Jack and Jill-2011

Director Dennis Dugan

Starring Adam Sandler

Scott’s Review #1,171

Reviewed August 16, 2021

Grade: F

Typically, an actor playing a dual role is a challenging and rewarding experience and can lead to accolades for a challenge well met.

While Adam Sandler may have been challenged, it’s the audience who suffers tremendously.

I can think of no redeeming qualities to mention during this review.

Anyone who watches Jack and Jill (2011) will ache for the duration of the running time, or scramble for the theater exit or pound the stop button on the remote.

Jack and Jill (2011) is the worst film Sandler has ever made, with a screeching over-the-top performance and terrible writing.

The additions of New York and Jewish stereotypes and every other stereotype in the book meant for laughs instead exude annoyance and disrespect.

To make matters worse, Al Pacino appears in a supporting role well beneath him and plays himself. And, to reach an assured low, the actor is forced to rap.

How embarrassing for him.

Poor Katie Holmes has little to do since she is trapped in the one-dimensional ‘wife role’.

Bad decision-making by writers, producers, and actors. Perhaps the makeup people enjoyed themselves.

The premise suggests the film could be hysterical, or at least partially amusing. Well-known actors dressing in drag and put in uncompromisingly awkward situations is nothing new and has been met with success.

Some Like It Hot (1959) and Tootsie (1982) are classics, resulting in kudos for Jack Lemmon, Tony Curtis, and Dustin Hoffman, respectively.

The main issue with Jack and Jill is that the writing stinks.

Never a fan of the Sandler-and-director-Dennis Dugan slapstick collaborations, I hope this drivel led to better acting choices for the actor.

He would later star in the superb Uncut Gems (2019) and miss out on an Oscar nomination by a whisker. I hope nobody saw Jack and Jill and revoked a vote for Sandler, though I couldn’t blame them if they did.

Let’s hope Sandler learned his lesson with this film. He must have, since his films vastly improved after this one.

Los Angeles advertising executive Jack (Adam Sandler) dreads the Thanksgiving holiday because his overbearing twin sister, Jill (also played by Sandler), makes her annual visit from New York City.

When Jack and his sister immediately butt heads, Jack feels guilty, and the only way to make it right is to invite her to stay through Hanukkah.

When actor Al Pacino (Al Pacino), whom Jack desperately needs to star in a commercial, becomes obsessed with Jill, Jack may be forced to extend his sister’s visit even longer to get what he wants.

Jack’s gardener, Felipe (Eugenio Derbez), also takes a shine to Jill.

Everything about the film is pretty bad but let’s point out the highlights…..or lowlights.

Sandler plays Jill as obnoxiously as possible and in a predictable form; Jack must disguise himself as Jill. Gee, I never saw that coming. Why any man, let alone two (Al and Felipe), would become enamored with her is beyond me.

Jack’s wife Erin (Holmes) and kids are as cookie-cutter as imaginable and possess every ‘neat and clean’ characteristic in the books. They are as white bread as wonder bread.

To match the stereotypes, why does Felipe have to be Mexican? It’s as if Dugan and Sandler (who co-wrote the screenplay) wanted every cliché imaginable.

Jill conquers Los Angeles with appearances on The Price Is Right, attendance at a Lakers game, and a cruise.

The film’s conclusion, after a myriad of expected misunderstandings between Jack and Jill and Jill and Al, ends with a silly New Year’s Eve high school reunion back in New York with classmates and bullies.

To confirm how bad Jack and Jill (2011) is at the 32nd Golden Raspberry Awards, it won all categories, a first in the thirty-two-year history of the annual parody event.

This is a film to be buried six feet under.