After all - as Dustin Hoffman did so memorably with Tootsie - there's still a point to be made about the roles available to women in film and television, right?
Alas, "Jack and Jill" is more " Norbit " than "Tootsie" or "Mrs.
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).
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.
Picture "Tootsie" if everyone in the cast had a head injury.