Trivia

Frank Sinatra said that he knew a girl that used to date bullfighters, a reference to his ex-wife Ava Gardner's affair with a matador when filming The Barefoot Contessa (1954) in Spain.

The character Tony Rome appeared in three novels by Marvin H. Albert in the early 1960s: "Miami Mayhem" (filmed as Tony Rome (1967)), "Lady in Cement," and "My Kind of Game."

The film finished shooting within six weeks and producer Aaron Rosenberg's assistant Michael Viner oversaw post-production. At the end of the film, there were a couple of problems involving Frank Sinatra according to Viner. "One night, he was so mad at the scriptwriter, he ripped a fire ax out of its casing and chopped down the door to his room, which cost a few hundred dollars. Then there was a prostitute who complained that Sinatra and his pals had not treated her quite right. She said that after an all-night party, Sinatra had invited her to stay for breakfast and called for an order of ham and eggs, which he then ate off her chest with a knife and fork. She threatened to sue Twentieth Century Fox because of that incident, but they settled before it got to court."

When Tony Rome gets in the taxi by the airport, on the side of the cab, there is an advertisement for fellow "Rat Pack" member Dean Martin's restaurant on the 79th Street Causeway.

The trauma of divorcing his young wife Mia Farrow hit Frank Sinatra hard early in 1968 while filming this movie in Florida during the day, and performing a stage show at the Fontainebleau at night. Refusing to do more than one take, and ripping out handfuls of the script to save time, Sinatra allegedly treated director Gordon Douglas like a lackey who was on the film simply to accommodate him. He further insisted that Douglas schedule his scenes so that he never had to come to work before noon, the sets be pre-lit, and for his stand-in to have plotted every move so that by the time Sinatra arrived he could complete action on one set and proceed to the next without delay. This was the fifth film he made with Douglas as his director and it was - perhaps not surprisingly - the last.