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After making his fortune on and off Wall Street, Joe was one of the first Eastern businessmen to grasp the potential of the movie business. By the mid-1920s, the American film industry was turning out 800 films a year and employed as many people as the auto industry. This was "a gold mine", Joe told several friends. After buying a chain of thirty-one small movie houses, Joe realized that the way to make real money was on the production side. Moreover, he was attracted to the glamour of Hollywood. Not only could he influence the way films were made, he could meet dazzling young women.

Gloria Swanson

- While his wife Rose was in Boston, pregnant with their eighth child, Joe was in Hollywood engaged in his notorious liaison with the superstar Gloria Swanson.
- Swanson was by no means Joe's first extramarital adventure, but she was his first real affair. She was the perfect trophy to symbolize the great worldly success he had achieved.

- Joe Kennedy had become so entranced by Gloria Swanson and Hollywood that when his father PJ Kennedy died in May of 1929, Joe would not leave California to attend the funeral. Joe's cousin Joseph Kane later confronted him saying, "You son of a bitch, you didn't even go to your father's funeral. You were too busy on the West Coast chasing Gloria Swanson around."

A friend, Kane Simonian, observed, "Joe Kennedy didn't attend his father's funeral....When someone doesn't go to his father's funeral, you can believe he would do anything."