10 Worst Movies Involving Men Dressed As Women

Every year, thousands of young girls move to Los Angeles and New York with the dream of becoming the next Hollywood starlet. There's no shortage of women to play the female roles, so why are there still so many men dressing up as women in the movies? In Shakespeare's time, it was customary for plays to be men-only productions, bringing about the need for some cross-dressing roles. Now though, the gimmick is becoming a bit of a drag. These 10 movies will make you long for the days when comedies were full of original ideas and men were men.

  1. Jack and Jill

    After taking on some more serious roles in movies like Funny People and Punch-Drunk Love, Adam Sandler went back to his old ways and proved once again why we shouldn't expect too much from him. In his newest movie, Jack and Jill, Sandler plays a cynical man and his annoying twin sister. The male Sandler character, who uses the normal annoying Sandler voice, is supposed to learn something about family while the female Sandler, with a higher-pitched annoying Sandler voice, gets frisky with Al Pacino. Critics and audiences have agreed that this movie is a flop, especially since one Sandler is almost too much to handle in a movie.

  2. White Chicks

    Basically any movie where people have to wear prosthetic faces to change gender and races is a bad idea. Add the Wayan brothers to the mix, and it's one of the worst movies ever made. White Chicks follows two FBI agents who are tasked with protecting a pair of rich sisters. Of course, something goes wrong and they think the best option is to pretend to be the girls themselves. They become the strangest-looking white girls you'll ever see, and somehow everyone in the girls' lives is oblivious to the fact that the girls are taller, uglier, and talk differently than before. The film scored a painful 15% rating on Rotten Tomatoes.

  3. Diary of a Mad Black Woman

    Even though there are plenty of sassy old ladies out there to play the part of Madea in this and many other Tyler Perry productions, Perry apparently thought it best to take on the role himself. That was a mistake. The movie without Madea is a soul-touching drama about a woman whose husband cheats on her and forces her to move out and the anger she deals with as a result. Madea is straight out of a Saturday Night Live sketch, except not as funny. Perry's character (well, one of them) destroys the movie, making it unbalanced and hard to watch.

  4. To Wong Foo, Thanks for Everything! Julie Newmar

    This movie may be worth watching just to see Patrick Swayze and Wesley Snipes in drag, but the actual storyline leaves something to be desired. We're again left wondering how movie producers expect us to believe that a whole town would be fooled into thinking these drag queens are women. Sure, Swayze's not the worst woman we've ever seen, but it wouldn't take long to figure out he's actually a man in a dress. Three drag queens from New York take a road trip to L.A., but get stopped in a small town where they teach the people there lessons about life. Though it could've been a powerful message about small-town views on transvestites, it's just silly, with makeovers for all and a strawberry festival.

  5. Sorority Boys

    You would think that Hollywood would eventually begin to catch on to the fact that the guys-dressed-as-girls gimmick is only funny for the length of a trailer (if that), but they just keep churning out the full-length drag flicks. Sorority Boys aimed for the lowest common denominator of humor, with a fraternity called KOK and sorority named DOG, and played on the ever-popular college theme. Three guys are kicked out of their fraternity after being wrongly accused of a crime, and to clear their names, they have to dress like girls and live in the DOG sorority house. The movie is exactly what you would expect, with a couple of romantic subplots made awkward by the gender confusion and plenty of dumb jokes about genitalia.

  6. Nutty Professor II: The Klumps

    Maybe the producers were worried that the Klumps, the family of the main character of The Nutty Professor, wouldn't look enough alike to be a believable family. The obvious solution was to have Eddie Murphy play all of the characters, including the women. In appearance, Murphy makes a decent female, but as soon as he opens his mouth, it's obvious there are multiple Murphys in most scenes. In fact, he plays eight of the characters, including a skinny Murphy who makes out with the granny version of himself. If that doesn't speak volumes about the quality of this film, nothing will. The nutty professor creates a youth formula, separates his jerk DNA from his normal nice-guy DNA, and problems follow. The jokes are basic, the plot is ridiculous, and you'll never want to see Murphy again in your life.

  7. Ladybugs

    Luckily for everyone involved, Rodney Dangerfield does not spend the whole movie dressed in drag. Unluckily, though, Dangerfield is still the star of this terrible soccer comedy. His character takes on the task of coaching a girls soccer team in order to receive a promotion at his job, a stupid idea since he knows nothing about the sport and the team members know even less. Dangerfield dresses a boy up like a girl so that their team can win, because everyone knows boys are better at everything. Dangerfield does dabble in drag, though, when he pretends to be the boy/girl's mother, and as you'd imagine, he is not a pretty lady.

  8. Big Mommas

    Like Father, Like Son: This is the third movie in the Big Momma franchise, and it's amazing this film was even created. Martin Lawrence stars in this film, using the tired gag he used in the two previous movies — dressing like a fat lady. This time he involves his character's son, as well, dressing him like a woman and enrolling him in an all-girls school so they can solve a crime or something ridiculous. Though we hope to never meet them, there is obviously an audience somewhere that believes that a bulky man would fit in at a school full of tiny-framed girls and that a man would be attracted to Lawrence in a fat suit.

  9. Glen or Glenda

    Often hailed as one of the worst films ever produced, Glen or Glenda has gained a cult following for being so terrible. It follows a man named Glen, played by director and writer Ed Wood, who himself is said to have enjoyed wearing women's clothing. Glen longs to wear women's clothing, and eventually finds acceptance from his wife, who gives him her beautiful angora sweater. Most of the film is just strange, and it's obvious it was filmed on a tight budget. Even though Wood wanted to make a serious movie about cross-dressing and sex change operations, he ended up leaving audiences more confused than his main character.

  10. Hairspray

    The latest movie based on the musical, Hairspray, is supposed to be a little bit corny (one of the characters' names is Corny, after all), but the camp value would be enough without the added oddity of John Travolta dressed as a big-boned woman. It's a far cry from his Grease and Saturday Night Fever days, that's for sure. The role has always been played by men in drag, on Broadway and on the big screen, but it does nothing for this movie with a message. Afterward, you'll probably be tapping your feet to the music and believing that big girls are beautiful, but you won't be able to get the image of John Travolta and Christopher Walken out of your head.