the project was dropped. Then Sinatra read a column in the New York Times. In so many words, the columnist said: “Frank, forget about being contemporary, do what YOU want to do: pick the songs YOU want to sing, work with the musicians YOU like, and by all means get back into the recording studio and do what you were born to do--make records.”

The result was “Trilogy," a three-record set, each record with a title: (1) “The Past," a collection of Tin Pan Alley classics, many never previously recorded by Sinatra, and arranged by swingin' Billy May; (2) “The Present," a sampling of contemporary tunes arranged by “the Puccini of pop,” Don Costa, including what was to become another of Sinatra's signature songs, “Theme From New York, New York"; and (3) “The Future," a song suite written and arranged by Gordon Jenkins, about space travel and the end of war, that was, alas, stillborn, despite Sinatra's valiant effort to give it life.

The best of the three records—and vintage Sinatra—is the “The Past." “The Present” is good but let down by a few songs that do not exactly fit the Sinatra persona. The strongest cuts are the aforementioned “Theme From New York, New York,” and George Harrison’s masterpiece, “Something.” “Something” is particularly noteworthy because it was arranged for string orchestra six years earlier by Nelson Riddle. Indeed, one can't help but feel that had Riddle been a part of the project, the Sinatra-Riddle relationship would have rekindled the old magic and “The Present” would have been equally as sensational as “The Past." Word has it that Riddle wanted to be involved but—incredibly—no one asked him. The less said of “The Future" the better. The good news is Gordon Jenkins made amends two years later with "She Shot Me Down,” the last great Sinatra album.

Final note: Sinatra seldom listened to his own albums. Why? For one, he preferred classical music, especially string quartets. But also because he gave each album his all; he milked every last ounce of emotion out of each song and so the mystery was gone. No need for him to hear the playback. Next tune.

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