It’s 1953 and Frank Sinatra is at the bottom. Like…the bottom. The public doesn’t like that he left his wife and kids to be with Ava Gardner. Mitch Miller at Columbia figures Frank is done so it’s time to sing with dogs. On stage – playing to a half-empty house – Frank’s voice gives out: “dust” comes out, he says later. A new batch of singers is eclipsing his popularity: Johnny Ray, Frankie Laine, Perry Como. Frank marries Ava but they battle constantly and this takes a toll on his health. And yet… There’s buzz around Hollywood that Sinatra’s work in the in-production “From Here to Eternity” is stellar. And there are a couple of very astute men working for Capitol Records who feel Frank still has it and they plan to bring him on board and pair him with a young arranger named Nelson Riddle. When they do, the rest, as they say…

Long story short: Sinatra wins the Oscar for “From Here to Eternity”. Then, he records “I’ve Got the World on a String” with a vibrant chart from Nelson and effectively declares his return. Not only with a vocal full of character and life but with an attitude and a declaration of intent. The very title of this number states his creed. Here, in Part Three of this series, Sinatra’s work starting with joining Capitol in 1953 and ending at a proposed pivot point in the spring of 1966 is explored. It is an era of supreme dominance in all areas of celebrity by Sinatra. Here, of course, we are focusing on his recordings and the way in which they repainted the landscape of popular song craft. This story will be told by looking at seminal recordings from this era and also at the albums he recorded that became hallmarks of genius and definitive representations of the pinnacles of artistry.

Sinatra arriving at Capitol coincided with the Long Playing 33 1/3 RPM album becoming the standard of the industry. Sinatra embraced this format immediately putting out his first long-player at Capitol. Ever wonder why “Strangers in the Night” is usually the only song of Sinatra’s people can name? Because there are few other single songs they are aware of. He was NOT a ‘singles artist’. Sure, he had chart hits but he didn’t burn up the singles charts. He never had a gold record (million dollars in sales) until 1966 (“Strangers”). He used to joke with Princess Grace that she had a gold record (“True Love” with Bing Crosby) before he did. And that perfectly illustrates my point – it was about the package, the album, the ‘tale’. He was an auteur, a storyteller and it took him longer than 3 minutes to tell his story whether it was one of jubilation or one of suicidal despair. However, you can point to sublime moments found on these albums as prime examples of a singer’s art. Briefly, a word on the albums themselves. If you really want the skinny on the Chairman of the Board, go out and buy “In the Wee Small Hours” (1955) and “Songs for Swingin’ Lovers!” (1956). With the former, you get a torch album that is perfect. It has a mood and a tone coupled with Nelson Riddle’s subtle orchestrations and topped off by Frank at perhaps his best. His voice is expressive and desolate without being sappy. On the latter, you get another Sinatra/Riddle combination that is perfect. This time, the jams get kicked out. Never has a singer been presented in a more ideal setting. “To swing” is defined for a new age. This is the album that all traditional vocal albums after it have aspired to. A similar twosome was presented in 1958 with the releases of “Come Fly With Me” and “Frank Sinatra Sings for Only the Lonely”. “Come Fly” has maybe the greatest album cover of the era and it is rare for Frank in that it mixes ballads with uptempo numbers. “Lonely” is a torch album, yes. But here the landscape has been absolutely leveled. Where “Wee Small” presents resigned depression, “Lonely” showcases open-wound suicidal despair. To wrap up great albums from this era, Frank’s second outing with Count Basie – “It Might As Well Be Swing” – is the aural representation of a strutting, suit-wearing, hat-tilting, finger-snapping, life-living time. “The Capitol Collectors Series” offers a great sampler of some better-known singles from this era. It’s actually the first FS CD I ever bought. Here are your Top 20 Sinatra recordings from 1953 to 1966: the “swinger” era.

20. “Falling in Love With Love” (1961 – from “Sinatra Swings”/”Swing Along With Me”) — Someone says to you “explain Sinatra to me”. Tracks like this are a great start. Nothing spectacular just 1 minute and 49 seconds of breezy, fluid, languid, cool, confident singing. The best example? No, but a fine starting point.

19. “I’ve Got the World on a String” (1953 – single) — The song that reintroduced Frank to the world. Not the first song he recorded upon arriving at Capitol but the first one that declared his intent. Confident singing, brash lyrics. The first song that gave us the Frank we know from the ’50’s and ’60’s.

18. “Mood Indigo” (1955 – from “In the Wee Small Hours”) — This Ellington song is second on the album after the title track. Just a wonderful performance that helps set you up emotionally for the long journey into night to come.

17. “You Make Me Feel So Young” (1956 – from “Songs for Swingin’ Lovers!”) — Like #20, this track is just textbook Sinatra. This particular recording is celebrated all the more because it is the perfect kick-off for the greatest album ever made in this idiom.

16. “Nice ‘n’ Easy” (1960 – from “Nice ‘n’ Easy”) — One of the better singles from the Capitol years, this one’s title says it all. Frank is chill and this one stands out partly because you can hear him snapping his fingers. A rare case of a single being used as a title track for an album. Unfortunately in this case, the rest of the songs on the album are slow ballads – as opposed to the cool/breezy title track – from the Columbia era.

15. “(Love Is) The Tender Trap” (1955 – single) — From the film of the same name, this one benefits from it’s association with that excellent movie featuring Debbie Reynolds and Celeste Holm. Great lyrics and another great swinger. FS revisited it years later on his first album with Count Basie.

14. “Come Rain or Come Shine” (1962 – from “Sinatra and Strings”) — A moody, elegant and powerful reading of a dramatic song. Showcases Sinatra’s ability to emote and “act out” a lyric.

13. “The Song is You” (1959 – from “Come Dance With Me!”) — “I alone have heard this lovely strain…” Such a wonderfully sung line from one of the most satisfying uptempo numbers of Frank’s career. A straight-up swinger from an album that won three Grammys and stayed on the charts for 140 weeks!

12. “Hello, Dolly!” (1964 – from “It Might As Well Be Swing”) — Talk about a swinger. This track is almost heavy metal. With shout-outs to Louis Armstrong, Frank and “Splank” (Basie – check the cover) and Co. absolutely blast their way through this. It is as energetic and hard-driving as anything FS did. Smokin’!

11. “This Was My Love” (1960 – b side of “Nice ‘n’ Easy” single) — The “No One Cares” album was an early Frank purchase for me. I was really thrown by the fact it was all ballads. Once I got over that, “This Was My Love” – included as a bonus track – really bowled me over. Such quiet, tender singing from The Swinger and such a sumptuous orchestration. Gorgeous. “Others may cherish fortune or fame. I will forever cherish her name”.

 

10. “Ring a-Ding-Ding” (1961 – from “Ring-a-Ding-Ding”) — One of a handful of tracks that can be used to perfectly describe Sinatra and his world at this time. The boys had their own language and this phrase meant “let’s go, let’s get it on, let’s party!”. Frank had his songwriter’s come up with a lyric and he swung through it on this his first album release for his newly created label, Reprise Records.

9. “All the Way” (1957 – single from the film “The Joker is Wild”) — One of the more popular singles for the Chairman. Introduced by Frank in the movie in which he portrayed comedian Joe E. Lewis, this tune won the Oscar that year for Best Original Song. A wonderful string-laden chart and strong singing. This one is very “Sinatra” and has been covered dozens of times.

8. “Come Fly With Me” (1958 – from “Come Fly With Me”) — Similar to “Ring-a-Ding-Ding”, this is a textbook swinger and theme for Sinatra. It’s also very of it’s time, being from the era of continental jet-setting. The lyrics urge the young lady to board the plane and throw caution to the wind. This one is also very “Sinatra” in attitude. In a later recording for Reprise, he sneaks in “and don’t tell your mama” at the end.

7. “It Was a Very Good Year” (1965 – from “September of My Years”) — Another song that is readily identified with Frank. In 1965, he turned 50 and marked the occasion with this album of songs sung from the perspective of a middle aged man looking back. In many ways, the album was an end point of sorts and ushered in a more mature sound as Sinatra led his legion of fans into the ‘September of their years’. The song itself features another stunning chart from Gordon Jenkins. Originally a folk song, Jenkins loaded this version with lush strings that state a phrase that grows in resonance as the song goes on. The lyrics are poignant and this song is a unique triumph in Sinatra’s oeuvre.

6. “Ol’ Man River” (1963 – from “The Concert Sinatra”) — I’m actually coming to this song late in my life and my journey through Frank’s music. “The Concert Sinatra” was an ambitious undertaking from Frank and Nelson Riddle. Frank had always been interested in longer song forms and this was his chance to embrace his highbrow aspirations and record eight songs with a larger-than-normal orchestra. The timeless “Ol’ Man River” is just one example of the many high points on this record (“Lost in the Stars”). A showpiece of mammoth proportions, Sinatra cements his reputation as a serious and gifted vocalist with his performance here. The dark wood quality of his voice was never brought to the fore in a more spellbinding setting than this. Truly remarkable. Headphones suggested.

5. “One for My Baby (and One More for the Road)” (1958 – from “Frank Sinatra Sings for Only the Lonely”) — Those who know, know. This is the track. The performance that displays what makes Sinatra Sinatra more than any other. He’d tell you himself; at heart, he was a saloon singer. He sang in the dead of night, after the joint had closed. And this was the song. When he sang this live, it was showtime. He was lit by a single spot, lit a cigarette and sang while just his pianist, Bill Miller, played. This is Sinatra. “It’s quarter to three. There’s no one in the place except you and me…” (This song was recently featured in the film “Blade Runner 2049”)

4. “Fly Me to the Moon” (1964 – from “It Might as Well Be Swing”) — Meanwhile, in outer space… On a lighter note, here we are again at yet another lesson in swing from Francis and Bill Basie. Finger-snapping, grinning, head-bobbing perfection. In 1964, Frank’s version was played on the Apollo 10 mission that orbited the Moon. Five years later, it became the first music heard on the Moon when Buzz Aldrin took a portable cassette player with him when he stepped onto the Moon. Outta sight.

3. “In the Wee Small Hours of the Morning” (1955 – from “In the Wee Small Hours”) — In my opinion, his finest torch song. It’s the lyric: “In the wee small hours of the morning, when the whole, wide world is fast asleep, you lie awake and think about the girl…”. It’s the gentle Nelson Riddle arrangement: not grandiose or dramatic but quiet. An orchestra but a small orchestra. It’s the album cover: Frank, alone on a street corner in the middle of the night, no one around. For me, this is the perfect track to set up the perfect album of songs of lost love. Indeed, it sets up a long career of singing for the lonely in the wee smalls.

2. “The Way You Look Tonight” (1964 – from “Days of Wine and Roses, Moon River and Other Academy Award Winners”) — Kind of out of the blue, on an album with a ridiculously long name, Frank puts on a clinic. He ‘plays’ his voice like an instrument here. It’s an amazing vocal. And you know what? Nelson Riddle… Listen how he starts things off with tooting saxophones and those gorgeous muted trumpets. Frank here sings effortlessly. The man is 49 years old and yet he sings it breezy, light and youthful – and those reeds tooting all the while behind him. Not enough is said about this wonderful recording, this wonderful melding of Frank and Nelson, voice and orchestra.

1. “I’ve Got You Under My Skin” (1956 – from “Songs for Swingin’ Lovers!”) — Commonly referred to as Frank’s shining moment, the absolute pinnacle of his craft. His appeal, everything that we love about Frank is embodied in this recording. FS chose the songs and arranger Nelson Riddle for this album of uptempo numbers. A great many legends surround Frank’s recording of this song. He was a busy man and moved fast. This often put pressure on his arrangers to have charts ready when it came time to record. One legend claims that, called into action suddenly one night during recording of the “Swingin’ Lovers” album, Nelson finished up this arrangement in the back seat of a car as he was being driven to the recording studio. Another one states that after the band had learned the chart and ran through it the first time, the musicians gave Riddle a standing ovation. What is undoubtedly true is that the arrangement is commonly held as the zenith of the collaboration between Frank and Nelson. The chart features a general building – a crescendo – in terms boldly stated by the horn section. And then there is trombonist Milt Bernhart. His four-bar solo riding the crest of the climax of this crescendo has been singled out as a definitive moment in Frank’s recording career. It is exceedingly energetic and has been described as “startlingly out-of-control”. It “has become one of the most widely heard trombone statements in history…(it was) something hysterical, something historical”. All things considered, the recording is the preeminent example of high art in this idiom. Scholar Will Friedwald has gone so far as to suggest that Bobby Darin based the entire ‘lounge singer’ portion of his career on this one recording.

Up Next: The Long Journey Into Evening…