Frank Sinatra had a long career, one that spanned several musical eras. Today’s music fan can pick and choose from among them, from his early days as Tommy Dorsey’s “boy singer” to his triumphant “New York, New York” period in the early 1980’s. As a kid who grew up in the 1960’s, the Sinatra of my youth was the aging balladeer who was trying to navigate the post-Beatles world of popular music. 

AM radio was still a thing – neither of my parents had a car that picked up the FM band until the early 1970’s – and the big AM station of my childhood was a middle-of-the-road powerhouse called WOWO. Frank Sinatra was a regular on their playlists, with songs like “It Was A Very Good Year” (1965), “That’s Life” and “Strangers In The Night” (1966) and his 1967 duet with his daughter, “Somthin’ Stupid”. 

In my adolescence I became tuned into jazz. I had never thought of Sinatra as a jazz singer. He had been a crooner as a young star, and in his maturity he seemed to revert to his roots as a balladeer, though one with a thickened and huskier voice. I thought of Francis Albert Sinatra in much the same way as I thought of Elvis Presley – a pop music phenomenon in youth who transitioned into a nightclub performer for older listeners. Sinatra’s string of classic albums from the 1950’s (with his often-collaborator Nelson Riddle) might have modified my view, but my sole exposure to 50’s Sinatra had been a single album of ballads that had been in my mother’s music collection (“Where Are You” from 1958). That exposure had buttressed my view that Sinatra had always been a popular balladeer and little more. 

I was in college when a friend’s brother became a big Sinatra fan. Based on my experience, I didn’t really understand that and could not see his enthusiasm as anything other than a way to become counter-cultural after the first kind of counter-cultural had become mainstream. What changed my mind? Listening to the album “Ring A Ding Ding”. 

Released in 1961, this is an album that is often overlooked. The 50’s albums with Nelson Riddle on the Capitol label usually soak up the spotlight for those who love “Rat Pack Sinatra”. And for good reason, as there is a lot of great music there. But Sinatra had chafed as his contract with Capitol was concluding, and his final albums for that label seemed “phoned in” as he was making preparations to launch is own label – Reprise Records. This album was the very first Reprise release – for Sinatra or for anyone else.

Sinatra initially had wanted Nelson Riddle to do the arrangements and direct the orchestra, but Riddle was tied up with projects (and a contract) for Capitol. There was he same problem with his other favorite collaborator on up-tempo projects, Billy May. It was then that Frank reached out to a young jazz guy named Johnny Mandel. Mandel was in his mid 30’s (and about a decade younger than Sinatra), and had played both trumpet and trombone in some name bands of the late 1940s and early 1950’s, including a 1953-54 stint with Count Basie. Mandel had also attended some music schools and was a skilled writer/arranger, which landed him in Hollywood to do film work in the late 1950’s. He is probably best known today for having written the theme for the movie (and television show) M*A*S*H.

In a 2008 interview, Mandel recalled that he had come to Sinatra’s attention through some arrangements he had done for singer Vic Damone for a show in Las Vegas. Sinatra summoned Mandel to a meeting and things went from there. The album concept was for a jazzy, up-tempo vibe, and Mandel was encouraged to do is own thing rather than try to emulate what Riddle or May might have done.  I had never known until researching this piece that Mandel got pressed for time and had to subcontract a few of the arrangements, and that he was not wowed by the results. But then name a creative type who thinks someone else can do his project better than he can.

Picking samples from this album would have been hard – everyone knows great albums that have “that one song” or “that one track” that we could have done without. Ring A Ding Ding is not one of them, and every single track is well above average. Johnny Mandel himself came to my rescue and named his favorite three arrangements on the album, so that’s settled.

“Ring A Ding Ding” (the album) followed a familiar pattern of a new title song, followed by new treatments of standards. ”Ring A Ding Ding” (the song) was the album lead-off, written by Sammy Cahn and Jimmy Van Heusen – a team who had penned several Sinatra hits. This song sets the mood for the entire album, and shows Frank Sinatra at peak swagger. He was undoubtedly excited to be the literal chairman of the board for the new record label, and this arrangement (and others like it) punched harder than anything he had done. Musically, I mean. 

Frank Sinatra started his career in front of the top big swing bands of the big band era, so the ability to feel that style of music went deeply into his bones. Mandel’s arrangements and this band’s performance showed that when a band could punch fast and hard, Sinatra was every bit up to the task. Or perhaps it was Sinatra at the peak of his ability to punch fast and hard that brought the band along with him. I will not pick a side here, but will go with this being a great synergy.

Next up is “In The Still Of The Night”. Some of Sinatra’s best work was done with Cole Porter songs, and this one is no exceptions. But this time, Mandel turned the song from a mellow crooner’s delight into a hot treatment that works despite the way the lyrics might suggest a more tender approach. 

As with many things by Cole Porter, it is a fairly complex song that offers plenty of places for both singer and band to shine. For those who came of age after the age of the LP record album, the order of songs could be almost as important as the song choices themselves. This track finishes out Side 1, and was a strong finish that urged the listener to flip the disc to Side 2 for more good stuff. This track accomplished that role, and then some.

In the same way, the opening song of Side 2 had to help the listener overcome the inertia of a comfortable chair and (maybe) a martini – this was the job of “The Coffee Song”. This was an old chestnut that Sinatra had been the first to record after it was written in 1946. Sinatra was then at his peak of popularity as a solo artist, but he was still a young crooner who excelled at a more relaxed pace. The 1961 version of the song is so, so much better. 

The song itself was probably written as a throw-away in an era when pop songs were churned out with great rapidity, and Frank’s early version was fun, but not one of his more memorable hits. This time was different, and I count this as one of Sinatra’s very best up-tempo recordings of the era. Listening to Sinatra interact with a really good band is always a delight, and they do not disappoint here. As an example, listen to the line “You-can’t-get-cherry-soda-cause-they’ve-got-to-fill-that-quota” and you can detect the way the singer is just a fraction of a beat ahead of the band, as if to pull them along, while at other places (like the following line) he is smack dab on the beat. I could listen to this record a hundred times in a row before I would tire of it.

Frank Sinatra’s career seemed to follow two conflicting arcs. First was that of his amazing voice, an arc that began with almost vocal perfection in his youth, and which slowly lost its range and elasticity as the performer aged. The second was in his style, which started low as a garden-variety band crooner and which built over the decades in ways that made the man wholly unique in his abilities to craft a song into his own.  

The album “Ring A Ding Ding” may have been where those two arcs crossed. This was not the young singer whose lovely voice floated above a hard-swinging band or the older singer who used style and personality to overcome a voice that had lost much of what had made it special. All of life is a compromise, but this record is a compromise between voice and style that is worth a listen. It also proved to me my gateway drug for an appreciation of Frank Sinatra and the entirety of his amazing career.

Note – there is a good 2008 Interview with Johnny Mandel, found at https://www.jazzwax.com/2008/10/interview-joh-5.html