Meet Me in St Louis (1944)
Although six-year-old Margaret O'Brien ("Tootie") steals every scene she's in, Judy Garland is the obvious star in this love letter to the city that is the home of the Gateway Arch, and was the host to both the World's Fair and the Summer Olympics in 1904 (though the latter is not mentioned in the film, probably because the Fair completely overshadowed the Games).
The story is based on the real-life experiences of novelist Sally Benson, whose book was serialised in The New Yorker in 1942. Like the fictional Smith family, Benson's family moved from St Louis to New York City. The Bensons, though, left before the World's Fair started and didn't return.
Meet Me in St Louis features some now-classic tunes including The Trolley Song and Have Yourself a Merry Little Christmas, both sung by Garland in her inimitable style. It was directed by Vincente Minnelli, who met Garland on this film and married her right after.
