Jack & Jill doesn’t stray far from the Adam Sandler canon: a guy who lives in a big house complains about a problem while a sweeping score plays in the background, a child punches an adult, there’s dick jokes, and somebody rides a WaveRunner in a swimming pool. The thing that distinguishes Jack & Jill from his other comedic films is that Adam Sandler, in drag, plays his own twin sister. Critics might decry Sandler’s film as the lowest hanging fruit, but I see it as comic gold. I find Sandler hilarious in general, but I’d be lying if I said that seeing his portrayal of Jill didn’t make me laugh. Sandler’s comedy isn’t brainy, and he doesn’t have delusions of artistic grandeur like other comedy titans (I’m looking at you, Jim Carrey), but that’s why I will inevitably plunk down a handful of dollars to see Jack & Jill. I laughed my ass off when Happy Gilmore went at Bob Barker with a golf club, and I will laugh just as hard when Jill flattens a mini-pony. I don’t want to think about why I found the gag funny, and whether or not that makes me some sort of morally backwards heathen that can’t recognize my own privilege, etc. The fact is, it’s funny because an ugly lady flattened a tiny horse–what more could you want?
But it comforts me to know that when I saw Jack & Jill, I wasn’t alone in the theatre, and that’s because Sandler was counting on his past success, as well our collective cultural fascination with comedies where men dress up like women; most have been undeniably successful. Would you remember anything other than Marilyn Monroe in Some Like it Hot if Tony Curtis and Jack Lemon hadn’t donned dresses? Has anybody ever been able to steal the spotlight away from Robin Williams in a film quite like Nathan Lane did in The Birdcage? And would White Chicks have grossed $70,831,760 dollars in America if it were, well, really two white chicks instead of two Wayans brothers in wigs? The answer is always no. Numbers don’t lie, and they prove that people have and will pay good money to see leading men become leading ladies.
Movies from Nuns on the Run to the entire Madea series are funny to people because they feature men that don’t make good-looking women, and to make it worse, they make sure the wardrobe consists of things they found in your grandmother’s closet. In Jack and Jill, Adam Sandler, playing his own twin sister, isn’t an ugly man, but like Robin Williams, Tyler Perry, and Patrick Swayze in Too Wong Foo, Thanks For Everything! Julie Newmar, Sandler makes a particularly misshapen woman.
Drag is the ultimate comedic compromise: the comedian can’t rely on his usual wiles for a laugh, because the comedian is the laugh. Larry David and Ricky Gervais, the reigning kings of funny-yet-unpleasant experience, remain separate from the things that make them funny. Watching Chris Wayans get hit on by a lecherous admirer is hilarious because he can’t pull his blouse and latex mask off–the joke is embodied and thus inseparable from the performer. Adam Sandler’s transformation into a Jewish aunt is funny on its own, but when he gets hit on by Al Pacino, the fourth wall is stretched to its limit; the entire scene is almost too creepy, but the joke relies on our shared understanding that suffering underneath that wig is beloved comedian Adam Sandler. It’s only slightly less weird than if Al was hitting on the real, male-identified Adam Sandler.
Impersonating women for a laugh is a method that can be traced back through centuries of theatrical history. Charlie Chaplin and Stan Laurel brought the tradition with them to America, and cross-dressing has since been a central plot device for dozens of American movies, but none have reached the level of highbrow success quite like 1982’s Tootsie. Nominated for every big award at that year’s Oscars, Dustin Hoffman’s portrayal of Dorothy Michaels is timeless, but also impossible to replicate. As far as drag comedies go, it’s the Gold Standard. That doesn’t mean the bar can’t be raised, but there is a strong enough argument for not raising the bar at all. Adam Sandler has figured out that a film’s commercial success is generally reliant on a proven equation: (Silly)X + (Silly)Y = Laughs. Sure, (Silly)X + (Silly)Y + Wig + Fake Boobs = Laughs is a departure from his usual methodology, but I don’t believe Jack and Jill is meant to be the next Tootsie. It isn’t supposed to be meta, or even smart; it’s not a mockumentary about famous, eccentric twins, and it isn’t an ironic portrayal of a culturally relevant archetype; instead, it’s a convincing argument for the power of a simple punchline. In the great tradition of Mrs. Doubtfire, Too Wong Foo, and The Birdcage, Sandler’s not angling for an Oscar, he’s just doing what he knows, and that just so happens to be making a fool of himself for the sake of comedy.
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