Jack and Jill (2011)

I want to start by acknowledging this is a bad movie. Very bad, in fact. Painful at times. But as bad as this was, it's nowhere near as bad as its reputation implies. This is a film with a 3% on Rotten Tomatoes which holds the record for the most Razzies "won." And... yeah, like I said, it's bad. I didn't like it, I didn't find it particularly funny, and I wouldn't want to watch it again. But after one viewing, it's not even my least favorite Adam Sandler holiday movie (though honestly that review seems so unnecessarily mean-spirited I'm inclined to rewatch Eight Crazy Nights to see if I was being too harsh, or at least as penance for some of the more hyperbolic statements). But based on what I remember, this is in line with other live-action Sandler films I've seen (many of which were also directed by Dennis Dugan).

Jack and Jill is bad. I don't particularly care for Adam Sandler as a comedian, and there is a laundry list of choices in this movie that were in poor taste then and an even longer list of decisions that aged abysmally. But at the end of the day, this feels like a bad comedy of its time, not the worst of all time. Not even close.

The movie, of course, features Adam Sandler playing twins Jack and Jill, whose names are unrelated to the premise (I guess Sandler just thought it would be funny to name them after the nursery rhyme). The actor who I'm pretty sure gets the second largest amount of screentime is (somewhat inexplicably) Al Pacino, playing a lovestruck version of himself. Actually, strike that "inexplicably" comment - he's stated he needed the money (though he also seemed to have a favorable impression of Sandler in that same exchange). He's one of several actors playing themselves in the film, including a cameo from Jared Fogel, a sequence that ages about as well as the infamous cameo in Home Alone 2.

In addition to Sandler and Pacino, Katie Holmes and Eugenio Derbez play significant roles, with Holmes playing Jack's wife and Derbez playing a landscaper who ultimately wins Jill's affections.

As you likely guessed from the presence of this review, the movie is set around the holidays, starting just before Thanksgiving and continuing through New Year's. This is actually one of the few areas I can genuinely compliment the film: they were attempting something interesting in how they approached (or more accurately didn't approach) Christmas. 

The movie features holiday decorations in the backgrounds of most shots... other than those at Jack's house. His family is Jewish, and presumably doesn't celebrate Christmas. I believe the holiday was mentioned only once in passing by Jack (in reference to work obligations), who seems to have no feelings about it one way or the other. As such, the movie offers a somewhat unusual perspective on Christmas: indifference.

Thanksgiving, Hanukkah, and New Year's are reference points the family celebrates. It's not unheard of for media to acknowledge families who don't celebrate Christmas, but usually there's either an attempt to confront its pervasiveness or contend with it in some other way. Seeing it left realistically as a background element that's ignored by the story and characters is a bit refreshing. Because "indifference" isn't all that unusual of a relationship people have with the holiday. This is a valid experience of the season that shouldn't be this rare on film.

Beyond that, the holidays serve the same generic purpose they usually do in family comedies: as a time of renewal and reunification. Granted, that would have more of an impact if the movie had been good, but we'll get to that.

Also, the movie opens and closes with documentary-style "interviews" with twins, highlighting different experiences. These seem like an homage (or perhaps knock-off) of the interviews with elderly couples in When Harry Met Sally, one of the all-time great Christmas comedies. These segments are odd - the twins are real, but the interactions feel scripted (I have no clue if that's actually the case). These seem to be present to rein in the tone (all the pairs of twins needle each other but care for their siblings). It doesn't really work - this isn't at all an accurate depiction of the dysfunctional relationship Jack and Jill have, so it's mostly just confusing.

Jack is more the POV character than Jill. He's a successful commercial director trying to book Al Pacino in a Dunkin Donuts ad, and his twin, Jill, is coming to LA for Thanksgiving. Jack finds his sister extremely unpleasant to be around, and - by virtue of being an Adam Sandler character - is physically incapable of concealing this or acting civil. His family likes Jill, and his attempts to undermine her fray his relationships with them, as well. 

Structurally, this is all a bit awkward. The movie seems to be modeling itself off a classic double-act, with Sandler's Jack serving as the straight man. Only Jack doesn't adhere to that role, and instead oscillates between that and just being another weirdo. It's not a situation where the characters trade roles over the course of the film (such as What About Bob?), but rather where Jack feels inconsistent. The movie doesn't seem to know what it wants him to be, so instead Sandler just does whatever he finds funny.

Eventually Pacino and Jill meet, and the actor is smitten. She doesn't return his affections, though she's also obsessed with finding someone to love her (an online dating site resulting in a blind date also fails miserably). Pacino, however, hasn't given up. 

In the hopes of leveraging his interest in Jill, Jack invites his sister on a New Year's cruise with his family, lying to everyone about his motives and plans. He tries arranging a meet up with Pacino, but by then Jill has figured out what he's up to. Since she won't meet him, Jack dresses as his sister and goes on the date in her place.

In the process he realizes he cares about his sister and decides to set things right. She's left by the time he gets back, so he brings his family to the Bronx on New Year's Eve to reconcile. He also brings the Mexican landscaper, who bonded with Jill earlier (unlike with Pacino, Jill seems receptive to his advances).

Okay, to the movie's credit, they cast Eugenio Derbez, a Mexican actor, rather than an American doing a racist accent and making stereotypical jokes. But he's still doing the accent and reciting offensive jokes I'm assuming were written by Sandler and co-writer, Steve Koren.

Speaking of offensive...

Is it worth addressing the homophobic and transphobic subtext? Is that even a fair description? I suppose a more charitable reading is possible. The movie seems to shy away from overt homophobic jokes, for the most part, which I don't believe is true of some of Sandler's other movies. There are even a couple moments in which the movie seems to be expressing something approaching solidarity, such as a scene where a bathroom attendant sees Jack go into a stall dressed as himself, emerge as a woman, then immediately helps him adjust his bra without saying a word (we'll ignore this doubling as setup for a gag about him mistaking Jill for the same character later). But for every moment that seems like it's implying body positivity, there's a cheap joke suggesting the opposite. It also seems telling that the movie avoids having Sandler's Jill kiss a male character (beyond some pecks on the cheeks).

But it's less the subtext than the humor that prevents this from working. That's not to say none of the jokes work - I chuckled a few times in the first twenty minutes - but even the stuff that works gets old fast. Though some of Pacino's scenes throughout are pretty good, mainly because of the actor's willingness to commit to whatever bit he's presented with. It's not so much they're funny individually, but there's a case to be made the movie is less a bunch of funny jokes than one big joke about Pacino being willing to do any of this. And, yeah, the Dunkin' commercial at the end was kind of fun.

It's nowhere near enough to redeem the film - my strong recommendation is you don't watch this unless you either find Sandler far more endearing than I do or are that curious about the prospect of Al Pacino co-starring as himself in an Adam Sandler vehicle. If so, it does kind of deliver on that front: it really is as weird as it sounds. But weird isn't always good, and - as much as I think this thing's reputation is exaggerated - it's neither something I enjoyed nor would recommend.