In the novel, Jim Hawkins is a teenager. However, Jackie Cooper was just turning thirteen at the time, and he struggled to play the part as “older” and “mature." He said, “It was the first time anyone had made me think about what I was doing, really to consider my character and how to make him come alive.”

Director Victor Fleming (known for his work on The Wizard of Oz and Gone with the Wind) imagined the adventure tale as a dynamic color picture. Unfortunately, Louis B. Mayer, the studio head at MGM, nixed the idea. A limited budget also meant that rather than finding a real ship for the pirates, they instead converted a yacht for filming.

Cooper and Wallace Beery worked together in four films, but the elder actor had a way of rubbing people the wrong way. For instance, when making The Champ, he told Cooper that their co-star, George Raft, known for gangster roles, had actually killed people. Raft didn’t particularly like the fib. According to Cooper, Beery would sometimes “steal the scene” by scratching his head or flubbing lines – a method used to throw off another actor’s moment in the spotlight.

Cooper was excited to use the prop guns in the film and convinced the special effects crew to let him test one out before his big scene. Unfortunately, the flash powder landed on Beery’s foot. To make matters worse, it was the foot that was strapped behind him to make it appear as if he only had one leg. “He yelled bloody murder. I have since been attacked by flash powder myself, and I can testify that it is no more painful than being run into by a lit cigar,” Cooper said.

Louis B. Mayer wasn’t happy with the film’s ending. Despite following the book’s plot, he disliked the unhappy ending and that Jackie Cooper didn’t have his typical crying scene – something he felt audiences wanted. So despite the production already lasting three months, everyone was called back for reshoots. Beery was especially displeased with returning to work and would stall in scenes or retreat to his dressing room for long periods of time.