“Jack And Jill” begins with the disingenuous tactic of employing real footage. First, the credits run over real life fraternal twins discussing their similarities, differences, and difficulties with each other. Most are affectionate, jokey, even somewhat stagey, but even if they did hire actors, the effect of seeing such open affection between two people similar in dress, speech and attitude is a gopher, an automatic connection with audiences.
If the real people don’t have an affect, maybe babies will, as the segue to the real story shows a brother and sister from birth to high school. Both have the same attributes, but one is an average Jewish boy, the other a mannish, bouffant-haired female doppleganger. This footage is seen through family video, another cheap tactic to get the audience ready to swallow the most improbable of possibilities — we’re going to spend the next one hundred minutes staring at Adam Sandler pretending to be a girl.
Normally Sandler's movies bend over backwards to accommodate his obscene desire to cram films with brand names and products. Here, he finds a logical out: his Jack is a harried television commercial director for pretty much every product under the sun, most of which get prime real estate on-screen. Perhaps Peptol Bismol should be credited over Dana Carvey, the latter of whom appears in a ridiculous wig and makeup for two brief lines standing behind Regis Philbin.
Jack is stressed because his nosy single twin sister is about to visit. Jill, who looks just like Sandler but has the affectations of an old Jewish grandma, is oddly, warmly, treated not as a joke, but as a living, breathing human being. Jack picks her up from the airport and she proceeds to passively-aggressively invite herself over, occupying Jack’s life by hogging the bathroom, making awkward dinner table discussion, and generally reacting like a dim bulb shut-in who doesn’t understand simple concepts like the internet or pop culture. Despite the movie’s attitude of “this is happening, deal with it” as opposed to “look at these wacky shenanigans!” we’re forced to understand her as a real person. But Sandler’s exaggeratedly comic older-lady mimicry does no one any favors. It’s the first time him and director and longtime collaborator Dennis Dugan don’t seem to be on the same page.
Meanwhile, Jack’s facing pressure at work because he’s about to lose Dunkin’ Donuts as a client, as they’ve given him the implausible ultimatum that he needs to score Al Pacino do to a DD spot. This leads to Jack’s pursuit of Pacino, here playing himself, and when they come face to face, Al’s more fascinated by Jill’s unconventional… beauty? Pacino’s lust has no bounds, and, after an innocent Lakers game flirtation (with a tone-deaf cameo from Johnny Depp, wearing a Justin Bieber t-shirt), Pacino is breaking out cell phone tag, birthday cakes and even helicopters to get his girl.
“Jack And Jill” will be noteworthy in ten to fifteen years as the moment Pacino really cut loose in the world of the low-brow. Even for the guy who was in “Gigli," this is a career low, not for his performance (spirited, game), but for the man’s intentions. People get involved in Sandler films because they want to expand their brand, which explains Continental Cruises, Oreos, and every other main commercial label that appears in “Jack And Jill." With Pacino, he’s trying to expand his demographic, to get younger viewers to embrace the Pacino catalog. How else to explain the multiple references to “The Godfather”? Does Jack really need to watch extended sequences from “Scarface” to “research” Al Pacino, and do we need to see him do it? Pacino eventually says he’ll do the commercial if Jack can get him the unwilling Jill, and there’s the sad suspicion that “Jack And Jill” negotiations went something like that.
As usual, Sandler maintains his “nicest guy in Hollywood” rep by employing his very good friends, none of which can maintain a career on their own. David Spade appears in convincing drag, Norm MacDonald participates in a laugh-less blind date with Jill, and Nick Swardson, Tim Meadows and the Happy Madison bit players all get a moment to, ahem, shine. But, in a new wrinkle, Sandler attempts to diversify, with Latin comedian Eugenio Derbez as a Mexican landscaper working on Jack’s yard. The wide-eyed, rat-faced Derbez constantly makes offensive jokes about being an illegal immigrant before shouting, “I’m just KEEEEDING!” Holy shit, it’s Ferrecito. Later, he’ll take Jill to a Mexican picnic, where the entire family is named after variations of Juan and Jose (“Just KEEEDING!” he says) and they breakdance on folded cardboard boxes.
Like Tyler Perry’s films, where Perry plays a number of characters in hideous drag, when Sandler’s only playing himself, he seems exhausted. His last five or six movies featured performances that were lazy, uninspired work, but here, the poor guy is every bit his forty-five years, forced to play alongside a screeching feminine nightmare version of himself. There’s no relief from the likes of Katie Holmes, in the thankless role of Sandler Wife and getting even less to do than previous Sandler spouses. You wonder if, at some point, it might be time to try something different. This hell cannot go on. [D]