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According to Stephen Bogart, the original members of the Holmby Hills Rat Pack were: Frank Sinatra (pack master), Judy Garland (first vice-president), Bacall (den mother), Sid Luft (cage master), Bogart (rat in charge of public relations), Swifty Lazar (recording secretary and treasurer), Nathaniel Benchley (historian), David Niven, Katharine ...
As far as the casting of Marlon Brando, otherwise not known for his singing abilities, Frank Sinatra and Jean Simmons, seem to work in the film. Sky Masterson is, after all, a man's man, who would look otherwise sissy if he presented a different 'look'. Frank Sinatra is good as Nathan Detroit.