From the 1959 classic “Some Like It Hot” to the 1993 hit farce “Mrs. Doubtfire,” the man-in-drag routine has consistently provided surprisingly supple comic inspiration. A desperate man resorting to lipstick and a dress to avert a pending crisis is humorous enough; his inevitable transformation into a sensitive human being who better understands both himself and women is icing on the cake.

Given the success rate of this tried-and-true formula, one would think that its latest incarnation, the frat boy-in-a-dress comedy “Sorority Boys,” would teem with a giddy abundance of juicy hilarity. One would think that the frat boy, the epitome of pure, unbridled, beer-guzzling, female-objectifying machismo, would translate into the perfect vessel for pantyhose, pajama parties, and perfume.

One would be wrong. Under the unsteady direction of newcomer Wally Wolodarsky, “Sorority Boys” never capitalizes on its potential, trading inventive wit and personal exploration for tired sexual humor and uncomfortable gross-out gags.

Despite its comic failure, the film follows the superficial-male-gains-female-insight plot progression to a T. Dave (Barry Watson), Adam (Michael Rosenbaum), and Doofer (Harland Williams) are the social chairs of the fraternity K.O.K., a group that spends its time drinking, entrapping desirable sorority girls to add to its sexual conquests lists, and chucking vibrators through the windows of the more undesirable sorority, D.O.G.

When their brothers accuse them of stealing all the money for an important upcoming social event, the boys are banished from the house. Forced to pose as woman and join the D.O.G. sorority for free room and board while they attempt to prove their innocence, all three quickly realize the detrimental effects their abusive fraternity has on the insecure girls.

The film’s no-talent cast certainly contributes to its failure to execute a very promising scenario. The wonderful comic skill of Jack Lemmon and Robin Williams made their movies insightful, funny examinations of gender confusion. The male leads in “Sorority Boys” seem incapable of anything more than softening their voices and tripping in their high heels.

The writers come up with a few silly gags: Doofer’s, or “Roberta’s,” admission at a sorority meeting that he enjoys self-gratification and porn, and Adam’s obsession with his female imperfections. Only in these sparse moments do the writers seem aware of their comic context. Robert’s addiction to porn reveals desperate male horniness, yet it is only funny when stated in a room full of woman by a “woman.” Similarly, Adam’s vulnerable insecurity as a woman is funny in the context of his manipulation of this vulnerability as a man. These moments are simple, yet the genius of the man-in-drag concept is how it thrives off simplicity to create complexity.

Unfortunately, “Sorority Boys” mostly relies on today’s popular gross-out sex sequences to set its comic tone. Even worse, it takes this humor to uncomfortable extremes. In one truly cringe-worthy scene, Leah, the uptight president of D.O.G., joins her “sister” Dave in the shower, whose excitement is hidden by some well-placed bubbles. When she drops her washcloth, Dave, um, catches it, without using his hands. It is the perfect example of a sex joke without the “joke” or the “sex”, a desperate attempt to create an “American Pie”-like buzz that falls flat.

“Sorority Boys” fails because it follows the usually hilarious gender-switching premise without trusting the humor of that premise. It criticizes the often-hurtful extremes men can take to maintain their macho image. Yet in its attempt to show a transformation toward thoughtfulness and sensitivity, it uses humor that caters to the very infantile mentality it rejects.