Lasciate ogne speranza, voi chi’intrate. How did it come to this? At the height of his power in Hollywood in 1999, Adam Sandler founded his own production company as a way to continue making the movies he enjoys. Over the years his films have slowly morphed into a pariah on the landscape of big budget studio comedies, becoming thinly veiled excuses for lavish vacations. But do they truly represent the nadir in the career of one of comedy’s once-brightest stars? Are there any hidden or underrated gems? Is there such a thing as too few fart jokes? Will I retain any sense of sanity by the end of this? Join me and find out, as we venture to the Happy Valley.

Long, long ago when this project was in its infancy, I had already looked ahead to Jack and Jill with disdain. Despite never seeing the film before, I was familiar with its reputation and the black mark it represented on Adam Sandler’s career. I specifically avoided seeing it upon its release because I could already predict what kind of movie it would be. Could the film possibly live up to the hype or, perhaps more accurately, anti-hype? Critics unsurprisingly, hated the film, placing it at or near the top of their Worst Films of 2011 lists. Sandler, no stranger to the Golden Raspberry Awards (or, the “Razzies”) made history as the film swept in all categories — including Sandler as Worst Actress. (He plays both sides of a twin-sibling duo, you see.) Jack and Jill was the first film to do so, although Sandler did win Favorite Movie Actor at the Kids’ Choice Awards the same year. And yet Jack and Jill defies logic by simultaneously transcending its stupidity and falling short of it.

While I would agree that the film is only technically a comedy, that’s simply because it cannot be classified as anything else. Sandler is perhaps the least funny he’s ever been, in both of his roles, and the film never allows any other actor enough oxygen to make any kind of impression — with one notable exception, which we’ll get to in a bit. As bad as his movies generally are, Sandler at least is generous enough to share the comedic burden with his castmates. Here, with twice the attention, Sandler is the albatross around the film’s neck, killing any hope of momentum or the audience’s attention with his incessant shtick. The film is filled to the brim with needlessly long scenes of endless banality masquerading as jokes. “Look at what I’m doing! Isn’t it silly?” Sandler seems to be saying to us, without actually putting any effort into the script (which he co-wrote, by the way). I was shocked at how boring the whole affair is.

Beyond those cardinal sins, the film is incomprehensibly put together. At several points, I had to rewind the digital copy I had rented ($4 I’ll never get back) because it felt like I had missed an important development or a key bit of dialogue. Sadly, I was mistaken, and the result was having to spend even more time with this film than necessary. Consider the transition between the dreadfully long Thanksgiving dinner scene and the one that follows: Jill gets up to leave the table, and the film immediately cuts to her running away in the woods carrying what looks like a goose. Scenes tend to move from one to the next, almost at random, with no discernible rhyme or reason. This makes the film not only frustrating to sit through, but hard to understand; it’s not that the film demands constant vigilance, but still … it’s a lethal combination.

Jack and Jill was produced with a $79 million budget and grossed nearly $150 million worldwide; I feel like a broken record about this, but all of this is in spite of the massively critical reception, of course. I’m no expert in the financials of movie production, but how could such an expensive film look like it was filmed on cheap soundstages? Yes, the film is filled with movie stars, but so are many other mainstream comedies. Product placement has always come front and center throughout these films, but here there are logos practically watermarked in the corner of every frame. That’s expected to some extent in a film centered around advertising executives, and while it never becomes downright hawkish, you always manage to notice it whenever it’s presented. 2011 was chock full of memorable comedies that exceeded expectations, Jack and Jill, on much smaller budgets. Bridesmaids, Horrible Bosses and No Strings Attached were all R-rated comedies that operated on budgets of less than half the size of Jack and Jill, which was rated PG and released around the holiday season. Sure, those movies weren’t full of Big Movie Stars (or at least weren’t at the time), but if Sandler actually cared about his creative output, he could have taken a minor pay cut to, at the very least, get inside the actual Staples Center for a scene at a Lakers game, instead of half-assing a green screen. Make no mistake, Jack and Jill deserves every ounce of the bad reputation it’s built up. I don’t know if this film contains the outright contempt for its audience that other Happy Madison films are known for, like Grown Ups or Just Go With It, but there are certainly elements of it that can make the argument.

And now, to end on a positive note, we come to one Alfredo James Pacino. To this day, I have no idea why Pacino would choose to be in a Happy Madison film. Maybe he was a longtime fan of Sandler’s. Maybe he wanted to display his range and do an outright comedy for the first time in his career. Maybe he wanted to surprise his critics. Maybe he received a large chunk of the budget that was left over after Sandler was done with it. Either way, Pacino remains the brightest spot amongst the dim offering that is Jack and Jill. I’ve always had an affinity for actors portraying themselves onscreen, and Pacino’s version of himself here is delightfully deranged. Almost 20 years after collecting his Best Actor Oscar, Pacino is much better than he needs to be for a film of this caliber, turning himself into a lovesick puppy who just can’t get enough of Sandler as Jill while also poking fun at his own persona and other Serious Hollywood Actors. His scene where he interrupts his own Broadway play was the only scene I found remotely humorous. The great tragedy of Jack and Jill is that the rest of the film can’t rise to Pacino’s level because his “character” is given a level of nuance and comedic insight sorely lacking elsewhere. Pacino’s legacy and reputation would survive Jack and Jill. Sandler’s wouldn’t.

  • “I’m Getting Paid How Much?!” Inexplicable Cameo Award: There’s a ton of cringe-worthy options here, including Johnny Depp and a certain former Subway spokesperson who shall remain nameless, and *rolls eyes* John McEnroe. The film marked the last movie appearance of Regis Philbin and includes a wordless pre-transition cameo from Caitlin Jenner. However, I’m bending my own rules a bit and giving this week’s award to Katie Holmes. Yes, her role technically extends beyond a cameo appearance, but her character somehow has less importance to the film than anybody mentioned above.
  • Just Go With It — The Happy Madison Promise: I’ve seen many reviews mentioning that Jack and Jill is one of Sandler’s most racist films. I can’t argue with the implication, especially given the romantic subplot between Jill and a Hispanic groundskeeper, but it’s hard to beat the undercurrents of some of Sandler’s earlier films.
  • Fart Joke Counter: Two — one each from Jack and Jill simultaneously — plus one extended post-Mexican-food bathroom scene.
  • The Walkout Test: This one’s a pass.
  • NEXT TIME: Sandler gets edgy in the R-rated That’s My Boy.