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MGM purchased the screen rights for On the Town for $250 thousand before even seeing the show. In fact, it was before Leonard Bernstein had even finished the score. An enthusiastic writer had heard bits of the music and convinced Louis B. Mayer that the show would be a hit.
Unfortunately, when the studio executives did see the musical on Broadway in 1944, they didn’t see its potential. Little did they know what producer Arthur Freed was going to do with it.
Co-director Stanley Donen said, “Arthur just had some sort of instinct to change the musical from the backstage world into something else… he really had a basic understanding of the musical film that no other film producer had.”
1. The musical was reworked for its star.

Betty Comden, co-writer of the film, said, “With Gene [Kelly] as the leading character and the star of the picture the angle of the story had to be changed. He couldn’t be a helpless, naïve type.” Additionally, Freed wanted new songs, rather than using Bernstein’s score.
2. The censors asked for lyric changes.

The original lyrics were “New York, New York/It’s a helluva town.” To avoiding swearing, "wonderful" was used instead. Censors also took issue with “Prehistoric Man” because Ann Miller would have sung “Lots of guys are hot for me” and “Libidio—I love that libido”. Both lines didn’t make the final cut.
3. They shot on location.

Gene Kelly wanted to film the entire movie on location. However, the budget wouldn’t allow for such an expense. The studio worked with the New York police and Department of Commerce in order to arrange shoots, traffic, and other logistics. This musical was the first to shoot in public spaces, and it was hard work to synch the movement, lip-synch, and dancing. Kelly said, “This was one of the things that changed the history of musicals more than anything.”
4. Kelly convinced Sinatra to take the part.

After Anchors Aweigh, Frank Sinatra said, “They’re not going to get me into another sailor’s suit!” Thankfully, Gene Kelly, who had worked with him on two other pictures, was able to talk him into donning the costume one more time. He also taught Frank and Jules Munshin how to dance in the film. They especially had fun doing moves alongside Ann Miller and Betty Garrett. Sinatra said, “Those girls could move – and they gave us a lot of oomph.”
5. They built a dinosaur.

The T-Rex was fifteen feet by forty feet by twenty-five feet. The creature was made in such a way that it could collapse and be put back together again. The crew also created the roof of the Empire State Building in a ten foot deep swimming pool to give it more height when filming.