The story follows the adventures of Miami private investigator Tony Rome (Sinatra) in his quest to locate a missing diamond pin that belongs to a wealthy heiress, Diana (Lyon), the daughter of rich construction magnate Rudolph Kosterman, and her stepmother Rita (Rowlands), while also getting help from a seductive divorcee, Ann Archer (St. John).
A sequel, Lady in Cement, was released in 1968, again featuring Sinatra as Rome.
This film features examples of:
- Deadpan Snarker: Rome, as befitting of a Hardboiled Detective played by Frank Sinatra.Diana: People change. They don't always turn out the way you expect.Tony: I know. You should see my baby pictures.
- Did Not Get the Girl: At the end, Ann leaves Rome after she decides to go back to her husband.
- Double Entendre: Rome holds a long conversation with his neighbor Mrs. Schuyler about her cat... who they both insist to refer to as a "pussy".
- Lipstick Lesbian: Rome meets an attractive, very femenine stripper... who is revealed to have a much older (and much more butch) female "roommate". Their subsequent argument when the stripper arrives home with Rome leaves no doubt about the true nature of their relationship.