Frank Sinatra’s Miami

Frank Sinatra was America’s original hipster, jiving to original tunes and rocking fedoras long before those Wynwooders. He brought his swagger to our Magic City with his frequent visits during the 1960s, an era that was perhaps the height of his fame.

Sinatra: An American Icon,” a traveling exhibit honoring what would have been the iconic singer and actor’s 100 birthday, reached Miami on Thursday. HistoryMiami will be hosting the exhibit, which is stopping in Sinatra’s most beloved cities around the world.

It’s incredibly intimate, featuring old home movies and Sinatra’s own Grammy, Golden Globes, and Oscar awards. His clothes are also on display, with showcases housing one of his tuxedos, two pairs of shoes worn by him and and actress Grace Kelly, and even a set of his pajamas.

While the Sinatra family was hesitant to allow such valuable objects out of their sight, when they finally agreed to a traveling exhibition, they wanted to ensure that Miami was a city on the circuit, according to Chris Morrison, the traveling exhibitions manager for the GRAMMY Museum, the host of the exhibit.

A familiar tropical paradise, Sinatra loved the Miami sun — frequenting hotels like The Fontainebleau and The Eden Roc on Miami Beach. Sinatra caused a great stir everywhere he went and was often trailed by hordes of adoring fans when he walked around the city.

“Miami played a very prominent role in his career and life,” said Stuart Chase, president and CEO of HistoryMiami. “Sinatra loved coming here and visiting. He lived in Palm Springs, Calif., but his second favorite place was Miami, followed by the south of France.”

HistoryMiami has curated a local addition to the exhibit, showcasing Miami as Sinatra experienced it. It includes movie posters from local shoots of Tony Rome, A Hole in the Head, and A Lady in Cement. It also catalogs Sinatra’s stays at The Eden Roc and The Fontainebleau — two of his frequent Magic City haunts.

Join us on a gallivant through Sinatra’s Miami.

The Fontainebleau

The soaring Fontainebleau on Collins Avenue was one of Sinatra’s favorite places to stay and perform. The singer regularly played to a full house at the hotel’s La Ronde Supper Club, on the stage that is now part of LIV nightclub. Sinatra often performed alongside other members of The Rat Pack – legends like Sammy Davis Jr., Dean Martin, Peter Lawford, and Joey Bishop.

Sinatra frequently performed with African-American legends like Davis and Count Basie. As a champion of equality, Sinatra emphatically refused to stay at places that discriminated against others on the basis of race or religion.

“He was working in a time of great prejudice and had very successful [black] artists and musicians who worked with him,” Chase said.

Sinatra felt so passionate about this that he opened his own golf course, the Tamarisk Country Club, in his hometown of Palm Springs. The club explicitly did not discriminate on the basis of race or religion — the first of its kind in the area.

The Fountainebleau reps its Sinatra connection hard. If you’re feeling nostalgic for Ol’ Blue Eyes, you can go to their nightly toast or breakfast inspired by him.

The Eden Roc

Sinatra stayed and performed many times at The Eden Roc, another Collins Avenue stalwart, most notably during a two-week stretch from Feb. 1 to 14 in 1965 when he was also filming at the hotel.

Sinatra and Joe E. Lewis, an American comedian and singer from New York, played at “The Roc,” as local hipsters called the hotel then, to a sold-out 1,800-person audience each night, according to a news clipping from the time.

His love for Jack Daniels

Sinatra was known to have a particular affinity for Jack Daniels — a love he was introduced to by comedian Jackie Gleason, another famous Miami name.

Rumor has it that Sinatra and Gleason were sitting at a Manhattan bar talking about their love lives. Sinatra, who was married four times, had his fair share of wounds to heal with a prescription of a little liquid lovin’. Gleason told Sinatra to try Jack to mend his bruised heart, and the rest was history. Sinatra loved Jack Daniels so much he was buried with a bottle of it, according to Morrison. He was also buried with a roll of dimes because he believed that a person should always be prepared to make a phone call.

Filming Tony Rome and The Lady in Cement

While filming the 1967 Tony Rome, the first of a crime drama trilogy, Sinatra spent time all over Miami-Dade.  Sinatra’s character was a tough private investigator who lived on a houseboat in Key Biscayne and was hired by a local millionaire living at the Vizcaya Museum and Gardens to find stolen jewelry. The gig led to encounters with local gangs and the Miami Beach Police Department and took Sinatra on a tour through Miami, including a boat chase along Miami Beach and the famous South Beach 5th St. boxing gym. The series’ sequel, The Lady In Cement, was also filmed in Miami, while the third, The Detective, was filmed in New York.

Filming A Hole in the Head

Sinatra plays a widower struggling to run a Miami Beach resort called The Garden of Eden in the 1959 comedy A Hole in the Head. Hotel scenes were shot at the Cardozo Hotel in South Beach, which still functions as a hotel today. The movie was adapted from a play written by Arnold Schulman, a playwright whose father actually operated a hotel in Miami.

And so, as we look back on Sinatra’s incredible legacy, it’s clear that Miami and Miami Beach had a formidable impact on the legendary singer and actor’s career. As he so beautifully sang, “he lived a life that was full, traveled each and every highway,” and more than this — he did it his way.