“It’s Not You, It’s the Chimichangas!” – Jill Sadelstein

After releasing a handful of lethargic comedies near the end of the 2000s, Adam Sandler and his production company, Happy Madison Productions, reached their lowest point in 2011 as Sandler was offered over £14 million to co-write and star in Jack and Jill. A rarely amusing, oddly boring and so gratingly sophomoric comedy that much of it plays with the same level of enjoyment as a high-pitched vocalist screeching into your ear. Packed with cringe-worthy jokes and overt product placement, in many ways, Jack and Jill feels like the result of Adam Sandler using an entire film to express just how cynical and contemptuous he has now become towards his famed comedy persona.

Plot Summary: Living his perfect life in Los Angeles with a beautiful wife and children, successful advertising executive, Jack Sadelstein, dreads only one thing each and every year; the Thanksgiving visit of his passive-aggressive twin sister, Jill. But, as Jack eagerly awaits for his sister to depart, renowned actor, Al Pacino, whom Jack desperately needs to star in a project, takes a shine to Jill, forcing Jack to reluctantly extend his sister’s visit…

Co-written by Steve Koren and Adam Sandler and directed by Dennis Dugan (Happy Gilmore, Big Daddy, I Now Pronounce You Chuck & Larry). The screenplay for Jack and Jill is often so leaden and formulaic that nearly any audience member will be able to predict where the story goes next as the film follows the typical plot of a dysfunctional family coming together with a sprinkling of pop culture references and numerous offensive gags parodying Indians, Mexicans and Jews, for good measure. Going off the film’s title, it’s also understandable that many would assume Jack and Jill has some kind of relation to the 18th-century nursery rhyme of the same name, which focuses on a boy named; Jack, and a girl named; Jill, as they embark on a journey to collect a pale of water. But, in actuality, the film has no relation to the nursery rhyme beyond its protagonist’s names, which begs the question; why is the film even called Jack and Jill aside from the simple use of alliteration?

In regard to the cast, Adam Sandler portrays Jack Sadelstein similar to how he portrays many of his characters, being a hassled family man whose needy, obnoxious twin sister, Jill, has come to stay for Thanksgiving and subsequently ruin his peaceful existence, once again portrayed by Sandler in profoundly unhilarious drag. What makes this worse, however, is that Sandler is at his most irritating when portraying Jill, raising his voice to be as annoying as possible and further fitting with her incredibly unlikeable characterisation, being idiotic and self-absorbed to an unbelievable degree. She’s an entirely overbearing character completely oblivious to social cues and seemingly has unresolved incestuous feelings for her brother, which is frequently played for laughs yet is an exceptionally strange choice on behalf of the screenwriters. Then there is Katie Holmes as Jack’s wholesome, good-natured wife, whose performance is dull and generic much like her character. And lastly, there is, of course, Al Pacino, who gives a shockingly committed performance, continually mocking himself and his lengthy career for the sake of a cheap gag.

Sadly, even legendary cinematographer Dean Cundey, who has worked on many iconic films from Back to the Future to Jurassic Park and Apollo 13, among many others, isn’t at his best here as the camerawork throughout Jack and Jill is relentlessly uninteresting, being nothing but mid-shot after mid-shot. Moreover, poor editing choices and terrible CG effects (of which there are a startling amount) are very frequent, distracting from much of the ‘comedy’ on-screen.

Placing most of the auditory focus on well-known songs such as I Got You Babe, Vacation and I’m a Believer, it’s easy to predict that the original score for Jack and Jill by Rupert Gregson-Williams and Waddy Wachtel isn’t very memorable. In fact, the score is barely even noticeable in the majority of the scenes it’s featured within.

If all of this wasn’t enough, Jack and Jill was actually the first film in Razzie history to win in every category in a single year, this included: Worst Picture, Worst Director, Worst Screenplay, Worst Actor, Worst Actress, Worst Supporting Actor, Worst Supporting Actress, Worst Screen Couple, Worst Screen Ensemble and even Worst Prequel, Remake, Rip-Off or Sequel as many believe that Jack and Jill is a rip-off of the exploitation-drama; Glen or Glenda from 1953. This record was previously held by the psychological horror; I Know Who Killed Me, with eight awards, including Worst Picture of 2007.

In summary, Jack and Jill is a truly unbearable comedy. With the exception of a few humorous moments and the genuinely charming interviews with real-life twins that bookend the film, this modern comedy has so little to offer it’s frankly impossible to recommend on any level. Still, undoubtedly, the most disappointing part of Jack and Jill is that only three years before its release, Adam Sandler headlined the delightful comedy-drama; Funny People, a film that actively poked fun at Sandler’s long list of appalling comedies. This led many to believe that Sandler was finished with these slothful releases once and for all, but evidently, this was far from the case. Rating: 2/10.