In 2011, Adam Sandler appeared in four films (five, if you count his uncredited cameo in the documentary Pearl Jam 20). Of these, Jack and Jill is probably the best remembered. Sandler appears as the titular Sadelstein twins in a dual role, with the mild-mannered Jack playing host to his irritating sister Jill for the holidays. The setup is nothing special but for one bizarre twist: Al Pacino plays a prominent role in the film—as himself.
Jack runs an advertising agency, where he works with the criminally underused Tim Meadows and Nick Swardson, both of whose only purpose in the film is apparently to feed a bored Sandler jokes. Dunkin' Donuts, we are told, is introducing a new beverage called the "Dunkaccino" and wants the agency to shoot a commercial with Al Pacino, because "Dunkaccino kind of sounds like" his name. It seems like a throwaway joke, but it is in fact the core around which the entire movie is constructed.
Most of the comedy in the film is meant to come from Jill's peculiar habits—she travels a pet cockatoo who bathes in chococlate—but the role is basically an excuse for Sandler to do drag and a goofy voice. Jack takes his sister to a Lakers game, where he hopes to meet Pacino and convince him to do the ad. Pacino falls for Jill, setting into motion a plot in which Jack attempts to convince the uninterested Jill to go out with the actor. When that fails, Jack instead dresses up as his sister and spends an evening with Pacino himself.
As a film, Jack and Jill exemplifies the kind of stuff Sandler was cranking out in the late aughts and early teens. It's all over the place tonally, pervaded by mean jokes that give way to a sappy, romcom-esque ending in the last twenty minutes. People appear for seemingly little reason other than to be in the film. The late Norm Macdonald is cast as "Funbucket," a man who takes Jill on a date and delivers zero jokes before escaping the situation by hiding from her on the bathroom ceiling. Subway spokesman and convicted child sex predator Jared Fogle is given a full minute of screen time. David Spade appears in drag in a single scene, getting into a physical altercation with Jill.
Product placement abounds. Jokes are used again and again. Two-thirds of the way through the movie, it becomes an ad for Royal Caribbean cruises. But the most bizarre aspect of Jack and Jill, and the reason for its enduring place in popular culture, is the very last scene: the ad Pacino shoots for Dunkin’.
It's a stunning thing, the Dunkaccino commercial—all the more so when you know it's coming and have sat through the entirety of Jack and Jill in advance of it. Pacino bursts into a Dunkin' Donuts, proclaiming that his name is now "Dunk" before launching into an intricately staged ’90s white-guy rap about the drink he's promoting, referencing his famous roles along the way. The bit has been floating around the internet since the movie was released, but truly found its audience with the @DailyDunkaccino Twitter account that launched in May 2020 and racked up nearly 50,000 followers posting user-submitted variations of the scene in the course of the following year. Poetically, the cashier who says "Dunkaccino?" in disbelief is played by Andy Goldenberg, who found fame as one of the first viral YouTubers by putting lyrics to well-known film theme songs.
Jack and Jill screens tonight, February 1, at Nitehawk Prospect Park in 35mm.
