Reserved Seating Goes All Pacino: JACK AND JILL

by Adam Riske and Rob DiCristino

The review duo who want to play stickball in The Bronx.

Adam: Welcome to Reserved Seating. I’m Adam Riske.

Rob: And I’m Rob DiCristino.

Adam: This week, our Al Pacino series continues with a re-examination of 2011’s Jack and Jill, the Dennis Dugan-directed comedy starring Adam Sandler, who plays the titular identical twin brother and sister. They hate each other but they also love each other and that’s pretty much the movie. Jack and Jill co-stars Katie Holmes (showing impressive patience) as male Sandler’s wife, Eugenio Derbez as female Sandler’s love interest, and our guy Al Pacino playing himself in a game of self-parody. Jack and Jill was the movie where Adam Sandler broke an unwritten contract with a lot of moviegoers, myself included. People were fine with him making dumb comedies (his previous two movies, Grown Ups and Just Go With It, made money despite being bad movies), but Jack and Jill was the one where he seemed openly contemptuous of the audience. Jack and Jill feels like Sandler using a movie as a practical joke to see what’s the lowest amount of effort and goodwill he could give audiences before they stop rewarding him. It’s an ugly display.

This was my second viewing of Jack and Jill after seeing it in theaters in 2011. Nine years ago, I found it to be groan-inducingly bad with a few slivers of entertainment here and there. I didn’t get as riled up on this recent viewing because I knew what to expect and I was watching this more as an Al Pacino fan than an Adam Sandler fan. I think Pacino is kind of great here, despite being in a movie that’s not worthy of him. I’m in the bag for Schmoopy Al after seeing his desperate romantics in movies like Sea of Love and Frankie and Johnny. He’s pretty much doing the same thing in Jack and Jill but with Adam Sandler instead of Ellen Barkin or Michelle Pfeiffer. After watching a new Pacino movie every month for three years with you, his performance in Jack and Jill feels weirdly celebratory (“Don’t you just love Al Pacino?”) while arguably also humiliating him? Does it humiliate him? He’s clearly in on the joke. As bad as Jack and Jill is, the Pacino moments are good enough for this not to go down as one of the worst Al movies for me like The Humbling or Hangman. The moment where his Oscar breaks and Jill says something like “You must have more of those” and Al replies “You would think so” makes me laugh.

What did you think of Pacino in Jack and Jill?

Rob: This was my first viewing of Jack and Jill. It’s definitely a lazy movie. It has very little respect for its audience, for sure. It’s full of useless celebrity cameos and more product placement than even its premise can excuse (best chronicled by Red Letter Media here), but I was actually expecting it to be a lot worse. It’s not the worst movie ever made. It’s not the worst movie of 2011. I wouldn’t even put it in the bottom half of Sandler’s filmography. To be clear: Jack and Jill isn’t good, and no dignified society would sanction its buffoonery, but I didn’t hate myself the entire time I was watching it. That should count for something.

I’ll answer your Pacino question plainly: I think this is one of the best Pacino performances of the 2010s. What compelled him to make this? Probably money. Maybe he heard that Sandler is fun to work with or that each Happy Madison production is essentially a cast vacation. Regardless of his reasons, he is the beating heart of this movie. He’s in this to win it. You brought up the “broken Oscar” moment, which was great, but I actually had to pause the movie to laugh out loud when he tells Jill, “I used to raise pigeons. No, wait. That was Brando.” I wasn’t expecting anything like that.

I need a second here, in fact, because there are so many layers! Pacino is a great actor choosing to be in a silly movie in which he plays himself. A caricature of himself, actually, one that pokes fun at his perceived idiosyncrasies as a performer and public figure (the costumed Broadway stuff, the crazed home behavior). He falls in love with a woman played by a man, whom he woos, in part, by talking about his acting philosophy. He inspires Jack (in the in-universe guise of Jill) to love his sister for her willingness to give him the spotlight rather than take it for herself. He’s praising Jill for being a genuine person in a cynical world, a generous actor in a production that is beneath her. He then performs brilliantly in a tacky, obnoxious Dunkin’ Donuts commercial before declaring to Jack (who could easily be Sandler in the editing room) that no one should ever see it. Are there two Pacinos, as well as two Sandlers? Where does one end and the other begin? Pacino is the spinning Inception top of Jack and Jill. I’m going to need more time to unpack this.

Adam: It’s one of those running gags in movies where while I’m watching it I chuckle barely but when I think back on it it’s really funny. Like how Pacino keeps calling Adam Sandler’s Jack “popcorn” because Jack gave Pacino’s daughter his popcorn once after she spilled it, or how Pacino’s wooing becomes as palatable as Pepe Le Pew to Jill. Comedy is weird. I’m noticing that a lot more about me when I watch comedies. Things are conceptually funny and that’s somehow more edifying than it actually making me laugh out loud. I’m going to drop a bomb on you (for the record, I still don’t like this movie): Adam Sandler is giving half of a good performance. It’s easy to equate him being shitty and lazy because that’s how he plays Jack, but his portrayal of Jill is arguably three-dimensional despite being entirely obscured by constant buffoonery.

Rob: That was actually my next note. He uses Jack as a straight man whose job is to lure the audience into hating Jill, but the turn comes as he slowly humanizes her and reframes Jack as the intolerant one. The fact that Jill holds firm and never accepts Pacino’s advances felt like a subversion, in a way. If Sandler and co-writer Steve Koren were really just cashing a paycheck, they would have played it straight: Jill would be a lonely, aging, unattractive girl with no self esteem who settles for Pacino because he’s Pacino and she has no other options. She’s honored by it, in fact. In service of that, the entire movie would have devolved into a non-stop barrage of transphobic/homophobic jokes. There would, for sure, have been a cringy sex scene between Sandler and Pacino featuring all kinds of “He actually has a penis!” winks to the audience. It would have been truly reprehensible. Again, Jack and Jill is a bad movie. I never want to see it again. But it has moments of warmth and restraint that lazier filmmakers would not have included.

Anyway, who’s your favorite completely wasted performer in Jack and Jill?

Adam: I think Eugenio Derbez is pretty funny normally. I He just seems like he’s having the time of his life. I dunno. I also was noticing that Katie Holmes is pretty, which is not usually something I preoccupy myself over. That’s about it.

Rob: I kept watching her do nothing in scenes and wondering what she was thinking about.

Adam: There should be a Dinner For Five episode of every actress who played “attractive wife” in an Adam Sandler comedy just talking about how they prepared for the role and what it was like having to bury every instinct and acting choice because nothing was required.

Rob: “Just think of the free Carnival Cruise,” she repeated to herself. Anything else on Jack and Jill?

Adam: I found the old age makeup on Derbez when he played his own grandmother to be absolutely terrifying.

Rob: I liked the running gag where Jill insists movies have different titles. He uses it just the right number of times. What are we watching next week?

Adam: Next week we’re back with another box office bomb: Kathryn Bigelow’s largely forgotten K-19: The Widowmaker. I blame the title. Until next time…

Rob: These seats are reserved.