Frank Sinatra and Jill St. John beachside at the Fontainebleau, in a scene from Tony Rome, 1967.

True to the lyrics of his recent hit “That’s Life,” Frank Sinatra was riding high in April 1967. He’d just scored his second consecutive Grammy for album of the year and had been the subject of numerous television specials and magazine profiles marking his 50th birthday, an occasion that, to hear some tell it, rated just behind World War II as an event of national significance. And he was in love again, officially this time, having married 21-year-old Mia Farrow a few months earlier.

Now he was blowing into Miami Beach to star in Tony Rome. It was just the kind of tough-guy fare Sinatra liked. In the film, he’d play the title character, a private eye who gets sucked into a complex mystery involving stolen jewels, blackmail and a wealthy family with too many secrets. It wasn’t Oscar-caliber stuff—Sinatra already had a statue, anyway—but it was a solid story, and filming on location in South Florida promised to be an entertaining change of pace.

By this time, making movies for Sinatra had largely become an excuse to gather his friends, and Tony Rome was no different. The cast included onetime flame Jill St. John, Ocean’s Eleven sidekick Richard Conte and parttime- actor pals like former middleweight boxing champ Rocky Graziano and legendary Hollywood restaurateur “Prince” Mike Romanoff. For Romanoff, whose eponymous eatery had been a hot spot for Tinseltown royalty in the ’40s and ’50s, Sinatra not only secured a bit part in the film—playing, naturally, a restaurant host—but also a gig as the producer’s assistant.

“They followed Sinatra around,” says South Florida casting agent Beverly McDermott, speaking of colorful characters like Graziano and Romanoff. The same could be said of director Gordon Douglas, an old Hollywood hand with a mostly undistinguished track record, except for the fact that he made five movies with the singer. (Tony Rome was the third.) “They were drinking buddies,” remembers Deanna Lund, who had a small, memorable role as a lesbian stripper. “[Douglas] let Sinatra pretty much do what he wanted.”

Sinatra shot his scenes during the day, shuttling between locations like Vizcaya, the 5th Street Gym and seedy bars and motels on old South Beach. At night, he played to a packed house at the Fontainebleau’s La Ronde nightclub, with members of the cast and crew—most of whom stayed at the hotel during the five-week shoot—in attendance. “He arranged ringside seats for us every night,” says McDermott.

Onstage, Sinatra would sip Jack Daniel’s and run through a dozen or so of his signature songs, mixing a little Rat Pack humor in between. One gag involved sitting on a stool that had a seat belt. “The last time I was here, I fell off,” he informed the audience. Then, for those who didn’t quite catch his drift: “I’m bombed!”

To the casual observer, the whole thing was a nonstop party. In reality, for Sinatra, it was anything but. His marriage to the free-spirited Farrow was already showing signs of discord. “I can’t live off Frank’s laurels,” she’d told a reporter in February, before taking off for Europe to begin work on a new movie, A Dandy in Aspic. “I’ve got to do things on my own.”

LEFT: Sinatra with crony, bit player and Hollywood restaurateur “Prince” Mike Romanoff.

Her decision apparently didn’t sit well with her husband. “I saw him on the phone a few times when he got pretty upset,” recalls Lund. Perhaps to get his mind off his wandering bride, Sinatra threw himself into Tony Rome. “Sinatra worked hard, and always knew his lines,” says acclaimed actress Gena Rowlands, a costar. “I found it very easy to work with him.”

Lund agrees, and recounts one particularly touching moment on the set: “After we finished our scene [in which Rome barges in on Lund’s character, home undressing after a late night out], I was down to my underwear. He came over and put a robe around me. He was just a charmer.”

There was, though, a flip side to Sinatra’s gallant displays—a dangerous one. “He had these steely blue eyes and he’d look around [the set] and spot anybody who didn’t belong there,” says Beverly’s husband, Jack McDermott, a radio personality who spent time around the production. The penalty for angering Sinatra could be severe, as comedian Shecky Greene discovered. In a wellpublicized incident, Greene—who, in addition to playing one of the bad guys in Tony Rome, was also Sinatra’s opening act at the Fontainebleau— somehow ran afoul of his host and was subsequently ambushed by some men in the hotel lobby. The beating landed the comic in the hospital. “[Sinatra] did what he wanted and had a couple of big guys [around] to help him do what he wanted,” is all Lund will say about that and similar episodes reported at the time.

Soon after filming wrapped, Sinatra would be romantically linked to a beautiful young starlet named Tiffany Bolling, who made her debut in the film. The relationship wouldn’t last. Neither would Sinatra’s midlife marriage to Mia; they were divorced a year later.

Tony Rome had its world premiere at the Carib Theatre on Lincoln Road in late 1967. Sinatra would return to Miami Beach the following year to reprise his role as Tony Rome in Lady in Cement. It was the old routine—shoot during the day, play the Fontainebleau at night. But somehow things just weren’t the same. Hard-boiled private eyes, with their armor of certainty, were more than a little out-of-date in the Age of Aquarius. Musical styles were changing, as well, and not even “The Voice” could drown out the siren song of the Beatles, Hendrix and Dylan. His choke hold on popular taste was slipping.

Sinatra had made turning 50 look like a lot of fun. Being 50, he was discovering, was a different matter. From the balcony of his penthouse at the Fontainebleau, staring out over the water, the past must have seemed like a distant land—and the future, the greatest mystery of all.

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