Pal Joey (1957)
For Frank Sinatra, riding high as an actor and a singer in 1957, the chance to play Joey Evans in the screen adaptation of the Broadway musical Pal Joey must have seemed irresistible, because Joey is nothing less than a failed Frank Sinatra. He's a saloon singer who bounces from town to town, dame to dame, always hungry for the big time but too much of a heel and a phony to ever make it. Then Joey hits San Francisco and runs smack into stripper-turned-rich society widow Vera Simpson (Rita Hayworth); after giving Joey the brush off, she falls victim to his street-smart charms, especially after he warbles "The Lady Is a Tramp." Vera sets the crooner up in the swankiest nightclub on Nob Hill, to be called (what else?) Chez Joey, while also installing him on her lavish houseboat. But romantic conflict presents itself in the lovely form of Linda English (Kim Novak), a nice gal from the sticks who's trying to make it as a "mouse on the line" (chorus girl). Will Joey be a kept man, complete with a fully monogrammed wardrobe, or go for true love? Hey, it was the '50s, so you can probably guess the ending. But with gorgeous location photography, a Richard Rogers score, and three terrific lead performances, Pal Joey is a gloriously artificial artifact from Hollywood's past.