The 1967 film, Tony Rome, is about a detective named …. can you guess it?

That’s right! Tony Rome!

Tony works out of Miami and, because he’s played by Frank Sinatra, you can be sure that he’s a tough guy who knows how to throw a punch but who, at the same time, also knows how to have a good time. He’s got a bottle of liquor in the glove compartment. He’s got his own boat. He’s got a snappy quip for every occasion and a properly cynical sense of humor but at the same time, he also cares about doing the right thing. He says what’s on his mind and if that hurts your feelings, tough. Again, none of this should be a surprise, considering that he’s played by Frank Sinatra and Sinatra could play these type of sentimental tough guys in his sleep.

That’s not to say that Sinatra sleepwalks through the role, of course. Far from it. As played by Sinatra, Tony comes across as an authentic tough guy, as someone who has seen it all and who, as a result, understands that importance of stopping to have a drink and appreciate the world around him. Tony Rome might be a Rat Pack-style private investigator but that doesn’t mean he can’t solve the case and, even while Tony’s having a good time, Sinatra never lets you forget that he takes his job very seriously.

As for the film, it’s a story that beings when Tony is hired to drive a passed out rich girl back to her home. This leads to him investigating a jewelry theft and eventually discovering an extortion plot. Sue Lyon plays the rich girl. Gena Rowlands plays her stepmother while Simon Oakland (the psychologist at the end of Psycho) plays her father. Richard Conte, who played bad gangster Barzini in The Godfather, plays Tony Rome’s best friend on the police force. (Every good private eye has a best friend on the police force.) Jill St. John plays Ann Archer, who helps Tony out with his investigation. Ann is recently divorced. Will Tony claim her heart or will she go back to her husband? It wouldn’t be a Sinatra film without a little heartbreak. (To a large extent, St. John’s performance here feels like a slightly more serious version of the performance she would later give as Tiffany Case in Diamonds are Forever, which is perhaps as close as we’ll ever get to a Rat Pack-style James Bond film.)

The story itself is surprisingly easy to follow. This is not one of those detective stories that will leave you shocked over who turns out to be the bad guy. For a film that often takes something of a light-hearted approach to Tony’s efforts to solve the mystery, it’s also a rather violent film. More than a few people get killed. Tony gets kicked in the ribs at one point and the sound of the 50-something Sinatra groaning in pain is disconcerting. Of course, Tony recovers quickly and immediately gets his revenge. When you watch the scene, you think to yourself that anyone who would try to beat up Frank Sinatra has to be a fool. That’s largely because Tony is Sinatra and Sinatra is Tony.

It’s an entertaining film, one that works well as a time capsule of what it was like to cool and swinging and middle-aged in 1967. Tony Rome is smart enough to focus more on Sinatra’s charisma than on trying to impress the viewers with its own cleverness. If I ever have to hire a private detective, I hope he’s like Tony Rome. I hope he gets the job done. I hope he has a good time while doing it. And I hope he comes with his own Nancy Sinatra-sung theme song. That’s not too much to ask, is it?