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How others will see it. This movie is aimed at a teen and twenty-something audience, despite a boomer rock soundtrack. Yes, it's only a comedy, but parents (and other adults) might grimace when Sandler assaults a hockey scout and a tax collector within the film's first reel.
You'll see the plot turns a mile away. A hottie tour publicity agent? Could be a girlfriend for Sandler. He needs to raise money to buy grandma's oversized house. Could happen. Carl Weathers wants to become Sandler's coach. It's a possibility.
How I felt about it. There are some funny moments among all the groaners, including a middle-aged Asian sleepover, a truck driving over a wooden hand, and ... well, if I watched the entire movie over again, I might find another one. Meanwhile, Bowen says less and wears less as the film progesses. By the end of the movie, she's mostly just a smiling cheerleader for the Sandler cause. And let's face it, Sandler is certain to get the best of his tour rival, sooner or later.
The film's premise is that we should root for Sandler, the working man's hero (not that he has a real job), despite his tendency to assault people, and his waste of natural talent (namely, an ability to hit things hard). Since Sandler is a dubious protaganist, we need further motivation. This is provided by making his toughest competitor, McDonald, into an enormous jerk, and transforming a mercenary goal (winning golf tournaments) into a charity drive (a mansion for granny).
The manipulation is on the level of a children's cartoon, which also explains its appeal. If you are looking for a film that tells you how you should feel with every consecutive shot, Happy Gilmore is for you. No thinking is required.
But isn't it great that a bad sport, Shooter McGavin, gets what's coming to him? Doesn't that set an example of why one should compete fairly? The problem with this argument is that the poster child for bad sportsmanship is as much Gilmore as it is McGavin. It would be better if the tour trophy went to a guy who is as nice while competing as when he's not. Regardless of whether such behavior is cinematic.