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Showtime's ‘Stealing Sinatra’ is wacky fun

William H. Macy and David Arquette star as the bumblers who decide to kidnap the famous crooner's son.
/ Source: Hollywood Reporter

Showtime’s “Stealing Sinatra” is the rare TV movie that attempts to actually be funny — and more rare still, it often succeeds.

The semi-dark comedy, which recounts the loopy 1963 kidnapping of Frank Sinatra Jr. by a trio of born losers, has moments of sheer inspiration thanks to a divertingly offbeat teleplay by Howard Korder and a typically sublime performance by William H. Macy as a highly principled kidnapper. This may be Macy’s most cannily entertaining work since his Oscar-nominated turn in “Fargo,” coaxing from him a similarly deadpan style that vividly illustrates a man on the cusp of madness.

David Arquette also comes through with a memorable turn as Barry Keenan, the sad-sack would-be entrepreneur whose idea it was to snatch Frank Sinatra’s 19-year-old son at gunpoint from a Lake Tahoe motel and hold him for a $240,000 ransom. The story line of how the three rank amateurs bungled things is said to be culled from actual trial transcripts of their prosecutions. The case has always been steeped in a mystery that challenges the actual legitimacy of the kidnapping itself. Some claim to this day that it was a hoax designed to help the painfully insecure Junior summon a bit of public notoriety/sympathy. That only pity and humiliation followed in its wake remains the tale’s true legacy.

In fact, history treats the abduction as scarcely a footnote — at least in part because the kidnappers were so uncommonly lame and no physical harm came to Sinatra Jr. And clearly, the only way you could have made a movie about this mess is to do it the way that scribe Korder and director Ron Underwood (“City Slickers”) did it: with a wink and a nod (maybe several nods).

The take, which takes place absurdly enough amid the backdrop of President Kennedy’s assassination, finds Keenan (Arquette) broken by the falling-through of his latest harebrained scheme. So he hatches the insipid idea to snatch Sinatra Jr. and use the resulting ransom cash as seed money to fund additional desperate ventures. Why Junior? There is an allusion here to some misguided tie to Sinatra’s daughter Nancy and swim champion-turned-Tarzan Johnny Weissmuller. But it’s as unclear as the unformed plan itself.

Keenan is able to coerce old classmate Joe Amsler (Ryan Browning) into this fiasco along with John Irwin (Macy), Keenan’s alcoholic mother’s alcoholic ex-boyfriend (got all that?) and a man with remarkable morals and ethics for a chemically dependent wing nut. The film builds wacky steam as it moves along, with Keenan and Amsler sniping at each other and the alcoholic providing the so-called stability. It’s simply a bravura performance for Macy, who out and out steals the show. He counsels Junior on life and keeping faith in himself even as he readjusts the prisoner’s blindfold.

“Stealing Sinatra” moves through its straight-faced paces with a certain bizarre assuredness. A postscript flashed onscreen tells us that while all three men wound up serving prison time, all were ultimately paroled in the late 1960s — and Keenan became the multimillionaire he’d always hungered to be. Talk about sweet irony. If the film is less docudrama than off-kilter character study, that’s OK. Just don’t go into it expecting necessarily to learn what really happened.

“Stealing Sinatra” airs Sunday at 8 p.m. on Showtime.