Skip to main content

Adam Sandler (far left) and Adam Sandler (far right) star in "Jack and Jill".


1 out of 4 stars


A marathon of Tyler Perry's Madea flicks is preferable to Jack and Jill, a noxious PG comedy starring Adam Sandler as a pair of middle-aged male-female twins that should have been separated at birth to spare us from this movie.

Men in drag are a tried-and-true staple of film comedy. It's generally funniest when a male actor plays a man disguising himself as a woman for an important plot purpose à la Tony Curtis and Jack Lemmon in Some Like it Hot, Dustin Hoffman in Tootsie and Robin Williams in Mrs. Doubtfire.

In those movies the laughs come from the transformation pains (hair removal, undergarment fittings), slip-ups and the character's reaction to living in a woman's world (thwarting male advances, etc.). This scenario actually does happen towards the end of Jack and Jill but it's cruel and creepy, not funny.

Story continues below advertisement

Sandler plays a woman – Jill, an athletic chatterbox spinster who lives in the Bronx – and also acts opposite himself as Jack, a successful L.A. ad exec with a wife (Katie Holmes) and two kids. Even with modern advances in makeup and special effects, both are tricky feats for any actor and Sandler – who has a hard time wiping that hint of a smirk off his face in most of his screen roles – falls short of meeting the challenge.

Aside from the painful experience of watching Sandler in a bad wig and loud woman's clothing and using a voice that is disturbingly reminiscent of Roger Rabbit, Jack and Jill has an unfathomably bizarre story. And it revolves around a performance by Al Pacino in one of the strangest "actor playing himself" roles in Hollywood history.

After Jill lands at Jack's family home for her annual Thanksgiving visit (with her entire wardrobe and pet cockatoo Poopsie), her twin brother can barely keep his loathing in check. He may be mean, but he's just saying what we're thinking. She manages to guilt Jack into allowing her to stay through to Christmas, but he decides Jill needs a man in her life.

After internet match-making fails, Jack takes Jill to a Lakers game where Al Pacino (currently tearing up the scenery in a local production of Richard III) takes more than a shining to this large buxom gal from the Bronx. She's the key, inexplicably, for Pacino to find a lost part of his soul he needs in order to accept the role of Don Quixote in a Broadway production of the musical Man of la Mancha.

This is potentially a lucky break for Jack, who's been working up the nerve to approach Pacino to participate in an ad campaign for Dunkin Donuts. But Jill, whom Pacino takes back to his place, is weirded out by the actor's aggressive needy behaviour and wants nothing more to do with him. Can you see it coming? Yes indeed, Jack eventually comes to the point where he must disguise himself as his sister to get Pacino on board.

Unlike the aforementioned "man in drag" movies, there is little situational humour in Jack and Jill. Instead, Sandler, co-writer Steve Koren and favoured Sandler director Dennis Duggan go for the gags, with the homeless, old people and ethnic minorities the butt of some jokes.

The most entertaining part of Jack and Jill is actually the little documentary that rolls during the end credits, where various pairs of real-life identical and fraternal twins banter about their relationships. But this is hardly enough reason to sit through a double dose of Sandler in a cheerless holiday comedy.

Story continues below advertisement

Special to The Globe and Mail

Jack and Jill

  • Directed by Dennis Duggan
  • Written by Steve Koren and Ben Zook
  • Starring Adam Sandler, Katie Holmes, Eugenio Derbez, Al Pacino, Nick Swardson, Tim Meadows and Norm MacDonald
  • Classification: PG
Report an error
Comments are closed

We have closed comments on this story for legal reasons. For more information on our commenting policies and how our community-based moderation works, please read our Community Guidelines and our Terms and Conditions.