In the Good Old Summertime (1949)

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Rotten Tomatoes® Score
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In this musical romance, lovely Veronica Fisher (Judy Garland) lands a job in Otto Oberkugen's (S.Z. Sakall) music store in turn-of-the-century Chicago.

Though the other employees like her, including Otto's clumsy nephew Hickey (Buster Keaton), salesman Andrew Larkin (Van Johnson) -- who is threatened by her competition, and secretly attracted to her -- greets her coolly. Each of them is carrying on a romantic correspondence with an as-yet-to-be-met pen pal. They are both in for a surprise.