Jim Carrey made more per film at his peak—he was the first actor to command $20 million for a single role—but Adam Sandler figured out the streaming game before anyone else. While Carrey was still negotiating studio deals in the 2000s-2010s, Sandler locked in a $350 million Netflix contract that essentially prints money regardless of critical reception. That one deal alone represents 83% of his total net worth, whereas Carrey's fortune is spread across decades of theatrical releases with no comparable mega-deal.

The career trajectories reveal different risk profiles. Carrey pursued prestige alongside paychecks—he took dramatic roles in 'The Truman Show' and 'Eternal Sunshine of the Spotless Mind' that didn't maximize earnings but enhanced his reputation. Sandler doubled down on his formula, recognizing that Netflix values consistency and audience loyalty over Rotten Tomatoes scores. Streaming fundamentally rewards volume and reliability differently than theatrical distribution, and Sandler capitalized on that shift while Carrey's peak earning years were behind him.

There's also the compounding effect of timing and reinvestment. Carrey's modest living likely means lower returns on capital—he wasn't aggressively building business empires or leverage deals. Sandler, meanwhile, has production company deals, backend points on multiple projects, and the kind of portfolio approach that turns $420M into a compound-growth machine. Carrey earned more total dollars across his career but structured his wealth in a way that generates less ongoing passive income, while Sandler built recurring revenue streams that keep multiplying.