Punch-Drunk Love (2002)
P.T. Anderson takes everything you'd expect from an Adam Sandler flick-a lovable meathead prone to violent outbursts, a disastrous attempt at phone sex and a subplot revolving around $3,000 worth of pudding-and runs it through the Creepy Indie Film filter to make something nobody thought possible: the Thinking Man's Adam Sandler Movie.
Verdict: It's slow going at the start, but once you get through the first hour, it suddenly becomes the single best role of Sandler's career. Between a scene where he explains a scheme involving pudding fraud to Luis Guzman and an amazing face-off with Philip Seymour Hoffman, the payoff's totally worth it.
Cracked Fact: This movie is 97 minutes long. 63 of those are spent in extremely uncomfortable pauses.
ALSO CLASSICS: Billy Madison, The Wedding Singer
Underrated The Waterboy (1998)
The most quotable Sandler flick on the shelves (as evidenced by a dozen movies where Rob Schneider shows up to remind someone that they, too, "can do it!"), this one takes his obsession with sports movies and combines it with his love of playing profoundly stupid characters, and ends up with one of the best low-brow comedies of the '90s.
Verdict: Okay, it doesn't actually have much of a "plot", and character development takes a back seat to funny voices and sight gags-but when you've got a movie that pits the Fonz against Snowman from Smoky and the Bandit in a battle of slapstick football, that's all the plot you really need.
Cracked Fact: Hands down the funniest movie of Fairuza Balk's career. We're ignoring The Craft, since Waterboy was supposed to be funny.
Verdict: Despite the fact that it's based around a pretty depressing premise that only gets weirder in the final scenes, 50's got a lot of heart to it. Plus, Sean Astin's shameless overacting as a steroid-popping homosexual is worth the price of a rental alone.
Cracked Fact: If you're making a movie and you find yourself pointing a camera at Rob Schneider for more than, say, two scenes of it, you should probably stop. And by probably, we mean immediately. ALSO UNDERRATED: Big Daddy, Airheads
Overrated Mr. Deeds (2002)
And now, an inside look at how Hollywood works:
"Say Chet, who should we get for the Gary Cooper role in our remake of Mr. Deeds Goes to Town?"
"Well, Brad, how about that guy who played Canteen Boy?"
Verdict: It's hard to criticize a remake of a sixty year-old Frank Capra movie for a lack of originality, but this entire flick watches like it's made of scenes left over from every other Sandler movie. Scenes that were cut for a very good reason.
Cracked Fact: Even though both movies feature Steve Buscemi and John Turturro, Mr. Deeds is roughly 18,000% less funny than The Big Lebowski.
Verdict: Sandler's at the center of some genuinely funny scenes in this one-his argument with Flor while her daughter translates is a highlight-but the whole thing drags along mercilessly and indulges in way too many romantic comedy clichés to really go anywhere with its jokes.
Cracked Fact: There's a scene in Spanglish where Sandler's character refers to Paz Vega as being "drop-dead crazy gorgeous." That is one hundred percent true. ALSO OVERRATED: The Longest Yard, Bulletproof
Total Crap Click (2006)
In this movie, Sandler finds a remote control that lets him to skip the most monotonous and painful moments of his life. Assuming you're watching Click on DVD, you've got one too.
Verdict: When this thing came out, it was hard to find a review that didn't make a joke about the film not "clicking" with the audience. That's because it was too busy "sucking ass."
Cracked Fact: There was a time when Adam Sandler and Christopher Walken would've meant box office gold. That time? 1998.
Little Nicky (2000)
If you've ever wondered why so many people hate Adam Sandler, look no further than this cinematic atrocity. With an annoying "funny" voice and face, phenomenally lame jokes that only get a reaction from other characters in the movie, extended sequences showcasing Sandler's basketball skills, and-of course-a tacked-on moral about Just Being Yourself, it's not just Sandler's worst. It might be the worst movie of any SNL cast member.
Verdict: It's hard to say that watching a movie is worse than contracting, say, leprosy, but Since Nicky opens with Jon Lovitz getting raped by a man in a bird costume and just goes downhill from there, traditional measures of quality don't really apply.
Cracked Fact: Although it wasn't widely publicized, Sandler was actually brought to trial at The Hague for war crimes after releasing this piece of crap, and only escaped hanging after promising to do a P.T. Anderson film.
ALSO TOTAL CRAP: Eight Crazy Nights, Anger Management