I Watched “Jack and Jill.”

It’s no secret that Adam Sandler’s Happy Madison Productions has produced many terribly received movies, from Grown Ups, Grown Ups 2, Pixels, and Eight Crazy Nights. For me, the movie often called the worst has been watched. That movie is known as Jack and Jill, and it isn’t a catchy fairy tale, it’s a disaster. Everything about it is horribly put together, from the cinematography, acting, editing, and directing by Dennis Dugan. If me and my brothers weren’t flipping through TV, then we wouldn’t have watched it, but here’s why we did.


Every weekend, we have trouble deciding what to watch late at night, a movie, TV show, or sporting event like Strongman. When we don’t resort to the WWE Network for an old pay-per-view, we just pick something and watch it. The TV was turned to Comedy Central (oh the irony), and Jack and Jill was a half hour in. We watched for a little bit, and here’s the kicker:

We couldn’t stop watching. It was so horrible that we couldn’t turn it off. Not in the way like movies such as The Room or Birdemic, but when you see a big budget movie from a major studio fail so spectacularly, you can’t help but just laugh at it. Other movies in this category include Epic Movie and Spawn. There are also terrible movies that provide almost no enjoyment like that, even though they are better made as movies, like Suicide Squad, Shark Night, and Little Fockers. Still, there are plenty of terrible movies out there that are probably worse than these.

41 year old
I have yet to see this one. I’m sure it’s a classic.

However, they can’t be that much worse than Jack and Jill. It features the eponymous twins, both played by Adam Sandler, and here’s my first issue with this movie. Being a twin myself, I always get a little annoyed when a piece of media just relies on the fact that twins are twins, and almost nothing else. I’m sure there are exceptions, but this movie is not one of them. Adam Sandler damn sure tried to obey that cliché, and he succeeded.


As Jill, he’s the typical annoying sibling from out of town visiting for the holidays. She lacks basic critical thinking skills and annoys everyone around her. Also, since it’s a bad comedy movie, she just has to be good at everything from jump rope to weight lifting. However, at least Sandler tries to be a different person there. As Jack, I don’t even think he’s trying. It comes off as he just wants to get through every scene as fast as possible so he just does the bare minimum to get it done. It’s as bland a performance as a performance can be.

The kid represents most people watching. I’m sure that’s been said before.

Speaking of bland, that’s exactly what Jack’s wife, played by Katie Holmes, is. She also does the bare minimum. There is little to no emotion in her performance. Her and Jack have two kids: an adopted son from India, and a daughter whose defining trait is that her and her doll always wear the same outfit.

The film proceeds with Jill trying to find a date, and she eventually ventures into online dating. When the date was at the door, Cory predicted that he was going to be played by Kevin Nealon. Instead, Norm Macdonald was on the other side of that door. He was one “Weekend Update” anchor off. Yeah, this movie features cameos and other roles from SNL Alumni, including Tim Meadows, Dana Carvey, and the aforementioned Macdonald. If you ever wanted to see David Spade in drag, this movie is for you. In addition, there are roles by Nick Swardson, Johnny Depp, and Dan Patrick of all people. The part that kind of confuses me is that in this universe, Sandler, Holmes, and Macdonald play characters but people like Johnny Depp and Al Pacino are playing themselves. Kind of odd.

Meanwhile, Jack, an advertising executive, is tasked with getting Al Pacino to appear in a commercial. Then, Jack and Jill go to a Lakers game that Pacino is at. I bet you can see where this is going.


Yep, Pacino falls for Jill. I’m not sure why, he just does. As bad as the writing in this movie is, Pacino tries his best to salvage it. His performance is easily the best part of the movie, because he’s actually emoting effectively. The movies progresses on with Jill and Pacino meeting up at the actor’s house. Jill leaves, and for some reason, she’s in the woods and she goes to a Mexican family’s reunion. Wikipedia states that the Mexican man is Jack’s gardener. I missed the first half hour so maybe they established that earlier. I’m not watching it to find out. Everything about this scene is horribly put together that words can’t do it justice. Just watch.

During this scene, we started laughing at how much this scene fails. So much so, that my older brother proclaimed:

“I’m at a loss for words!”

I couldn’t have said it better myself.

Then, some more shenanigans happen that I don’t even know why they happen, like Jill joining Jack’s family on a planned cruise, getting that Royal Caribbean product placement in. I actually went on a Royal Caribbean cruise a year after this movie was released, and they played this movie for a “Family Night,” which I skipped. I guess they had a deal.


To get him to do the commercial, Jack disguises himself as Jill to go to Pacino, whose so hell bent on getting with Jill that he agrees to take a helicopter to the cruise ship to pick Jack-in-disguise up. After Jill finds out, she leaves the cruise (somehow), and goes back home to NYC. She enters a restaurant that her and her late mother used to attend with a picture of her, and some bullies see her. You know, the bullies that are actually grown adults and therefore would never talk like they do? You’ve never seen those? Really?

jack and jill bullies

This surreal group is where David Spade’s deplorable cameo is seen. Through some trash talking, Jill proudly states that she hit it off with Pacino, then out of nowhere, Jack and his family show up. It’s not clear how much time passed between the cruise and this scene, so I’m assuming they got on a plane immediately after the cruise. Must be expensive.

To close this scene, Jill and Spade start fighting, and the twins start speaking gibberish to each other, like the movie just turned into The Sims. Again, this may have been shown earlier, but I’m never laying eyes on this movie again. The movie ends with Jill getting with Jack’s gardener, and Jack getting a commercial from Al Pacino. Would you like to see this commercial? It’s probably the best scene in the film, and it’s supposed to be bad. That’s how low the bar is for this movie. Here you go:

I usually keep an open mind before watching any movie. I was willing to believe that I would be able to laugh with the movie, like any comedy intends, at least once or twice. Besides maybe that ad, that never happened. We laughed at it. It fails as a comedy, a story, and a movie. The acting, directing, cinematography, and editing range from bland to grating. Suffice it to say, Jack and Jill is a strong contender for the title of “Worst Movie I’ve Ever Seen.”

MAC TWITTER: @M_American_C



Thanks for reading! YouTube clips uploaded by FunnyMovieClips and metnix1.

Author: Chase Edwards

I'm Chase and I just write about what interests me. Games, music, sports, and oddities are most likely to be my hot topics.

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