Jim Carrey

Carrey's wealth story is the perfect case study of 1990s comedy stardom converted into generational wealth. His legendary salary escalation from $350,000 for 'Ace Ventura' to $20 million for 'The Cable Guy' in just two years remains one of Hollywood's most dramatic pay bumps. The key wasn't just the upfront money—Carrey negotiated backend deals on hits like 'Liar Liar' and 'Bruce Almighty' that paid him percentage points of profits, turning $150+ million grossers into personal windfalls of $25-35 million per film.

What sets Carrey apart from other '90s stars is his investment discipline. While peers bought sports teams or launched vanity projects, Carrey quietly built a diversified portfolio heavy on blue-chip stocks and California real estate. His Brentwood compound, purchased for $3.8 million in 1994, is now worth over $20 million. He's been selling off properties strategically, including a $13.4 million Malibu ranch sale in 2013, suggesting active wealth management rather than lifestyle inflation.

The wildcard in Carrey's portfolio is his art career—not a celebrity hobby, but a legitimate revenue stream. His paintings and sculptures sell for $10,000-$75,000 each, and he's moved over 200 pieces since 2011. Combined with his decision to be highly selective about roles (turning down countless sequels), Carrey has maintained his mystique while letting compound interest work its magic. At 61, he's positioned more like a tech executive than a traditional Hollywood star: wealthy, private, and focused on creative fulfillment over maximum earnings.