Happy Gilmore

Adam Sandler as a failed hockey player with a 400-yard running drive and a grandmother in trouble with the IRS — somehow this became a 1996 classic. Christopher McDonald's smug Shooter McGavin, Carl Weathers' one-handed mentor Chubbs, and a Bob Barker brawl that won MTV's Best Fight. You've attempted the Happy Gilmore swing at least once.

Happy Gilmore, released February 16, 1996 and directed by Dennis Dugan, arrived as Adam Sandler's follow-up to Billy Madison. The premise was gloriously absurd: Happy is a failed hockey player whose slapshot turns out to be a 400-yard running golf drive, so he joins the tour to save his grandmother's house from an IRS seizure over $270,000 in back taxes. The supporting cast crystallized the 90s comedy formula — Christopher McDonald's Shooter McGavin as one of the decade's most satisfyingly smug villains, Carl Weathers as one-handed mentor Chubbs Peterson (an alligator took the hand), and Julie Bowen as tour PR director Virginia Venit.

The film made its cultural imprint immediately. The Bob Barker caddy brawl — the beloved Price Is Right host coolly beating Happy senseless on the fairway — won the 1996 MTV Movie Award for Best Fight and remains one of the great celebrity cameos of the decade. Made for $12 million, the film took in $41.4 million worldwide; critics were split (Roger Ebert gave it 1.5 stars), but audiences never let it go.

Its staying power has been unusual for a 90s sports comedy. The running-start swing became a permanent piece of golf culture — real tour pros still break it out for fun — and the one-liners never left circulation. A sequel, Happy Gilmore 2, finally arrived on Netflix in July 2025, dedicated to Morris the alligator from the original.

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