Could Jack and Jill Earn Sandler Two Oscars?

You thought it wouldn’t happen. But then you saw the Jack and Jill trailer.

Adam Sandler has finally run out of ideas.

At least that’s what I thought. Stumped for any fresh comic characters to play as his naturally male self, he resorted to an old theatrical standby: dressing up in drag (as his needy, passive aggressive twin sister, Jill). Hijinks predictably ensue when Jill visits her brother, family man Jack (also played by Sandler) for the Thanksgiving holiday.

Surely it will be hilarious-- since Happy Gilmore, haven’t Sandler’s films only gotten funnier and funnier?

Will it be hilarious and heartwarming enough to finally earn Sandler the seat at the Academy Award contenders table he has long deserved? In fact, Jack and Jill might be the benchmark blockbuster that pries open a world of new Oscar possibilities. A single brilliant thespian taking home two awards for one film: Best Actor and Best Supporting Actor.

This retroactively calls to mind all the past two-timing actors who might have merited two times the gold statues if their films had proved Oscar-worthy. Like anyone who starred in a rendering of the The Parent Trap, an adaption of Dr. Jeckyll and Mr. Hyde, or Natalie Portman in her white/black swan ballet, Eddie Murphy in any Klumps sequel, Ed Norton in Leaves of Grass, Sally Field in Sybil, and the list goes on.

Yet rather than dwell on the past, why not look to the future? What other actors might amaze us by duplicating themselves as the opposite sex, fake boobs or prosthetic manhood and all? We’ve already seen Robin Williams’s Mrs. Doubtfire double, why not Pierce Brosnan? Nick Nolte would make an attractive women, no? Tilda Swinton would no doubt make a handsome man. We’re sure Robert Downey Jr. could pull off a double gender entendre.

Of course, this sort of double play also raises the question: Could double-Oscar winners demand double the salary? If that option existed would Hollywood unleash a rash of twin and alter-ego epics helmed by one star with an astronomical salary?

We’ll all just have to sit back and see what happens after Jack and Jill.