“To do is to be – John Stuart Mill

To be is to do – Jean-Paul Sartre

Do be do be do – Frank Sinatra”

                                    --Graffiti, Cambridge University Library, 1966

It was in the Mad Men era, before things got really weird, excessive and decadent.

People dressed up for airline travel. Mini-skirts were all the rage while gentlemen still adorned stingy-brimmed fedoras. Batman, Star Trek and How the Grinch Stole Christmas all made their television debuts in living color but Vietnam was beamed into living rooms nightly in black and white. The U.S. Supreme Court affirmed “Miranda Rights’’ and LSD was made illegal. Project Gemini was exploring new frontiers in outer space and, for the first time in 400 years, the leaders of the Catholic and Anglican churches exchanged fraternal greetings, on earth, in Rome.

As a counter to Berkeley’s counter-culture, Ronald Reagan was elected governor of California. The average home cost $14,200 and a gallon of gas cost just 32 cents. Mercury Record Company introduced the music cassette to the U.S. market and fans burned vinyl records in reaction to reading that John Lennon said the Beatles were “more popular than Jesus.” The Jimi Hendrix Experience recorded “Hey Joe.” And a 50-year-old, with a style and swagger all his own, won the Grammy Award for Best Vocal Performance, Male, for “It Was a Very Good Year.” The man was Frank Sinatra and the year was 1966.

This was the environment Sinatra was operating in 50 years ago. He was enjoying success again in the mid-sixties -- in music and movies, having returned from the brink of extinction in the early 1950s. But 1966 was different. There was a definitive creative tension in popular music that year, where the contemporary electric sounds --the cacophony -- were colliding with the more traditional acoustic sounds -- the symphony. In his astute cultural observation, author Jon Savage in 1966: The Year the Decade Exploded concludes, the year began in “pop” and ended in “rock.”

“It was the year,” Savage writes, “in which the ever lasting and transient pop moment would burst forth in its most articulate, instinctive and radical way.” The 7-inch single outsold the long-player for the last time. “After 1966, nothing in pop would ever be the same.”

The pace of change and the drive for even greater expression in popular culture, in general -- and music, in particular -- could render someone hopelessly dated and irrelevant rather quickly, if they did not act. Fear of being left behind competed with a desire to be current. Sinatra, too, must have sensed something in the air, that tension.

The year before, in 1965, Sinatra’s music (especially on the album September of My Years, which, incidentally, won Album of the Year at the 1966 Grammy Awards, and on “It Was a Very Good Year,” the single that yielded Sinatra the above Grammy for Best Vocal Performance, Male) was tinged with reflection and tortured with resignation, surely as a consequence of hitting middle age.

His first release of 1966 was in March, with Moonlight Sinatra. Recorded in late 1965, it was familiar territory, romantic and ruminative; another in a series of concept albums, playing off of Beethoven’s “Moonlight Sonata” theme. It was new but not innovative.

In his famous April 1966 Esquire magazine essay, “Frank Sinatra Has a Cold,” written mostly in 1965, Gay Talese noted that the entertainer “survives as a national phenomenon, one of the few prewar products to withstand the test of time.” But he still craved relevance, not just survival.

In 1966, Sinatra -- beyond The Voice but not yet The Chairman of the Board -- wanted to be cutting-edge, yet retain his classic style. Personally and professionally he reflected perfectly the “tumult” and “urgency” of the year Savage wrote about: Sharp-edged and sharply dressed, he held the freakish, Technicolor of bohemian hippiedom in absolute disdain. But he married Mia Farrow, then sporting a modern Twiggy-like hairdo, just 21 years old. And musically, as then-young music producer, Jimmy Bowen, said, “he wanted Top 40 radio… he wanted hits.” Where The Beatles were happening. As he had done over a decade beforehand, he would have to radically retool his sound. That would require adding a new instrument to the repertoire to introduce new tones and colors. Something hip.

The Vox Continental organ (and later the Hammond B3) was a staple in many of the mid-sixties hits in popular music. Transistor-based, it was able to replicate a “reedy, eerie” sound, but also looked and sounded futuristic. It was the signature sound on the Animals’ “House of the Rising Sun,” and used by the likes of The Beatles, The Dave Clark Five, The Monkees, and, later, The Doors -- all hit makers.

Recorded on April 11, 1966 and distributed hastily via plane and courier (fearing a version by Jack Jones would hit the airwaves before his version), Sinatra’s “Strangers in the Night,” (a product of producer Bowen and engineer Ernie Freeman) became a massive success, reaching number one in the United Kingdom (June 4) and the United States (July 2). It would be the last Sinatra song to hit the top of the Billboard charts and features a “surprisingly quixotic scat” coda: “dooby-dooby-do.” A new, but immortal, Sinatraism.

Despite the achievement, as Will Friedwald notes in his extraordinary book, Sinatra! The Song is You, “the rest of the Strangers [In the Night] album had been originally earmarked for another project; Sinatra and Reprise annexed the material under the ‘Strangers’ banner out of a quick need for an album to complement his mega-hit single.”

Ironically, the singer initially hated “Strangers.” Even with a melodic hook and moody hesitancy the sound came from familiar territory. The remaining collection, wrote Friedwald, was a “set so beautifully done it almost seemed as if Sinatra were apologizing for the original track.” And that’s where things got interesting.

Paired with long-time arranger Nelson Riddle (largely responsible for creating the classic Sinatra soundtrack, as defined by the test of time), it was Riddle who, according to an iTunes review of the album, “wanted to modernize Sinatra within believable limits.” Irrepressibly, “The Popular Sinatra,” announced the back cover to the LP, “Sings for Moderns.” In a kind of throw down, Stan Cornyn’s liner notes warn that Sinatra, “defies fad. He Stayeth.”

Two tracks, sequenced behind “Strangers,” heralded the new Sinatra sound, the organ-infused “Summer Wind” and “All or Nothing at All.” They were among “the last fully realized, top-drawer examples of the Sinatra-Riddle collaboration.”

The “Summer Wind” was the “greatest triumph” of the collaboration in its ‘60s phase, concludes Friedwald. The song employs two orchestras – the organ and the big band – that “become a countermelody and background riff to Sinatra’s exposition of the central melody.” Riddle constructed a stunningly catchy “leitmotif to represent the breeze,” where the organ lifts into a crescendo and softly fades away, the protagonist’s “fickle friend.” If anything, the organ adds a contemporary texture to the track. It reached number 25 in the charts on Oct.  1, 1966, but retains a remarkable staying power, a favorite of fans even today.

“All or Nothing at All,” a Sinatra ballad first recorded in 1939, was given a complete reworking; an up-tempo, jazz-inspired swinging swirl, the organ is even more emphatic. Riddle’s liberal use of it, combined with a more pop-oriented rhythm section, presents a modern, sophisticated masterpiece -- where the singer is at his most commanding, confident and in control, in years. Here, the organ and orchestra “don’t play at the same time but trade phrases back and forth like two warring big bands in a Savoy Ballroom battle.” It is arguably the quintessential post-modern Sinatra tune. So utterly cool, it never approaches parody status, a dreadful hallmark of some of Sinatra’s later work.

Released on May 30, Strangers in the Night would remain on the charts for 43 weeks and would be Sinatra’s last number one album, and, incredibly, his last with Riddle and his orchestra. Clocking in at 27 minutes and 10 seconds, a complex compression of old and new, the album would revitalize him. Indeed, Sinatra was back, standing tall, a hit maker again.

Keeping the momentum going, in July Sinatra at the Sands was released as a double album, featuring live performances of the 1966 incarnation of the brash,  Rat Pack leader. Taken from a series of shows recorded at the hotel’s Copa Room, in January and February of that year, it contains none of the year’s new material. Remarkably, it does not even anticipate the new sound or direction. Playful and cascading with attitude as wide as America, it does, however, showcase Quincy Jones’ fine traditional arrangements and Count Basie’s solid orchestra.

That’s Life, released on November 18, did further the exercise in experimentation, reaching number 6 on the album charts. The single, “That’s Life”, is propelled, right from the opening bars, by a rhythmic and melodic organ, more rooted in the blues, than jazz, and way up in the final mix. Gritty and a bit more raucous than its predecessors, the song peaked at number 4 on the charts, fittingly, on Dec,  24. After “Strangers,” it would be the second in a trilogy (the third being 1969’s “My Way,” which reached number 27 on the charts that year) of songs most closely identified as “ballad-rock” or “contem-pop” during the1960s Reprise era. As Friedwald writes, this formula became the “dominant mode” of future Sinatra singles and albums. 

On March 2, 1967, Sinatra’s efforts from the previous year were fully recognized. The song “Strangers in the Night” won Grammy’s in four different categories, including Record of the Year and Best Vocal Performance, Male. Sinatra at the Sands won Stan Cornyn the award for Best Album Notes. And, in an exquisite twist of fate, Strangers did not win Best Album honors. Instead, exhibiting a bizarre sense of humor, Grammy voters awarded Sinatra: A Man and His Music (an album issued in 1965, too late for inclusion in the 1966 Grammy nominations) that distinction.  

Five years before a self-imposed “retirement,” and two decades before becoming a caricatured figure, Frank Sinatra was at the height of his artistic and commercial appeal in 1966. You can almost still see him, impeccable, with a lit cigarette and tumbler of whiskey, as he might have described that year in his own unique vernacular: “Oh, it was a gas.”

James P. Freeman is a New England-based writer and  a former columnist with The Cape Cod Times