Greetings and welcome back to Raspberry Picking, where we look back at Golden Raspberry Award winners and nominees and decide whether they really deserve to be called the worst movies of all time. This month, we’re tumbling down the hill with Jack and Jill, nominee for every single Razzie and winner of…every single Razzie.
We tackle some controversial issues here at Raspberry Picking. War, Nazis, feminism, Lindsay Lohan, Joe Eszterhas, the absolute nadir of American politics. It can get a little tiring, walking on all those eggshells. So for this month’s column, I’ve decided we should discuss a matter guaranteed to cause no drama or consternation whatsoever: men dressing up as ladies in the movies.
Where it all began, according to Razzie voters.
Drag in the movies is nearly as old as the movies itself, with female impersonator Bothwell Browne’s starring role in Yankee Doodle in Berlin (1919) as one of the first high profile examples. But as with all filmmaking trends, drag roles have gone through their ups and downs and phases everyone wishes we could all just forget about. In the late 1990s through the 2000s, that phase was called “male comedians playing multiple roles, some of which were caricatures of women.”
The trend is older than the ‘90s, of course. Role doubling in theatre is as old as theatre itself, and since the earliest Greek actors were all men, the “trend” would have been the norm. The earliest example I know of on film is Kind Hearts and Coronets (1949) (I’m sure there’s an older example, Tim’s the film scholar, don’t yell at me), in which Alec Guinness plays eight different roles. In its heyday standard-bearer for this sort of doubling was Eddie Murphy, whose repertoire from this time period included The Nutty Professor (1996) and its sequel The Klumps (2000), blessedly finishing with Norbit in 2007. He passed off the crown to Tyler Perry, who first starred as Mabel “Madea” Simmons in Diary of a Mad Black Woman (2005) and continues playing the character to this day. With a few exceptions, one thing you may notice about these films is that they weren’t exactly regarded as great films in their day, and they’re not exactly remembered as great films now. I tell you all this to illustrate why, when Adam Sandler suddenly decided to try his own hand at being Tyler Perry in 2011, the world might not have been inclined to greet it with open arms.
The tagline on the poster is considerably meaner than anything in the movie proper.
Pre-Jack and Jill, Adam Sandler had spent nearly two decades establishing himself as the Michael Bay of comedy films: critically scorned, but extremely bankable. His first leading role in Billy Madison made back more than double its budget, and his second in Happy Gilmore did triple. With a few exceptions, the further one gets from these two films, the worse his reviews, and the bigger his budgets. By the time he and long-time collaborator Dennis Dugan were in pre-production for Jack and Jill, his standard budget had ballooned to about $80 million. If one believes the guys over at Red Letter Media, Sandler and Company spent most of this money on exorbitant salaries for themselves and very little of it on the actual film.
When Jack and Jill hit theaters, it got the usual Adam Sandler treatment, but kicked up a few notches. It currently sits at 3% on Rotten Tomatoes and broke the record previously held by I Know Who Killed Me for Razzie wins. In a shining example of how unserious Razzie voting is, the Razzies shoehorned Jack and Jill into the “Worst Prequel, Remake, Rip-off, or Sequel” category by labeling it a “remake/rip-off” of Edward D. Wood, Jr.’s Glen or Glenda, a movie to which it bears no resemblance whatsoever except for the presence of a male actor in a cheap feminine wig. But despite the obvious bad faith, no one has been overeager to go to bat for Jack and Jill. It was savaged by critics as the low point of Sandler’s career, and especially now that Sandler has a Razzie Redeemer nomination under his belt, that reputation appears to have settled comfortably into the mold of accepted truth. So what do we think? Will we break that mold today?
THE STORY
You know what? Yes. Yes we will. Jack and Jill officially belongs in the category of “got done dirty.” Not only is it not the worst Adam Sandler movie by a long shot, not only was it not the worst picture of 2011, it’s…kind of okay? It commits enough blockbuster teen-boy-targeting comedy sins to never rise above that level, but for a movie I was expecting to despise so much that it would make Freddy Got Fingered feel like My Cousin Vinny, I’ll take “kind of okay” as a miraculous success.
In the middle: you. On the sides: me.
Of course, it takes its sweet time achieving its “kind of okay” peak. Jack and Jill opens on a montage of sets of twins describing what it’s like to be twins. Some of these twins discuss their “twin superpowers.” Others of these twins take unsubtle potshots at each other for being annoying and fat. None of these twins are even slightly funny. I am shockingly relieved when Adam Sandler appears for the first time.
Jack Sadelstein (Sandler) has everything a man could want: a lucrative job in a hotshot LA ad agency, a beautiful wife named Erin (Katie Holmes) whose entire purpose in life is to exist in his house until he needs a dose of womanly wisdom, a gardener named Felipe (Eugenio Derbez), and two surprisingly-not-annoying children (Elodie Tougne and Rohan Chand), the younger of whom has a penchant for taping things to himself. Unfortunately, Jack also has a twin sister, Jill (Adam Sandler), who visits for Thanksgiving from their old stomping grounds in the Bronx every year and who is, to put it mildly, a bit eccentric.
Adam Sandler playing an ugly, overbearing Jewish stereotype, and also Adam Sandler playing a woman.
Whether or not Sandler intended to have weird incest vibes in his movie about twins, they unfortunately loom rather large. Jill has always felt starved for the attention and favor of her more popular, more socially adept (so we are told) brother. She has decided to make a power play by booking an open-ended plane ticket so that she and her beloved cockatoo Poopsie (probably Adam Sandler) can stay with his family through Hanukkah. Everyone else in the family already loves Aunt Jill, so this is far less of a sacrifice than Sandler and Koren seem to have wanted it to be, but that just means everyone else can be lovingly indulgent of Jill’s increasingly wild antics while Jack suffers in his lonesome embarrassment.
Jack is suffering elsewhere too, because his ad agency, which he runs with Ted (Tim Meadows) and Todd (Nick Swardson), for poorly explained reasons, needs to get Al Pacino (himself) to star in a commercial for a new Dunkin Donuts sugar syrup milk coffee beverage called the Dunkaccino. Pacino sort of rhymes with Dunkaccino, they explain, because that’s the kind of highly skilled creative professional these gentlemen are.
So Jack is trying to get Jill out of his hair and worm his way into the affections of Al Pacino at the same time. Jill, in the meantime, being a middle-aged lady with needs, has decided she’s ready to find love. You’ll never guess how these two plots intersect, and I’ll only say here that I hope to one day be paid as much for something as Al Pacino was paid to wear an Osama bin Laden beard and profess his undying love to Adam Sandler.
Sandler got a ridiculous number of his pals to be in this thing.
THE BAD
If I just write “Adam Sandler” here, will you all understand the shorthand?
At least the horse isn’t jizzing this time.
All the usual unfunny stuff Adam Sandler does, he does here. Well, maybe not all of it. We’re blissfully spared his mosquito-whine old man voice from Eight Crazy Nights and the joyful sight of him teaching a five-year-old to pee on doorjambs from Big Daddy, but we still get plenty of opportunities to gouge our eyes out when the script by Sandler and Steve Koren insists that we must find chimichanga-induced diarrhea the peak of hilarity. We do not, in case that was not clear.
I do not terribly wish to do a rundown of every single wretched joke in Jack and Jill; it would be tedious for you and make me want to stick my head in a trash compactor. Instead, we can also talk about Dennis Dugan’s direction, which is as lifeless and uninspired as anything this side of a mid-tier Netflix original. Dugan had been making movies long enough by 2011 to learn that sometimes, as a film director, you’re supposed to direct the camera, but he has not learned how. The camera in Jack and Jill wanders around like a lost puppy, suggesting at times that someone might have forgotten to put the brakes on a dolly.
We could also talk about Katie Holmes, and the painfully nervous grimace she wears throughout Jack and Jill, suggesting she thinks Sandler and Dugan might at any second order her to eat dog feces Pink Flamingos-style. We could talk about the alien-looking lighting in every shot where Jack and Jill appear together. The shot composition, organized by cinematographer Dean Cundey of Who Framed Roger Rabbit fame, is actually pretty good, but the different lighting on the two versions of Sandler in the stitched-together scenes makes Jack and Jill look like they exist in different states of matter.
Gas and solid, if you take my meaning.
We could talk about the complete waste of Waddy Wachtel, a gifted guitarist and producer who deserves better than to be wasting away on the pointless scores of trashy comedies. We could talk about a near-unbearable running gag at Felipe’s family reunion that involves his one-toothed abuela (Eugenio Derbez, doing a Sandler) being knocked out and resuscitated with hot peppers.
We could also talk about the terrible, horrible, no-good, very-bad cockatoo. The one who chugs a bottle of Jack Daniels and tries to drown itself in a chocolate fountain. The one who speaks in something much too close to Sandler’s Eight Crazy Nights voice for comfort. The one I was certain was going to be the subject of tasteless animal abuse. But miraculously, it isn’t, so we won’t.
But I will make you look at it in low resolution.
THE GOOD
Instead, we’ll move on to the good stuff, which has far fewer column inches already devoted to it.
So don’t get me wrong; the bad stuff in Jack and Jill is bad, the sort of bad that feels like a personal attack on you and everyone you love. The diarrhea sequence alone would prevent it from rising above three stars. But the flip side is true as well: there’s good stuff here, and it’s good, funny jokes and interesting choices and, dare I say, even a little metacommentary that is unobtrusive enough to (mostly) not grow tiresome.
There’s a reason I compared Sandler to Tyler Perry up top, rather than Eddie Murphy or any other purveyor of this weird comedic subgenre. Having seen (and not enjoyed) one Madea film, Madea Goes to Jail, I am hideously unqualified to discuss them, but every time Perry releases one of them, two things happen: critics savage it, accusing Perry of perpetuating anti-black stereotypes and misogyny against black women, and it makes ludicrous amounts of money, much of it from black audiences. It’s by no means universal, but Perry’s black fans seem to regard Madea as a loving parody-homage to beloved grannies and aunties, Perry’s own included. Again, not qualified to do more than speculate wildly, but I would not be surprised to learn that Sandler – a Jewish comedian in a long tradition of Jewish comedians who has always put his Jewishness front and center – was attempting to do the Tyler Perry Madea “thing,” but for Jewish audiences, with Jill Sadelstein. And you know, this here Jewish audience member kind of bought it.
More than Adam Sandler buys that he’s looking at a real human being in either half of this shot.
The premise of the film sets us up to expect Jack and Jill to treat Jill with petty cruelty and call it comedy, but the actual film is rather warm and loving towards Jill. She is, in many ways, an overt Jewish stereotype, a combination of the stereotypical Jewish mother and the Jewish-American Princess: loud, overbearing, New York-y, socially oblivious, nagging, neurotic, and entitled. At the same time, she’s kind, big-hearted, and free-spirited. Jack quickly jumps to Jill’s defense whenever someone not in his family points out any of her worse attributes, and for all his kvetching about her, seems to sincerely believe that Jill deserves to find someone who will appreciate her. Fright wig aside, costume designer Ellen Lutter aids these intentions by dressing Sandler in elegant, muted eveningwear that actually flatters him, especially in Jill’s scenes with Pacino.
I would say “better love story than Twilight,” but I like Twilight too.
At the end of the movie, when Jill finds love with Felipe, the movie treats this as something to celebrate and suggests that they will be happy together, rather than condemning Felipe to the fate of legions of henpecked, beleaguered Hollywood comedy husbands in the ages before and since.
Maybe to you, Sandler seems to be saying, Jill just looks like a bunch of stereotypes in a plus-size dress. If that’s the case, it’s you who refuses to look underneath them and see the fully-realized woman we created. And if you can’t get there, that’s your latent anti-Semitism talking, not mine. He shows his work further with Felipe, played with disarming sweetness by Eugenio Derbez, who speaks almost entirely in jokes about illegal immigration designed to make the other characters uncomfortable until he assures them that he’s just kidding. This is only intermittently successful (see the note about the one-toothed abuela), but when it lands, it lands hard, and it does so several times. A remark Felipe makes about his dearly departed wife sneaking across the border of Heaven made me laugh, and then made me realize I was enjoying the film.
Maybe you don’t buy it. That’s your right. But I think Sandler’s onto something about the way some culture critics tend to reach for their smelling salts every time they see a gag that incorporates a stereotype. Sometimes we’re being asked to laugh at those stereotypes. Other times, we’re being asked to laugh with them. Other other times, we’re being asked to laugh at the people who can’t see past them. I appreciate the effort, even if it occasionally falls flat.
Very, very flat.
Also, Al Pacino’s Dunkaccino rap is only the second best thing in the movie involving Al Pacino. The best thing is a moment where Jill accidentally breaks his Oscar statuette, and then reassures him that she’s “sure [he] has others.” The look on Pacino’s face as he responds? Worth a month’s Netflix subscription by itself.
What’s the point of being a movie legend if you’re not going to debase yourself from time to time?
Maybe everyone was tired of Adam Sandler’s Adam Sandler-ness at this point in his career. Maybe our patience with the male-comedian-plays-his-own-female-counterpart gimmick had grown thin. Maybe both. Whatever the reason, Jack and Jill was the Adam Sandler film that finally drained everyone’s Adam Sandler tolerance. And that’s a damn shame, because Jack and Jill is probably my favorite Adam Sandler comedy. Admittedly, that’s like trying to select my favorite flesh-eating bacterium – but no, I’ll go a step further and actually say that I’m rather fond of Jack and Jill. There’s an intelligent emotional core to Sandler’s stupidity this time around, the same elusive creature that one can see flittering around the edges of his other higher-tier movies, Punch Drunk Love and Spanglish. The main difference is that neither of those movies came along at a time when the world felt like giving Adam Sandler and everything he represents a good wallop. Some movies need their context to make sense; others benefit from being judged in a vacuum. I guess that means we can all agree, for different reasons, that we ought to eject Jack and Jill into outer space.
Quality of Movie: 2 / 5. Charms or no charms, this is not a work of high craft.
Quality of Experience: 3 / 5. But unlike some other works of low craft that we could name, it does have its share of charms.
Mandy Albert teaches high school English and watches movies – mostly bad, occasionally good – in the psychedelic swamplands of South Florida. She is especially fond of 1970s horror and high-sincerity, low-talent vanity projects. You can listen to her and her husband talk about Star Trek: Enterprise on their podcast At Least There’s a Dog! You can also follow Mandy on Letterboxd.