During its theatrical run last fall, the response to Adam Sandler’s cross-dressing comedy “Jack and Jill,” which made its DVD debut on Tuesday, was an overwhelming thumbs down: The film’s approval ratings on the website Rotten Tomatoes were 43 percent from audiences and an abysmal 3 percent from critics. The focus has mainly been on Sandler’s portrayal of a woman — in fact, his record-breaking sweep of Razzie nominations includes the distinction of Worst Actress — and upon the film’s recent U.K. release, The Guardian’s Steve Rose went so far as to write that his performance may represent “the death of the cross-dressing movie.”

Why does Sandler’s shtick fail to elicit laughter — or anything but a furrowed brow — and what might be the significance of his profound unfunniness for broader issues of gender and media?

In order for the humor in a film like this to take flight, the “ridiculous character” (aka, the guy who looks awkward in drag) needs to be played truthfully. As fellow thespian John C. Reilly says, it is the actor’s job “to tell the truth as much as you can,” and this honest commitment to exaggerated circumstances is what makes a scene funny.

But in “Jack and Jill,” Sandler seems too uncomfortable to play Jill’s truth and instead defensively scrambles to make derisive jokes about her. He emphasizes her rough and crass masculinity, rather than committing to revealing her (and his) true feminine qualities. One wonders why he would choose this material in the first place, if only to grab some laughs at the expense of unattractive women. The Guardian’s Rose suggests that perhaps underneath on-screen drag performances like Sandler’s “lie the unrequited yearnings of our fading comics to really get in touch with their big, fat feminine sides. It’s a shame none of them seems to have the balls.”

The fear of identifying with a person who is female or feminine is an oft-unspoken reality in Hollywood. The greatest actress of her generation, Meryl Streep, says heterosexual male actors and audiences have always been resistant to “assum[ing] a persona if that persona is a she.” But if this insidious fear — or “Femme Phobia,” as memoirist Julia Serano calls it — is the root cause of “Jack and Jill’s” bombastic failure, then the film industry has a real problem on its hands. Breaking the silence on this issue is crucial to averting flops like this in the future, as well as to uncovering the myriad ways in which Femme Phobia is harmful.

To begin with, what exactly is so terrifying to men about femininity? Numerous social scientific studies conclude that, for most men, there is a fear that presenting as too sensitive, too soft or too feminine may read as “gayness.” In simple terms, all things feminine in male behavior are considered to be “gay,” and all things “gay” are considered to be undesirable and bad and the worst possible thing for a man to be.

Perpetuating these attitudes on screen certainly exacerbates problems for LGBT communities, especially young people too often memorialized in a relentless news stream of bullying and harassment to the point of suicide or murder. But infrequently discussed in such news reports is the fact that such violence usually occurs due to people’s perceived sexuality based on gender presentation (i.e., men who are effeminate) as opposed to their stated sexuality (men openly identifying as gay).

What is talked about even less is the impact these attitudes have on straight men. In a 2010 piece for The Christian Science Monitor titled “Homophobia hurts straight men, too,” Jonathan Zimmerman emphasized how this contagious fear creates harmful limitations for straight men, like keeping them from having intimate, long-standing friendships with one another. This toxic fear seems to keep certain male actors, like Sandler, from maximizing their obvious creative potential. By widening the margins of their own gender expression, male actors would make room for more honest, effective and funnier work.

Not all straight male actors are so constrained, however, as evidenced by “Saturday Night Live” cast member Fred Armisen’s performance in IFC’s “Portlandia.” This sketch comedy series, which mocks hipster culture on the West/Left Coast, features Armisen in various roles, including several as women. Armisen’s performances are the polar opposite of Sandler’s: He fully embodies his female characters, honestly exposing his sensitive and feminine qualities — often to extremes — resulting in hilarity without mean-spiritedness, misogyny, homophobia or self-hatred. Armisen is authentically funny, and critics and audiences have embraced the show.

If more male actors allowed themselves to play a wider spectrum of gendered behaviors as Armisen does, the benefits would be subtle but substantial. This could reduce an epidemic male fear of seeming sensitive, feminine or gay. It might even contribute to a reduction in violence against all women and men, particularly those in the LGBT communities, as so often we behave, enact and are what we watch.

Your support matters…

Independent journalism is under threat and overshadowed by heavily funded mainstream media.

You can help level the playing field. Become a member.

Your tax-deductible contribution keeps us digging beneath the headlines to give you thought-provoking, investigative reporting and analysis that unearths what's really happening- without compromise.

Give today to support our courageous, independent journalists.