Jack and Jill Trailer Starts a Trend: Sean Penn and Sherlock Holmes Get In on Adam Sandler’s Cross-Dressing Action


While George C. Scott might beg to differ, the trailer for Jack and Jill, Adam Sandler’s latest high-concept excuse for him to hang out with his buddies farce has confirmed what we’ve long suspected: Comic cross-dressing is back, baby! Sure, none of the other contenders appear to reach the awesomeful heights (or lows) of Sandler’s Linda Richman: The Movie, but they certainly suggest a transv— er, trend.

First up is the trailer for Sherlock Holmes: A Game of Shadows (above), in which a lipsticked Robert Downey Jr., having already conquered kung-fu, Rachel McAdams, and the homoerotic hearts of Jude Law slash-fic authors everywhere, now attempts to solve crimes using his own tightly bodiced body. Also, just last week it was announced that Glenn Close would attempt to position herself as the “not Meryl Streep” candidate at next year’s Oscars by starring in Albert Nobbs, a cross-dressing fable about a woman who pretends to be a butler in 19th century Dublin. (The L.A. Times describes it as “a sort of Irish Yentl,” which we sincerely hope they’ll consider putting on the poster.)


And finally there’s the bizarro This Must Be the Place in which Sean Penn — playing an aging, Robert Smith-type rocker — consults with Judd Hirsch (!) in order to track down his Holocaust-surviving father’s Nazi persecutor (!!), a plot that we’d still be scratching our heads over if we weren’t so distracted by Penn’s cherry-red painted lips, his smoky eyeliner, his craggy, terrifying worry lines … Gah! Sorry.

Anyway, drag fans, time to put away your Tootsie DVDs and lower the volume (but not the fabulousness) on your RuPaul records. It’s a new golden (earring)-age of cross-dressing in Hollywood and we know we’re not alone when we say: What’s Jamie Farr up to these days, anyway?

Filed Under: Adam Sandler, Glenn Close, Jack and Jill, Movies, Scouting Report, Sean Penn, Trailers

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Andy Greenwald is a staff writer for Grantland.

Archive @ andygreenwald