Aside from his award-winning performance in Uncut Gems and critically acclaimed roles in dramas such as Hustle, Adam Sandler has made some funny films. And though fans of Sandler are quick to point out such quotable-comedy classics as Happy Gilmore and The Waterboy, it’s true that most of his humor falls into a love-it-or-hate-it brand of silliness. His comedies may not be for everyone, but they certainly have earned a significant fan base. Knowing this, why was Jack And Jill so resoundingly and completely dismissed — even hated? In fact, it was so poorly received when first released, Jack and Jill actually set a record for Razzie awards, becoming the first movie to sweep every category.
MOVIEWEB VIDEO OF THE DAY
The truth is, it’s almost impossible to reverse course once negative sentiment around a movie gains momentum. And as a viewer, it’s not easy to watch with an open mind when the consensus is so negative. But here’s another truth: Jack and Jill is not only Sandler’s most underrated comedy, it may be his most sneaky-hilarious movie to date. Here are just a few of the subversively funny moments, scenes and characters from this overlooked comedic gem.
Al Pacino in the Role He Was Born to Play: Himself
Columbia Pictures
All by itself, the Al Pacino subplot in Jack And Jill is such absurdist gold that it makes this movie one the funniest Sandler has ever made. It’s no secret Pacino has been accused by critics of playing variations on the same character in many movies. By portraying an obsessive, bombastic, and over-the-top version of himself in Jack And Jill, Pacino is not only playing for the laughs, but also delivering a satirical commentary on the mythology surrounding one of the most celebrated actors in history. In fact, Elizabeth Weitzman wrote in the New York Daily News, saying Pacino “is downright hilarious and remarkably game as a wild-eyed version of himself.”
Whether he’s going ballistic on a theater audience for not silencing their phones, dancing and singing variations on his classic movie lines in a Dunkin’ Donuts commercial or crashing a New Year’s Eve party in full Don Quixote costume and character, Pacino-as-Pacino is wickedly funny throughout. In one of the most self-deprecating and knowingly funny moments, when Sandler (as Jill) apologizes for breaking an Oscar statue on Pacino’s bookcase during an impromptu stickball game and remarks that he must have others, Pacino simply shrugs and says, “You’d think it, but oddly enough, I don’t.”
Pacino’s inclusion goes well beyond a cameo, as he’s a fully realized character involved in the storyline. But speaking of cameo appearances, the dozens that pop up in Jack And Jill are an entirely different reason why this movie is so criminally overlooked.
Comedic Cameos: Shaq, Christie Brinkley, and Dozens More
Some play themselves, like Shaquille O’Neal as a spokeperson for a honey-baked ham or Regis Philbin wondering why he doesn’t have any good lines in a Pepto Bismol commercial. Others show up in character, like Dana Carvey as a Sesame Street puppeteer or David Spade as a mean girl from the Bronx. At a birthday party for Sandler’s Jack character, Dan Patrick, Christie Brinkley, Bill Romanowski, Michael Irvin, and countless infomercial spokespeople watch as John McEnroe gets in a screaming match with Nick Swardson over the existence of a higher being. And this is just the tip of the iceberg. Jack and Jill features Drew Carey hosting The Price is Right as Sandler’s Jill is knocked out cold by the show’s Big Wheel — and Caitlyn Jenner on stage in a theater production of Richard III.
All of these moments — from Sandler discussing bed-wetting with the “Shamwow Guy” to Johnny Depp courtside at a Lakers game — add an extra layer of bizarre humor to this underappreciated comedy. Another is the fleeting appearance by comic-great Norm Macdonald on a blind date with Jill.
Funbucket is Norm Macdonald at His Best
While his scene only lasts around three minutes, Norm Macdonald’s turn as online blind date “Funbucket” is a perfectly distilled version of the late comedian’s hilarious brand of dry, off-putting delivery. Macdonald, whose posthumous Netflix stand-up special was nominated for three Emmys, was a master of understated, matter-of-fact irreverence — with charmingly acerbic undertones. No strangers to one another, Macdonald and Sandler appeared together on Saturday Night Live as well as in Sandler’s Grown Ups, Billy Madison and Jack And Jill. In addition to several movies and TV shows, Macdonald also lent his voice to many films, most notably as the dog Lucky in three Doctor Doolittle movies. His quick appearance as Funbucket in Jack And Jill is one of his briefest roles, but it is a perfect example of why the late comedian remains one of the most revered and beloved of his generation.
Eugenio Derbez Stealing Scenes Before He Was a Star
Eugenio Derbez hit a box office home run in 2013 as the writer, director, and star of Instructions Not Included, which became the highest-grossing Spanish-language film in North American history at the time. The premise of a playboy who must grow up quickly when a former girlfriend leaves him with their child to raise sounds like a well-worn comedy trope, but Instructions Not Included was a heartfelt movie with just enough laughs to add levity to a story about the deep bond between a single parent and their child — and the drama when that relationship is threatened. Though today Derbez is a star in his own right — appearing in How To Be A Latin Lover (2017), Overboard (2018) and Hulu’s The Valet — his scenes as Felipe (and Felipe’s grandmother) in Jack And Jill put his charismatic comedy chops on full display. It’s also not the only time Derbez and Sandler worked together, as the two both appeared in Netflix’s Sandy Wexler in 2017.
While people and critics either love or hate Sandler’s comedies, their hatred of Jack And Jill seemed unanimous. Sandler has evolved throughout his career and always taken roles to stretch his range, from Spanglish and Funny People to Punch Drunk Love. But there is a part of him that will always seem most at home when he’s playing the room for laughs, even while accepting the Performer Tribute Award at the Gotham Awards. Jack and Jill was by no means a perfect movie, but it’s beyond undervalued as a comedy coming from one of the most successful in the game, with decades of laughs to show for his efforts. Whether it’s Pacino rap-singing lines from The Godfather as he sells a blended chocolate breakfast drink or the surreal running gag where Sandler’s son scotch-tapes things to his body, Jack and Jill is not only the most underrated Adam Sandler comedy, it may just be his funniest.
