The Lemon Drop Kid is a 1951 comedy film based on the short story of the same name by Damon Runyon, starring Bob Hope and Marilyn Maxwell, and directed by Sidney Lanfield.
The Lemon Drop Kid (Bob Hope), a New York City swindler, is illegally touting horses at a Florida racetrack. After several successful hustles, the Kid comes across a beautiful, but gullible, woman intending to bet a lot of money. The Kid convinces her to switch her bet, employing a prefabricated con. Unfortunately for the Kid, the woman "belongs" to notorious gangster Moose Moran (Fred Clark), as does the money. The Kid's choice finishes dead last and a furious Moran demands the Kid provide him with $10,000 (the amount he stood to win with his original bet) by Christmas Eve, or the Kid "won't make it to New Year's."
The Kid decides to return to New York to try to come up with the money. He first tries his on-again, off-again girlfriend Brainy Baxter (Marilyn Maxwell). However, when talk of long-term commitment arises, the Kid quickly makes an escape. He next visits local crime boss "Oxford" Charley (Lloyd Nolan), with whom he has had past dealings. This falls through as Charley is in serious tax trouble and does not particularly care for the Kid anyway. As he leaves Charley's establishment and is about to give up hope, the Kid notices a cornerside Santa Claus and his kettle.
Thinking quickly, the Kid fashions himself a Santa suit and begins collecting donations. This fails as he is recognized by a passing policeman, who remembers his previous underhanded activity well. The Kid lands in court, where he is convicted of panhandling and sentenced to ten days in jail (as he cannot pay his fine). However, while in court, the Kid learns where his scheme went wrong. After a short stay, Brainy arrives to bail him out. He then sets about restarting his Santa operation, this time with legitimate backing. To this end, he needs a charity to represent and a city license. The kid receives key inspiration when he remembers that Nellie Thursday (Jane Darwell), a kindly neighborhood resident, has been denied entry to a retirement home because of her jailed husband's criminal past as a safecracker.
Organizing other small-time New York swindlers and Brainy, who is both surprised and charmed at the Kid's apparent goodwill, the Kid converts an abandoned casino (ironically belonging to Moose Moran) into the "Nellie Thursday Home For Old Dolls". A small group of elderly women and makeshift amenities complete the project. The Kid is able to receive the all-important city license. Now free to collect, the Kid and his compatriots dress as Santa Claus and position themselves throughout Manhattan. The others are unaware that the Kid plans to keep the money for himself to pay off Moran. The scheme is a huge success, netting $2,000 in only a few days. An overjoyed Brainy decides to leave her job as a dancer and look after the "home" full-time until after Christmas. Coincidentally, her employer is none other than "Oxford" Charley, whom Brainy cheerfully informs of the effort.
Seeing a potential gold mine, Charley decides to muscle in on the operation. Reasoning that the Nellie Thursday home is "wherever Nellie Thursday is", Charley and his crew kidnap the home's inhabitants (including Nellie and Brainy) and move them to Charley's mansion in Nyack. The Kid learns of this when he returns to the home after a late night to find the home deserted and money (which he had hidden in a hollowed-out statue) gone. Clued in by oversized Oxford footprints in the snow, the Kid and his friends pay Charley a visit. Here, Charley reveals the true nature of the Kid's scheme through a phone conversation with Moose Moran. The Kid's accomplices are angry and move to confront him, but the Kid manages to slip away. However, Brainy tracks him down outside and voices her disgust at his actions.
After a few days of stewing in self-pity (and realizing it is Christmas Eve), the Kid is surprised to meet Nellie, who has escaped Charley's compound. He decides to recover the money, sneaking into Charley's home in the guise of an elderly woman. He finds that Charley and his crew are again moving the women, this time to a more secure location. Using the heightened activity to his advantage, the Kid enters Charley's office and confronts him. After a brief struggle, the Kid overpowers Charley and makes off with the money, narrowly avoiding the thugs Charley has sent after him. The ensuing chaos allows Brainy and the others to escape.
Later that night, the Kid returns to the original Nellie Thursday home to meet with Moose Moran (who has returned home for the holidays). The deal appears to be in jeopardy as Moran arrives with Charley. Charley demands that the Kid reimburse him, which would leave too little for Moran. However, the Kid turns the tables by hitting a switch, revealing hidden casino tables. All are occupied, mainly by the escaped old dolls. The Kid and his still-loyal friends hold off the gangsters as the police initiate a raid. Moran and Charley are arrested while the judge who sentenced the Kid earlier warns that he will be "keeping an eye on him". The Kid assures him that will not be necessary and his attention will lie on the home, which is going to become a reality. The night's main event begins as Nellie's husband Henry, free on parole, joyously reunites with his wife.
Sidney Melbourne: Santy Claus don't drink.
Gloomy Willie: Oh, no? Well, how come he's always falling down chimleys?
Sidney Melbourne: Santy Claus don't drink. Gloomy Willie: Oh, no? Well, how come he's always falling down chimleys?