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When writing the script for Meet Me in St. Louis, Irving Brecher left a spot for a song when Judy Garland and company travel on the trolley.

“This might be a good place for a song,” he wrote. Producer Arthur Freed agreed and asked writers Hugh Martin and Ralph Blane to write one.

“I really thought he wanted a song that was like ‘Cuddle Up a Little Closer’ or ‘Play that Barbershop Chord.’ Something from that period that Judy could show off doing. I didn’t know he wanted a song about the trolley because Arthur was a little inarticulate,” Martin recalled.

The duo wrote three songs that they thought would work perfectly, but Freed tossed all of them out. He didn’t want a song for the trolley ride, he wanted a song about the trolley.

While the songwriters felt that was too on the nose, they did it anyway.

“And how right he was. That man had an infallible sense of decisions and judgements,” said Martin.

The song was actually inspired by a picture of an old trolley which had the caption: “Clang! Clang! Clang! went the jolly little trolley.”

Once they had that line, the pair knew what to write and were performing it for Freed approximately three hours later.

Since MGM didn’t have a trolley to shoot the sequence on, the studio had one built. The aisles were made wide enough for the cast to move about freely and the structure was built sturdy enough for dancing. The choreography took 16 days to work out.

 “We actually rocked and rolled on this trolley. By the time you got off of it, you couldn’t walk. You looked drunk,” actress Dorothy Raye recalled. “[Judy] really seemed to enjoy it. She actually laughed a great deal of the time because it was fun.”