Twenty years ago, when asked what the best golf movie was, most moviegoers would have answered Caddyshack. But a while generation of kids unfamiliar with the names “Rodney Dangerfield” and “Bill Murray” would know answer that question with: Happy Gilmore.
To be up-front: I love this movie. But it's a bad movie. However, its initial idea isn't terrible. In addition to a fish-out-of-water, it's about a man who's persistently angry, both lashing out at and fueling his rage towards his physical outlets. However, the character ends up as merely the first incarnation of The Adam Sandler Character that he's been recycling in movies (many of which were also helmed by Dennis Dugan).
Happy Gilmore is as mentioned, an angry man. Gilmore is in a constant state of frustration because of his desire to play hockey, but his disproportional placements of effort/interest and talent. Eventually, he applies himself to golf for a contrived reason, and gradually finds success, with intermittent outbursts of his temper. It's these outbursts that were the biggest problem in Dugan's Happy Gilmore: this Happy Gilmore is—to quote Roger Ebert—a violent sociopath. What's worse is that the movie approves of his senseless violence and misconduct.
In the reincarnation, Happy would be no less angry or frustrated, but his actions would have more serious consequences. Instead of this lovable, uppity angry man, we'd get a cynical, jaded, and more inwardly-furious man; we both come to expect, and fear his outbursts. This Happy Gilmore isn't a glib retelling about a jerk who gets everything because he “believes in himself,” but rather it's about a man who hates what he has to do for a living.
Where the humor in the new Happy Gilmore would be much like they are in the original: the rubbing up between the real, disapproving world and with Gilmore's willfulness. This requires a re-emphasis on how he gets angry, and how he responds to it; when Happy first plays in a (semi-) professional golf context would show the limits to the man's anger on the golf course. It's what would really happen when you have this violent sociopath on a golf course whose predilection towards violence is informed by another sport (a concrete example might be O.J. Simpson). The movie would still be able to keep its great visual gags, such as the shots from the ball's point of view, or the discussion between Virginia and Doug Thompson in between Gilmore's censored cursing, without significantly tweaking the reasons behind them.
While it'd be a tougher part, Sandler could still work for the more inward Happy Gilmore. Punch Drunk Love illustrated that Sandler's private nature is a stronger screen presence than when's flamboyantly acting out, but the new Gilmore would be both. And much of this would be challenged by the two people of Julie Bowen's (more attractive, pre-nosejob) Virginia and Carl Weathers' Chubbs Peterson. Because of Bowen's strength as an actress, Virginia already has more dimension than the original screenplay really gave her, but a stronger character would be for her to be more career-focused and less interested in Happy for himself, but rather to be romantically playing him so she can use him for her own career advancement.
And instead of Carl Weathers as a sort of Magical Negro (aside: much as I dislike Spike Lee, this is a magnificent phrase he has here). Instead, Chubbs is a nice man with a great sense, but ultimately a has-been. A talented, smart has-been who's watched the only world he ever loved pass him by. Whether or not he should die is a different matter. His death has no real consequences (and happens for a contrived, unfunny reason), but in a sense it might make some thematic sense: He dies just before Happy becomes a success i.e. Chubbs can't even be close to the top of golf through proxy.... But then again, there's also something inherently uplifting in having someone finally get that which they've spent years searching for themselves—to do that specifically might require Chubbs to be more of a “traveling golfer” (without his becoming Baggar Vance, another Magical Negro), than a club pro.
Shooter McGavin would require recasting. McGavin is a spoiled, entitled golf snob who feels threatened by Gilmore because he covets his talent. However, in the original, nothing is done with the character despite the inherent irony that McGavin resents Gilmore for what he has, but never worked for, when McGavin himself has obviously never had to work for anything. McGavin has to have more of an implicit arrogance to himself—exude that entitlement from his presence. Someone like John Malkovich would be a better fit than the more boisterous, un-Connecticut-like presence of Christopher McDonald.
The other major, non-Gilmore source of funny in the movie is Ben Stiller's Orderly. While essentially a cartoon, he can still work, but to fit with the more realistic-sardonic tone of the film, he'd have to be more evil. Not evil evil, but funny evil. Without being too cliché, the character he'd most nearly resemble is Heath Ledger's Joker: wry almost to a fault, but too funny for the audience to be able to clearly see the prescient menace that he is to the elderly people. (Plus, keeping him unrealistic still allows for the great “Check out the name tag. You're in my world now, grandma.”)
The only character who would have to be totally dropped (requiring a major structural revision) would be the jerk (Joe Flaherty's “Jeering Fan”) who Shooter McGavin hires to bug Happy into incriminating himself. “You Dumbass!” doesn't fit with a more serious, comically dark Happy Gilmore, the reason primarily being: it's not funny. The character isn't funny. And at that, he wouldn't be tolerated in the golfing world anyway (wealthy people can always afford to remove those they don't like).
However, this character's excision has the deeper structural implications as he's more or less what's the force against which Happy is forced to overcome in the second and third acts. But while the actually scripted character doesn't work, the idea is natural and strong. Shooter would pay someone to sabotage Gilmore, but it shouldn't be someone to resorts to yelling, but making Happy act up in other ways: slipping some laxative in his drinks, and then sending him a note “time to go!” as an example. There are any number of progressively escalating things that this character could do to Gilmore that get him kicked off the tour, but it would have to culminate in something far more fiendish than hitting him with a car. Specifically, McGavin should use this individual to illustrate to Virginia that Happy's worth more to her and her career as a freak than as a golfer.
The Subway ad could be more than just a supplement to Grandma's house payment, but could be Virginia's realization that she can exploit Happy as a personal breadwinner. Circumstance in the movie would indicate that everybody would win: Happy gets enough money for Grandma, Virginia gets this new publicist's contract, McGavin gets rid of Gilmore, and everybody wins. In short: everything (including Happy) should be telling Happy that he's not a golfer. He has to realize that it's his odd God's gift of talent, and the sui generis energy and style that makes him a golfer (indeed, celebrity almost).
