If you were ever a Sandler fan back in the day, the coin flip tended to be between 'Billy Madison' and this for his best movie - the coin ultimately landing on this most of the time. The humor involved is a little less goofy than 'Billy Madison', leaning a little more on sarcasm, but still keeping enough of that randomized humor we've come to love so much with Sandler films (at least the older stuff). Though I do tend to lean towards 'Madison' a bit more, it makes more sense to recommend this one to the masses for what it is.
Happy Gilmore (Sandler) is an aspiring hockey player, and though he's not entirely good on the ice, he has an insanely strong slapshot. We learn through the intro that since his Dad passed away, he became a bit of a trouble-maker with a short fuse, and he holds the record for the only skater in the league to take off his skate and try to stab someone with it. But there is balance in his life, as his kindly, loving grandmother (Frances Bay) shows us his soft side, as he'd do anything for her. That "anything" now involves paying the IRS a lot of back taxes that she owes, or else her house gets repossessed.
During a bet with two of the repo men, Happy learns that he can makes some cash hustling people at the driving range when he smacks a golf ball an incredible distance. This eventually leads him to Chubbs (Carl Weathers); a former golf pro who sees Happy's skill, and takes him under his wing to play professional golf. Happy denies him at first, but when it comes to getting back his grandmother's house, he listens to the sound of the potential money he could make on tour. Here, he meets golf favorite, Shooter McGavin (Christopher McDonald) who quickly becomes his nemesis, disapproving of Happy's style, and claiming him as pretty much an insult to the game (like a punk rocker at a ballet).
Public relations head Virginia Venit (Julie Bowen) on the other hand is very impressed by Happy's long drive and overall skill, and implores Tour Commissioner Doug Thompson (Dennis Dugan) to allow him to stay on, but while watching his outbursts, and trying to keep them under control. It's relatively predictable how it all goes, but it can't be denied that the execution of it all is hilarious, and it fits very well as a blend of the sports movie craze of the 90s, as well as the Sandler craze of the 90s. It would all eventually come around again with 'The Waterboy', but that's a review for a couple of weeks from now.
A few more things that make this one a bit more memorable for people include some celebrity cameos, not the least of which is former 'Price is Right' host, the late Bob Barker - who gets in a fist fight with Happy, providing us with a pretty funny and unexpected fight. But also on board are the late Richard Kiel as Happy's former boss. He'd be most recognized as Jaws in the 'Bond' film 'Moonraker', but he was also the voice of Vlad in 'Tangled'. Let's also not leave out a fellow Canadian, Joe Flaherty, as "Jeering Fan" (or as I like to refer to him as, the "Jackass" guy) or Ben Stiller as a nursing home orderly with a short fuse. 'Billy Madison' didn't have much of that, unless you count Chris Farley as the bus driver, but even that's really just an SNL attachment.
I'm not entirely sure what else can be said about 'Happy Gilmore', sadly. It's a great way to see Sandler in his prime, and it's great that the comedic formula does a sort of shift from 'Madison' to 'Gilmore', showing us a decent range for him right off the bat. I'd say that if you wanted to see a more stereotypical goofy Sandler, 'Billy Madison' is the one to watch, but if you prefer his comedy through anger and sarcasm, this is the one to lean towards. Otherwise, on the surface, it's really just another underdog sports movie with a bit of a twist. But still, it yields hilarious results, and a lot of the comedy in this isn't even from Sander as opposed to the dry and seemingly accidental deliveries from Christopher McDonald.
So definitely check it out if you are a little curious about Adam Sandler's early work. Hell, back-to-back 'Billy Madison' and 'Happy Gilmore' just to say that you've seen the films that lead to Sandler's production company, 'Happy Madison Productions'. Let's face it, that's a company with more misses than hits, but there are a few titles under their belt that I can say I still enjoy. If it weren't for these movies bringing Sandler into the spotlight as almost a direct competition to Jim Carrey, who knows what could have happened to the randomized comedy I've grown to enjoy so much from Adam Sandler - unless we're talking about 'Zohan'... dammit, that was just too random.