Plot: Jack (Adam Sandler) has a mind for the world of ads, but his latest task seems like a tall order even for his promotional skills. Dunkin’ Donuts wants to stay with Jack, but they need a big campaign and if he can’t deliver it, they will take their business to someone who can. While he has a keen ad sense, Dunkin’ Donuts wants Al Pacino in a commercial to promote their new Dunkaccino drink and of course, Jack can’t imagine a world where Pacino would agree to that. Meanwhile, his twin sister Jill (Adam Sandler) has just arrived to visit and while she loves her brother, he seems bothered to have to deal with her at all. After a series of clashes that him eager to see her return home, she manages to catch the attention of Pacino and by turn, Jack sees a chance to land the commercial of a lifetime. But can he put aside his bad attitude toward his sister or will it cost him his biggest account?
Entertainment Value: If there was a hall of fame for bad movies, Jack and Jill would be a first ballot contender. This is just an outlandish, mind boggling cinematic experience, the kind of movie that seems destined to be a cult classic, as it just throws every rule out the window. While most of Adam Sandler’s career is comedies that are more reunions for his friends than attempts at effective movies, Jack and Jill seems beamed from another planet, even by his standards of wackiness. The movie centers on Sandler playing twins and it is the laziest approach to this concept ever, with Sandler in a cheap wig and some minor makeup in the second role. But it is so ludicrous, it starts to work at times and the movie really goes for broke in chasing humor that is manic, terrible, and even fairly unpredictable, as it is often so random. Al Pacino’s presence alone makes this a must see, regardless of your taste for bad movies, but the slapdash writing, baffling sense of humor, and outright nonsensical elements ensure that for those who dine on terrible, outlandish cinema, Jack and Jill is a feast. This is a terrible movie, but it reaches peaks of awfulness few bad movies can even imagine, so to me, it earns its stripes as a bad movie hall of fame pick.
He might be one of the all time great actors, but Al Pacino can stink up the joint with the best of them. He has rattled off some outrageous performances in his career, chewing scenes and wringing scripts dry, but he channels pure madness here as a twisted take on his real life persona. As outlandish as his performance is in general, it is the Dunkaccino segment that rockets Jack and Jill past mortal bad movie into the stratosphere of jaw droppingly terrible. I love Pacino in this movie and his ridiculous presence has to be seen to be believed. Adam Sandler is his usual self here in one role, then just hams it up beyond belief as the twin sister. This is shrill, lazy, and just Sandler shouting all of his lines, a turn so horrible it becomes surreal at a certain point. Katie Holmes is in the middle of this nonsense and gives a warm, sincere performance, which is quite a contrast. The cast also includes David Spade, Nick Swardson, Eugenio Derbez, Tim Meadows, John McEnroe, Norm MacDonald, Shaq, Allen Covert, Dana Carvey, and of course, Subway’s Jared Fogel.