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.”

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