Happy Gilmore Then and Now Cast: Then and Now

Inside this ranking: 15 headline-making yachts, following the source's published order and reported estimates. Prices can change and should be read as editorial estimates rather than live appraisals.

• Adam Sandler — Happy Gilmore — Adam Sandler — Happy Gilmore. Sandler co-wrote and starred as the hockey-minded golfer in 1996, then returned nearly three decades later for Happy Gilmore 2.
• Christopher McDonald — Shooter McGavin — Christopher McDonald — Shooter McGavin. McDonald played the polished rival Shooter in the original and returned for the 2025 sequel.
• Julie Bowen — Virginia Venit — Julie Bowen — Virginia Venit. Bowen portrayed tour publicist Virginia in 1996 and reprised the character in Happy Gilmore 2.
• Carl Weathers — Chubbs Peterson — Carl Weathers — Chubbs Peterson. Weathers played mentor Chubbs, translating Happy's hockey power into golf technique.

Tap any name above to jump in, or start at entry #40 and count down to number one.