Jack Sadelstein (Adam Sandler), a successful advertising executive in Los Angeles with a beautiful wife (Katie Holmes) and kids, who dreads one event each year: the holiday visit of his identical twin sister Jill (also Adam Sandler). Jill’s neediness and passive-aggressiveness are maddening to Jack, turning his normally tranquil life upside down. Things spin even more out of control for Jack when Jill decides to extend her visit and he doesn’t think that she’ll ever leave!
Adam Sandler in drag: this is the gist of Jack and Jill, and Sandler doesn't skimp on the premise. He plays two roles, in fact: Jack is a successful L.A. TV producer, family man, and vaguely unpleasant shill for advertising clients. Jill is his sister, in town from the Bronx for a holiday visit. Obnoxious and passive-aggressive, she is also a lethal impersonation on Sandler's part, a wickedly exact send-up of the relative who never seems to get the hint. (One early dinner-table scene, where Jill refuses to acknowledge that the Christmas movie with Jimmy Stewart and the angel might in fact be It's a Wonderful Life, is a fine study in cluelessness.) Critics lambasted the film, emphasizing the ruthless physical humor and the gastrointestinal jokes, and to be sure, this is not Noel Coward territory (or even Moe Howard territory) we're in here. But the movie does have some surreal gags, and a large supporting role for Al Pacino, as himself (Jack is trying to convince Pacino to be a pitchman for a donut commercial). Pacino proves to be an awfully good sport about the whole thing, especially when his role requires him to fall for Jill in a variety of cockamamie ways. It may be more a series of sketches than an actual movie, but Jack and Jill does showcase Sandler's gift for outrageous impersonation–although admittedly, you'll probably have to be a die-hard Sandlerite to go the distance here. –Robert Horton