Billy Madison (1995)

The movie is the person, juvenile and silly in both tasteful (yum, glue!) and distasteful ways (yuck, masturbation porta-potty!), showing glimpses of genuine sweetness (“Everyone my age pees their pants. It’s the coolest!”) amidst the sloppy-like-Joes coming-of-age arc, and in the end getting a passing grade (but barely), thanks to consistent pops of good, goofy comedy (see the musical number; the O’Doyles’ fate) and one-liners galore (“You get your ass out there and you find that fucking dog”).
5

Punch-Drunk Love (2002)

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A psychologically troubled novelty supplier is nudged towards a romance with an English woman, all the while being extorted by a phone-sex line run by a crooked mattress salesman, and purchasing stunning amounts of pudding. (IMDb)
Delightfully bizarre-within-the-mundane (our lead has seven sisters and sells novelty plungers in a big storage locker) and artfully and purposefully constructed (the loud and constant soundtrack, sudden sounds, tracking shots, zooms all envelope us in Barry’s anxiety; the colour flares are a cool touch too). It’s a well-acted character study of a man just trying to cope in this overwhelming world, and the solace and redemption he finds strike all the right chords after so much dissonance.
8.5/10 (Amazing)

 

The Waterboy (1998)

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A waterboy for a college football team discovers he has a unique tackling ability and becomes a member of the team. (IMDb)
Mostly just really juvenile and unfunny, from Sandler’s annoying schtick (though his extravagant water obsession as a “water distribution engineer” brought lots of laughs) to the childish “bayou bumpkin” stereotypes to the eye-rolling talking heads gag. The sports storyline is also completely predictable, of course, though the requisite climactic game is admittedly done quite well, from the halftime turnaround (“Remember the time Bobby Boucher showed up at halftime?”) to the goofy announcers.
5.5/10 (Poor)

 

The Meyerowitz Stories (New and Selected) (2017)

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An estranged family gathers together in New York for an event celebrating the artistic work of their father. (IMDb)
Shifts from a first act packed to the brim with quirky, rapid-fire dialogue (Hoffman’s self-absorbed Harold is the highlight here: “It’s my protest”), entertainingly edited (see the snippets montage) to a downright hilarious second act (see the siblings’ note taking, Pam obsession) and a slower, more ponderous third act that really brought out the complex dynamic between the brothers and The Dad (both Stiller and Sandler are great–see their pre-fight exchange). Well-paced, and never predictable.
7.5/10 (Really Good)

 

Blended (2014)

After a bad blind date, a man and woman find themselves stuck together at a resort for families, where their attraction grows as their respective kids benefit from the burgeoning relationship. (IMDb)
An awfully predictable screenplay here is especially cringe-worthy in its first act as cheap and unfunny humour attempts to grab your attention, painfully wooden dialogue establishes the main characters, and simple plot points set up the storyline in seconds. Yet the film becomes tolerable and even engaging as it progresses; the humour grows on you, and the contrived emotional peaks are undoubtedly effective, for as caricatured as the characters are, you do end up caring for them.
6/10 (Mediocre)

Happy Gilmore (1996)

A rejected hockey player puts his skills to the golf course to save his grandmother’s house. (IMDb)
Sandler is a riot here as the ironically-named title character, whose anger management issues and general vulgarity hilariously contrasts with the pristine and classy world of professional golf that he enters into. The plot is fairly basic, but the memorable protagonist, along with an excellent antagonist and a healthy smattering of quirky secondary characters and outrageous humour (see the Bob Barker brawl) transforms the cliche sports underdog story into an instantly classic sports comedy.
7/10 (Good)