Although he’s best known as a singer, Frank Sinatra--who would today have celebrated his 100th birthday (if he hadn’t died in 1998)--managed to find time during his decades-long career to act in both movies and on television. In addition to his roles as a heroin addict in The Man With The Golden Arm (1955), a wise-cracking, second-rate singer in Pal Joey (1957), a war veteran turned casino robber in Ocean's Eleven (1960), and a suspicious army major in The Manchurian Candidate (1962), he appeared in several works of crime fiction.
The intro and opening scene from Contract on Cherry Street.
For instance, Sinatra twice starred as Marvin H. Albert’s “hard-living, hard-loving” Miami private eye, Tony Rome, first in the 1960 big-screener Tony Rome and then in 1968’s Lady in Cement. Also in ’68, he showed up as New York City police investigator Joe Leland in The Detective, based on Roderick Thorp’s 1966 novel of that same name. Almost a decade later, in 1977, Sintra played another Manhattan cop, Deputy Inspector Frank Hovannes, in the NBC-TV movie Contract on Cherry Street, which Wikipedia says is often cited as his “one starring role in a dramatic television film.” And in The First Deadly Sin (a 1980 picture adapted from Lawrence Sanders’ 1973 novel), he portrayed a troubled New York City homicide cop, Captain Edward X. Delaney. His last screen role, according to the Internet Movie Database (IMDb), was as retired police sergeant Michael Doheny in a 1987 episode of Tom Selleck’s Magnum, P.I. A note in IMDb maintains that Sinatra “planned to appear on Magnum, P.I. again the following season, but Tom Selleck’s scheduling conflicts forced the producers to cut back the episodes and Sinatra’s turn never came.”
READ MORE: “Mystery History -- The Crime Films of Frank Sinatra,” by Patrick Balester (Picks by Pat); “Frank Sinatra’s Centennial,” by Terence Towles Canote (A Shroud of Thoughts); “Frank Sinatra: A Hundred Years On, the Voice Resonates Still,” by Stephen Holden (The New York Times).