To begin with, I recall catching the opening sequence of this one as a kid on a now-defunct Sicilian TV channel Considered the best of the Rat Pack films, this is a slick, likable and witty transposition of the Robin Hood legend to gangland Chicago. A generally bright outing, it loses steam towards the end, emerging as being decidedly overlong.
The stars are in their element – Frank Sinatra is Robin (called Robbo and clearly relishing the role, it’s hard not to be reminded of the star’s real-life mob connections), Dean Martin is Little John (their famous initial confrontation takes place over a game of pool!), Sammy Davis Jr. (who does a fair imitation of James Cagney) is Will Scarlett and Bing Crosby turns up half-way through as Allen A. Dale (this proved to be his last musical role). As for the villains, Peter Falk is wonderful as Guy Gisbourne (though he seemed stuck in gangster types during this time in his career) and heavy-set cocoa-drinking Victor Buono is the new Sheriff. However, I think it was a mistake to present Marian (Barbara Rush) as a femme fatale; appropriately, then, Edward G. Robinson (an icon of the gangster genre) cameos as Big Jim – the Richard the Lionheart figure. There are also notable bits by Hans Conried (as Robbo’s put-upon architect), Allen Jenkins (as a disgruntled partner of Falk’s) and Sig Ruman (as a leading citizen).
Though OCEAN’S 11 (1960) did provide a title tune sung by Davis, this is the only Rat Pack musical of the lot. Sinatra’s “My Kind Of Town” was nominated for an Oscar – but other songs are actually more memorably presented: Davis’ own energetic destruction (at the rhythm of a tap dance) of Falk’s gambling joint; “Style”, a momentous collaboration between Sinatra, Martin and Crosby (three of the best-loved crooners ever); and Crosby’s show-stopping “Mr. Booze” (at one point, to divert a police raid organized by rival Falk, Robin’s gang turns the joint into an impromptu temperance meeting!). With this in mind, the film has definite black comedy touches – particularly in the cornerstone-laying motif. However, the Christmasy finale in which the tables are once again turned in favor of Robbo and Rush is reformed (off-screen) by Crosby feels rushed.
Some trivia connected to the film: a kidnapping scene was dropped for hitting too close to home – Sinatra’s own kid had just been abducted and eventually ransomed for $250,000!; on the day JFK was shot dead, the scene of Robinson’s funeral was being filmed!; apparently, Sinatra’s old musical pal Gene Kelly was originally involved in the production as a dance director but left during its early stages after disagreeing with Sinatra (who also served here as producer) over the number of dance routines to be incorporated into the film.