The saddest thing about Jack & Jill is that we allowed Adam Sandler to get to this point. The former SNL star started strong with raunchy silliness like Happy Gilmore and Billy Madison, then descended into a series of increasingly lazy and self-serving movies that ended last year with Grown Ups, a.k.a. The Time The Former Cast Of SNL Got Paid To Take A Vacation And Filmed It. For 15 years nobody has told Sandler no, and when it comes to his Happy Madison produced films, nobody has bothered to challenge him.
Now we have Jack & Jill, in which Sandler plays two equally detestable characters, one of them in drag, and threads the thinnest of plots through a series of sketch set-ups that almost instantly wear out their welcome. Jack is a successful Los Angeles advertising exec-- when was the last time a Sandler character didn't live in a giant house?-- whose twin sister Jill comes from the Bronx for Thanksgiving. Jill's character traits are pretty much the entire plot: she's fat and pushy, speaks in a nasal quasi-New York accent, doesn't understand computers or cell phones, can't get a date and just wants Jack's love, which he withholds to a degree that would make him the villain in any sane family comedy.
The only attempt at plot comes in the unlikely form of Al Pacino, whom Jack is trying to convince to star in a Dunkin' Donuts ad (it's just the tip of the gross product placement iceberg), and who inexplicably takes a liking to Jill, inviting her to his house for homemade cakes, a poorly planned indoor stickball game, and eventually a helicopter ride to the Spanish castle where he's preparing to play Don Quixote in Man of La Mancha. It's kind of brilliant to have Al Pacino bring his gonzo, nutbar performing style to a comedy, but Jack & Jill doesn't provide the goods, sticking Pacino in situations with limited potential, like answering a cell phone call in the middle of a Shakespeare performance, or speaking gobbledygook French to his waiter. Sandler doesn't make much of a sparring partner either-- even as the rambunctious Jill, he's weirdly reserved and unwilling, like an improv actor who won't pick up what his partner is offering.
It's not so much that the jokes in Jack & Jill aren't funny, which they uniformly are not, or that the premise is silly. It's that there's absolutely no effort at creating characters on which to hang this flimsy story, saddling Jill with a bunch of annoying quirks that don't add up to any real human being, and letting Sandler react to her with such hostility and unaware, shmucky selfishness that you start to assume this must be a reflection of him in real life. The movie is too lazy to even come up with supporting characters-- Katie Holmes is the standard-issue scolding wife, and then the rest of the cast is either Sander favorites with a handful of lines (David Spade, Nick Swardson, Tim Meadows, Norm MacDonald) or some of the most random celebrity cameos you've ever seen, from Shaq to Jared the Subway Guy to Kris Jenner to, swear to God, Johnny Depp. Nobody is acting, or even seems to particularly care they're onscreen. They're collecting paychecks and tossing the result at the audience they're confident will lap it up.
Directed with the customary lack of effort by Dennis Dugan and slopped over with sticky sentimentality in its final moments to mask its overall meanness, Jack & Jill is so bad that you know the people who made it knew better, but simply didn't care enough to fix it. They're pandering to anyone who ever bought tickets to a Happy Madison production, and by buying into this one, you'd only be encouraging them to get worse. Stop the madness. Avoid this.