This is the cover to the sheet music for The Trolley Song, from the MGM film Meet Me in St Louis (1944).
It was directed by Vincente Minnelli, which is how he and Judy Garland met, and later married.
It was the second-highest grossing film of the year and is deemed 'culturally significant' by the Library of Congress.
In this film, Garland debuted The Trolley Song, The Boy Next Door and Have Yourself a Merry Little Christmas, all of which became standards and remain well-known songs.
Condition: It needs a little work and a restorer can fix it up. This image is a scan, so it is as you see it.