Worst Picture Winners: Jack and Jill


When it comes to review and analysis for the sake of education, sometimes the best movies to review are the ones that fail on such a catastrophic level that they become a perfect example of what not to do when creating a movie. Because of this, I’ve decided to do a series of reviews that look specifically, in no particular order, at movies that have claimed the Golden Raspberry Award for worst picture of the year, and examine precisely how they earned such an award.

So what film that claimed the worst picture razzie is first on the list? Well, I decided to dive in at the deep end, and watch the movie that literally won all the razzies that year: Jack and Jill.

Jack and Jill is one of many critically panned comedy movies made by Happy Madison Productions. The fact that it’s considered one of the absolute worst of the bunch, is saying a lot, given that, since 1999 they have produced a grand total of two movies to have earned a “fresh” ranking on Rotten Tomatoes.

Jack and Jill tells the story of twin siblings Jack and Jill Sadelstein, both of which are portrayed by Adam Sandler, despite the fact that opposite sex identical twins are virtually non existent (and yes, the film on several occasions confirms to us that Jill has a vagina, in case we were thinking otherwise). But I’m not going to attack this film for it’s failure in biology, I’m here to criticise it’s failure in comedy.

Surprisingly enough, this movie’s main style of comedy isn’t slapstick or toilet humour (though we see a fair bit of both). Instead, we get to experience some cringe comedy. Or, at least what Adam Sandler thinks passes for cringe comedy.

Cringe comedy usually works in situations that have some realism to them, and also in situations where the character the comedy is focused on suffers due to their own stupid actions. We get none of this here. Take the scene at the Thanksgiving dinner table. Jill is an over the top cartoonish character who is consistently rude to the other guests. Yet despite this, Jack’s wife Erin seems to show her respect, and wants her to be there with the family, apparently oblivious to how awkward and rude she is with people. The suffering that usually comes with cringe comedy is barely featured either. Jill never rarely shows regret for anything she says, while Jack mostly looks too bored to be suffering at all.

On top of a lack of comedy, the characters themselves are neither endearing nor likeable. Jill is simply following the formula of “man dressed as woman=funny, weird voice=funny, strange awkward behaviour=funny”. Jack’s annoyance with his sister is perfectly understandable, but it seems that not only is Sandler giving a tired, half arsed performance, but he proves to be a jerk more than willing to take full advantage of his sister simply to further his career. Neither of these characters have enough positive traits to be endearing, nor funny lines to be at least entertaining.

Then that brings us to the plot, or at least, the story line that pulls the awkward string of unfunny scenes together while not really being the main focus of the movie


The main focus being “haha Jill is awkward”.

Jack works in advertising, and needs to get Al Pacino to star in a Dunkin’ Donuts commercial or else he’ll lose all connections with the company. And as soon as Al Pacno lays eyes on Jill, he decides he wants to date her. A lack of hilarity ensues.

If I can give this film any credit, it’s that Al Pacino going after Jill actually has some reasoning behind it. Assuming literally no one is going to care about me spoiling the ending, it turns out Al Pacino is auditioning for Man of La Mancha. Being very much a method actor, it turns out Pacino has simply been trying to imitate Don Quixote, by finding some woman, pretending she’s something she’s not, and pursuing her to no end despite having only just met her.

There are, however, two problems with this. The first is of course the question why Sandler believed anyone who would go to watch a movie like Jack and Jill would have any knowledge of Man of La Mancha. The second is just how weird and creepy Pacino acts while pursuing Jill, refusing to take no for an answer, and getting weirdly physical. If Jill didn’t literally have the strength of a bodybuilder, then let’s just say I would have been very worried for her safety.


This scene is a lot more awkward than it looks

To be quite honest, I went into this movie expecting offensive, childish, ridiculous trash, but what I actually found didn’t go that far. This movie is not outrageous, it’s pathetic. It’s humour is so unfunny that when it’s not doing the obvious like fart jokes, cross dressing jokes and a Mexican guy making illegal immigration jokes,  I’m genuinely not sure what I’m supposed to be laughing at (y’know, aside from the fact that a man dressed as a woman is supposedly comedy gold by default).

In all honesty, the funniest part of the movie is funny for entirely the wrong reasons: after finally completing Jack’s Dunkin’ Donuts commercial, Pacino’s reaction is to burn it, and ensure no one ever finds out about it. I thoroughly believe it is impossible to watch this scene without believing that Pacino is, in fact, talking about Jack and Jill



Awfullness ranking


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