Jill (Sandler), an awkward, boisterous 43 year-old single woman, visits her twin brother, Jack (also played by Sandler), for the holidays. Jack has always had difficulties with his loud-mouthed sister, but through a series of events, which include a love struck Al Pacino, as himself, and Jill’s budding romance with a Latino landscaper, Jack must come to terms with his deep seeded connection to his twin.
What makes Jack and Jill so unfunny?
It has a laundry list of comedic actors who show up in cameos or small supporting roles, including Nick Swardson, David Spade, Norm MacDonald, Dana Carvey, Tim Meadows, and Allen Covert. Though most have seen their glory days, none of them is utterly devoid of talent.
Jack and Jill employs the tired, yet not always unfunny, gimmick of a man dressing as a woman, and here we get to part of the problem.
Because Jill, as a character, is actually a woman, the audience gets all of the awkwardness of Sandler playing an ugly woman, without the potentially funny, farcical comedy that would come from an onscreen male character playing a woman. There is one short scene where Jack impersonates Jill towards the end, but it’s just not worth the setup for so small a payoff.
In addition, because Sandler had to shoot his scenes twice, once as each character, the scenes lose the energy that would have come with throwing dialogue around between two actors. Things must stay perfectly scripted, and light-hearted improvisation, which can save a silly, gimmick driven comedy, has to be avoided for the sake of Sandler’s costume change.
I kept wondering why Jill had to be a twin and not just sister, and why Sandler had to play both parts. Had they cast a capable actress opposite Sandler, they would have at least allowed for some off-script banter. Instead we get Katie Holmes, one of the most boring actresses alive, as Jack’s wife.
The way that Jack and Jill was funded also stifles its narrative opportunities. Both Dunkin’ Donuts and Royal Caribbean International coughed up tons of money to make the movie possible. Both brands are paraded through the motion picture, which makes Jack and Jill feel more like a 90 minute promotional video than a movie.
The worst part of this whole endeavor is that the movie is utterly mediocre, and never so-bad-it’s-funny. It might have been silly fun, many of Sandler’s previous films have been laugh inducing guilty pleasures, but Jack and Jill will just have you pondering how it all went so wrong.
At the end of Jack and Jill, Pacino, having just acted in a terrible Dunkin Donuts advertisement, asks Jack to burn all of the copies of the commercial. No one must ever see it.
I wonder how he felt about Jack and Jill.