Keaton was the higher earner on paper, commanding premium salaries during silent cinema's golden age, but he was a hired gun for studios that owned his films outright. He worked under contract for major studios who controlled distribution, licensing, and long-term revenue streams—meaning his peak $200M annual equivalent evaporated the moment the paycheck cleared. Chaplin, by contrast, founded United Artists in 1919 specifically to retain ownership of his work. This wasn't just ego; it was structural. While Keaton's films were generating massive revenues that flowed to studios, Chaplin's catalog generated recurring income he actually kept. The difference between being paid to perform versus owning what you create is the difference between a salary and a business.

Keaton's financial collapse came from compounding bad decisions that Chaplin simply never made. Keaton lost control of his career, suffered alcoholism that studios exploited, and was systematically marginalized as talkies emerged—he became unemployable exactly when his leverage disappeared. Chaplin, meanwhile, remained the sole decision-maker on every project. He could choose which films to make, when to pivot from silents to talkies, and how to market himself. 'The Great Dictator' worked because Chaplin bet on himself at 50 years old when most actors were fading. He earned $7.5M from a single film and kept the upside, not a studio's finance department.

The real story isn't that Chaplin out-earned Keaton—it's that Keaton optimized for short-term salary while Chaplin optimized for long-term ownership. Keaton made more per year but had zero residual assets; Chaplin made less per year but built a self-perpetuating asset. By age 88, Chaplin was still collecting checks from decades-old films. Keaton was dead and broke at 70, his genius treated as a disposable commodity. This is why modern creators obsess over ownership: Keaton proved that even unparalleled talent becomes worthless without it.