There’s a scene in JACK AND JILL where Jack Sadelstein (Adam Sandler) takes his family to the movies to see “Some Like It Hot.” It’s a nod to the classic cross-dressing comedy in which Tony Curtis and Jack Lemmon spend much of the film dressed as women.
Chewing the scenery the way an escaped pit bull chews the mailman's carotid (which, come to think of it, actually makes this a more subtle performance than the one in "88 Minutes"), Pacino falls for the unconventional Jill, resulting in some multi-layered drag shenanigans as Sandler-as-Jack impersonates Sandler-as-Jill, a development foreshadowed by the twins' viewing of "Some Like It Hot."
When it is funny, it's because it is done in a convincing way (think Dustin Hoffman in Tootsie), or in a way where the joke is that the supporting characters don't realize how unrealistic it looks (think Some Like It Hot).
Sandler the actor has never looked this apathetic, and the paycheck collecting is so obvious that the movie can’t even manage to sustain its own world, most blisteringly exposed by the ridiculous cameo appearance by cross-dressing classic Some Like it Hot.
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.
This is a major reason the in-no-way-funny Tootsie and Some Like it Hot are remembered as classics.