In his later years, Gene Kelly held this film in very high regard. In one BBC interview he said something to the effect of, "We made better pictures than that, but that was the apex of our talent. That was it."
Ann Miller commented in a TCM interview that at least one take of her big tap number to "Prehistoric Man" was ruined because of her own costume. She had been dancing very close to the large dinosaur , and during a series of her trademark tap spins, the flared skirt she was wearing brushed against some of the bones and brought the entire exhibit crashing to the ground. Filming was halted for a considerable time while it was put back together.
Frank Sinatra, who was very thin, had to wear prosthetic padding to fill out the seat of his uniform. In a TCM interview, Ann Miller said that Sinatra was extremely sensitive about his padding and did not appreciate the usual movie set horseplay involving his lower half.
Arthur Freed, the producer of the film, sent a memo to Gene Kelly and Stanley Donen during shooting, saying, "I just ran the cut musical numbers of On The Town, and they were the greatest and most inspiring works I have seen since I have been making moving pictures. [Emeric] Pressburger and [Michael] Powell can't shine your shoes - red, white or blue. Much love from your proud producer."
A total of 5 days was spent filming in New York City. The 2 major problems faced by the crew was the weather (it rained for most of the shoot) and the popularity of Frank Sinatra. Gene Kelly explained that the movie was filmed at the height of Sinatra mania and Frank would be instantly recognized by people on the streets. To avoid crowds the cast insisted on taxis instead of limousines for transportation and that the camera be hidden inside a station wagon. During the finale of the "New York, New York" musical number, which takes place in the sunken plaza at 30 Rockefeller Plaza in front of the statue of Prometheus, you can see at the top of the frame of the last shot, the heads of hundreds of curious spectators staring at the three stars over the wall behind the statue.
There was a real-life version of the "Miss Turnstiles" contest in New York City. "Miss Subways" was a beauty contest run by the New York Subways Advertising Company from 1941 to 1976. Subway cars featured posters of pretty young women who lived and worked in New York.
Jules Munshin was terrified of heights. While performing on the tiny rooftop during the song "New York, New York" the only way he could perform the number was while one end of a rope was secured around his waist under his sailor suit. The other end of the rope was secured, off camera, to Stanley Donen. And even so, alert viewers of the scene will notice that during the scene Munshin is almost always touching a wall or a prop or another actor.
When On the Town premiered at Radio City Music Hall, the line to get in was the largest in that theater's history. After its initial success, Arthur Freed, the producer of the film recalled, his unit was in the MGM commissary passing the Joe Pasternak unit (which made less expensive musicals); one member of the Pasternak unit said, "There goes the royal family." Indeed, this movie was, at the time, the second largest-grossing in MGM history, next to Meet Me in St. Louis (1944).
According to information contained in the file on the film in the MPAA/PCA Collection at the Academy of Motion Pic Arts & Sciences Library, the Breen Office refused to allow the use of the word "helluva" in the song "New York, New York [it's a helluva town]." M-G-M later changed the word to "wonderful."
In On the Town (1949), Frank Sinatra co-sang "New York, New York". Years later, he used the song "Theme From New York, New York" (first performed by friend Liza Minnelli, and commonly referred to as simply "New York, New York") as a showstopper in his live performances. In his "Concert For The Americas" (1982) he combined the 2 songs using the first verse of the earlier song.
In her screen debut, Alice Pearce repeated her 1944 Broadway stage role as Lucy Shmeeler (the roommate with the unfortunate sneezing problem). Alice Pearce is also fondly remembered as the first actress to portray nosy neighbor Gladys Kravitz on TV's Bewitched (1964). Pearce was the only member of the original Broadway cast to appear in the film.
Arthur Freed had to convince Louis B. Mayer to purchase the movie rights of the hit Broadway musical. Mayer had criticized the stage production as "smutty" because of a scene in which a black woman danced with a white man.
This was the first musical feature film to be shot on location. In a TCM interview, Ann Miller took the credit for pleading and persuading Louis B. Mayer to do the shoot on location as she had "never seen New York".
Judy Holliday dubbed in the following line of dialogue for an uncredited bit player billed as Daisy: "The grass is always greener, if ya know what I mean." The line was designed to get a big laugh, but audiences didn't react to it in previews until it was dubbed by Holiday.
Before purchasing the film rights to the musical, M-G-M had assigned George Abbott, the director of the stage show, to direct the film version. However, Louis B. Mayer and other studio executives disliked the stage show when they saw it and regretted their involvement in the property. By November 1945, the studio had assigned Gene Kelly and Stanley Donen to direct the film, and contracted Betty Comden and Adolph Green to rewrite the book with much of Leonard Bernstein's original score discarded. The film features only four songs from the original musical, those composed by Leonard Bernstein, and six that were created especially for the screen.
During the dockside scenes that open and close the movie, the three sailors' ship, seen in the background, is the USS Nicholson (DD 442), a Benson/Gleaves-class U.S. navy destroyer that was commissioned in 1941 and saw action in World War II and the Korean War. The Nicholson was eventually sold to the Italian navy, which used it for target practice, sinking it in 1975.
The only musical numbers retained from the original musical were "New York, New York", "Come Up To My Place", "Miss Turnstiles" and "A Day In New York". Roger Edens composed six new songs for the film to replace the following songs: "I Can Cook, Too", "Some Other Time", "Lucky To Be Me", "Lonely Town", "Carried Away", "I Understand", "Carnegie Hall (Do-Do-Re-Do)", "So Long Baby", "I'm Blue" and "Ya Got Me".
The crew tried to keep the location filming in New York City as low-key as possible. Many of the scenes were filmed from the back of a station wagon. At the end of "New York, New York", as the camera tilts up at Rockefeller Plaza, you can see the skating rink lined with spectators watching Frank Sinatra and Gene Kelly.
The movie was based on the stage musical of the Jerome Robbins ballet entitled Fancy Free, which opened at the Ballet Theatre in New York in the spring of 1944. In addition to writing the book for the stage version of On the Town (1949) and writing the screenplay for the film, Betty Comden and Adolph Green appeared in the stage version in the roles of "Claire" and "Ozzie."
One of the promotional tag lines for the film was "Twice as gay as "Anchors Aweigh"!". "Anchors Aweigh" was a 1945 musical that also starred Gene Kelly and Frank Sinatra as sailors. Since it was criticized for being dull, "On The Town" was marketed as being "Twice as gay as "Anchors Aweigh"!"