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Damon Runyon's story Little Miss Marker gets a mid-'60s update in this comedy. Steve McCluskey (Tony Curtis) is the manager of a nightspot in Lake Tahoe owned by Bernie Friedman (Phil Silvers).
Steve is the kind of guy who has heard every sob story in the book and is not easily impressed, but his hard heart begins to soften a bit when he meets Penny Piper (Claire Wilcox), a young orphan girl with no one to turn to and nowhere to go. Steve grudgingly takes her in and soon grows fond of the tyke.
Penny thinks that Steve needs to get married and settle down, so she starts playing Cupid, trying to set him up with pretty Chris Lockwood (Suzanne Pleshette). However, Steve is still reeling from his failed first marriage and isn't so sure that another trip to the altar would be good for him.
The film's finale sends Steve on a wild chase through Disneyland. Forty Pounds of Trouble marked the feature directorial debut of Norman Jewison, who would go on to make In the Heat of the Night, Fiddler on the Roof, and Jesus Christ Superstar.