Adam Sandler's 'Jack and Jill' is As Awful As You Expected

Sometimes a movie will come along that irks you, causes the veins on your head to pop out with frustration to such an extent that you don't even want to mull it over for days before blasting it with an angry retort. I'd like to take a moment and congratulate Adam Sandler and Dennis Dugan, an actor/director combo that usually brings out this kind of ire but never like this. Never like this. The movie is Jack and Jill. The premise is ridiculous. Sandler plays both Jack Sadelstein, family man and ad exec living in L.A. with his wife—a characterless mannequin that looks an awful lot like Katie Holmes—and two children, and Jill, Jack's annoying, noxious, abhorrent sister who comes to her brother's house for Thanksgiving.
Oh and did I mention ugly? Jill is ugly, too, and not just in a physical sense. That would just show an ignorance and cruelty extended forth only by someone in a movie like... well, Jack and Jill. Jill's soul is ugly, and though she says she just wants love from her family, she proves with every fiber in her makeup that she isn't willing to be understanding of their needs.
But that's not the message Dugan and Sandler want to convey here. Judging from Jack and Jill, they believe you should love someone no matter how intrinsically unappealing they may be. Maybe that's the message Dugan actually wants people to take from watching in his movies, works that have no sense of structure, style, or cohesion. Literal scenes seem chopped from Jack and Jill, moments that might reveal some sense of clarity as to character actions or even reactions, but probably not. The same goes for Sandler and his idea of comedy, the kind that seems satisfied with prat falls and fart gags. Seriously, when was the last time you laughed at a fart gag?
Those aren't even the crux of the comedy in Jack and Jill. The term one-joke movie gets bandied about like a rubber ball tied to a paddle, but Jack and Jill seems happy with cutting that string so the ball can bounce around the room hitting everyone in the audience right between the eyes. Jill is a woman. Jill is played by Sandler dressed as a woman. Jill is supposed to be unattractive, manly some might call her. Everyone in the world of this film realizes this. Cue "witty" line about said set-up and yuck yuck yuck about it for 90 minutes. It's a joke that's hateful in its very essence, but that doesn't seem to occur to Sandler, who seems to enjoy playing both straight man and funny woman here.
All the while Jack and Jill plays like one, big, inside joke between Sandler and others on set, most of them Hollywood notables offering their appearance to be shown in the movie. Chief among them is Al Pacino playing himself, who coincidentally is both being hunted by Jack for a new Dunkin' Donuts ad and falling head over heals in love with Jill. Pacino plays himself with a lunatic's mask attached. He seems to embrace the "full Pacino" he's been playing recently and doesn't mind mocking himself. That aspect to Jack and Jill might not be as hateful or as annoying as the rest of the movie, but it's certainly not funny.
But that isn't even where Jack and Jill's ability to pull in A-list stars reaches it chilling pinnacle. Left and right you'll notice familiar faces, some playing themselves, others playing ludicrous characters. It's nice seeing Dana Carvey show up in a film after a nine-year absence, but good luck recognizing him. However, it's a certain A-list superstar who makes a brief appearance that will have you disregarding everything he's saying as you scream "WHY" at the screen. Of course, we know why, as Sandler's pull in Hollywood seems to be expanding ever greater with each passing trash heap he headlines.
That might be where this anger comes from. It's one thing for awful comedies like Jack and Jill to be made independently, by people who will probably never make it in the industry and will simply slink into obscurity before their "works of art" are even introduced to daylight. You don't even have to pay them any attention unless you feel some masochistic tendencies coming on. It's another for something this insulting and disgusting to come from one of the biggest players in the field, something Sandler has been for a very long time. You have to take notice when someone is this big, and it's only that much more infuriating when he delivers tripe like Jack and Jill.
Of course, that's just in the comedy, something that is the most subjective form of art imaginable. What I find funny is different than what you find funny. However, there's no denying the ideas that are put forth in Jack and Jill, the message Dugan and Sandler seemed to want to instill on their viewing public. That digs deeper than any subjective comedy bit can possibly imagine. That's the real reason movies like Jack and Jill cause hatred among so many of us, not because of how it's trying to keep its audience entertained but by what it's trying to say to them while doing so. No amount of surface-level makeup can make that attractive, but I don't expect Sandler or Dugan to understand that.