After filming repeated takes of the scene where Sky (Marlon Brando) and Nathan (Frank Sinatra) first meet, they had to quit for the day when Sinatra had eaten too much cheesecake. He said he could not take one more bite. Brando, knowing how much Sinatra hated cheesecake, had purposely flubbed each take so that Sinatra would have to eat piece after piece of cheesecake. The next day, they came back and shot the scene perfectly on the first take.
Frank Sinatra loathed the non-singing Marlon Brando for getting the starring role, while Sinatra got a lesser part. His nickname for the sometimes barely comprehensible Brando was "Mumbles."
Gene Kelly was sought for the role of Sky Masterson, but MGM refused to loan Kelly to Samuel Goldwyn. Kelly had been so eager to play the part that he never forgave MGM for this, later stating "I was born to play Sky Masterson like Clark Gable was born to play Rhett Butler."
Marlon Brando had been cast in the role of Sky Masterson, a role coveted by Frank Sinatra, while Sinatra was relegated to the supporting role of Nathan Detroit. Relations between the two actors were strained during production. Many years later, Brando said of Sinatra, "Frank's the kind of guy who, when he gets to Heaven, is going to give God a hard time for making him bald."
The decision to cast Marlon Brando was hotly contested, largely by Frank Sinatra, who wanted the part of Sky Masterson himself. Later in his career, he made Sky's big number, "Luck Be A Lady," part of his stage act.