Buster Keaton was working as a gag writer at MGM when this movie was made. The filmmakers approached him to devise a way for a violin to get broken that would be both comic and plausible. Keaton came up with an appropriate fall, and the filmmakers then realized he was the only one who would be able to execute it properly, so they cast him in the film. Keaton also devised the sequence in which Van Johnson inadvertently wrecks Judy Garland's hat, and coached Johnson intensively in how to perform the scene. This was the first MGM film Keaton appeared in since being fired from the studio in 1933.
Liza Minnelli appears in the final scene. She's the "Babe in Arms" held by Andrew Delby Larkin (portrayed by Van Johnson) and Veronica Fisher (portrayed by her mother, Judy Garland), as the credits start to roll, "The End; Made in Hollywood, U.S.A. by Metro-Goldwyn-Mayer". It was Liza's (uncredited) film debut.
Marcia Van Dyke who played Louise Parkson was an accomplished violinist and did all her own playing in the film.
Charles Smith, who plays an uncredited role as a member of the barbershop quartet also played the role of Rudy in the The Shop Around the Corner (1940), an early version of the storyline for this movie.
The original story of anonymous romantic correspondence between antagonistic coworkers came from "Parfumerie," a 1937 play by Hungarian playwright Miklos Laszlo. Ernst Lubitsch loved the story and bought the rights to the play, eventually adapting it for the big screen as "The Shop Around the Corner" (1940) with Jimmy Stewart and Margaret Sullavan. The same story was then remade as the movie musical "In the Good Old Summertime" (1949) with Van Johnson and Judy Garland, and later as the contemporary rom-com "You've Got Mail" (1998) with Tom Hanks and Meg Ryan.