Stealing Sinatra is an oddball and slightly dark comedy that was unjustly overlooked on release, perhaps because director Ron Underwood had been responsible for a series of middling-to-woeful comedies such as City Slickers and his previous film, The Adventures of Pluto Nash.
Based on the true story of the kidnapping of Frank Sinatra Jr in 1963, on the same day as the assassination of President JFK, Stealing Sinatra follows the story of three none-too-bright guys well out of their depth in their attempt to get rich quick.
David Arquette (who looks like a plumper version of our own Will Anderson), plays Barry Keenan, a delusional young man with ambition but no talent who went to college with the children of celebrities and who suffers from success envy. He embroils an old friend from the same school, dumb-as-a-box-of-rocks Joe Amsler (Ryan Browning) in his plan to kidnap Frank Jr (Thomas Ian Nicholas) whilst his mother’s sad-sack boyfriend, Mr Irwin (William H. Macy) joins in because he feels obliged to save Barry from himself.
The three leads are excellent. Arquette bubbles with good-natured enthusiasm for his scheme oblivious to its serious illegality and Macy is priceless as the chronically defeated self-styled father-figure who feels duty bound to help him whilst Ryan Browning does a nice turn with very little to round out the triple shot of incompetence.
Underwood’s film, despite its low profile credentials is surprisingly well made with delicious 1960s retro decor and wardrobe and a smartly economical script by Howard Korder that never loses its grip on its tongue-in-cheek élan. Despite this, the film sank like a stone and Underwood has worked in television ever since.