Celebrity Gender-Benders: Who Crossed The Line Successfully—And Who Didn't

Photo: United Artists/ Roadside/ 20th Century Fox

Sometimes the best way to get recognition is to play against type. And that is exactly what this list of 17 gender-bending actors and actresses did—for better or worse.

This weekend, Adam Sandler received a record breaking 11 Razzie nominations for his three terrible movies this year. One in particular, “Jack and Jill” earned him the disgrace of getting Worst Actor and Worst Actress.

Glenn Close, however, received an Oscar nod for this year’s “Albert Nobbs,” in which she plays a woman disguising herself as a male butler.

In honour of Sandler’s horrific display of comedic talent and Close’s cross-dressing brush with Oscar, we’ve compiled the best and worst gender-bending performances on screen from the past 50 years.

The same year that Adam Sandler offered up a terrible cross-dressing performance in 'Jack&Jill,' Glenn Close delivered one that received an Oscar nomination.

Close plays Albert Nobbs, a woman who has disguised herself as a man for 30 years in order to serve as a butler and save up money for her own shop.

The actress received her sixth Oscar nomination for the role while the film was also nominated for Best Makeup (rightfully so) and Best Supporting Actress for Janet McTeer who also expertly plays a woman who disguises herself as a man.

Following in the footsteps of Eddie Murphy's disgustingly bad 'Norbit,' Adam Sandler tackles cross dressing in this film about a man who must spend Thanksgiving with his awful twin sister, who then refuses to leave his house and family.

If screeching like a hyena were a talent, Sandler would win an Oscar for it in this film. His 'Jill' is an absolute disaster who actually attracts the advances of Al Pacino, playing himself as a total creep.

It's no wonder Sandler was nominated for Worst Actor and Actress.

The film also had the dishonor of cleaning up with Razzie nominations including a Worst Supporting Actress nod for Katie Holmes (as Sandler's wife), two Worst Supporting Actor nods for Pacino and Sandler movie staple Nick Swarsdon, Worst Screenplay, Worst Director and Worst Picture, just to name a few.

Another man-becomes-woman film, this movie works solely on the comedic talent of Robin Williams.

'Mrs. Doubtfire' is a sweet film about a man who loses his family and must dress as a female housekeeper to get close to them again.

Williams shines as Mrs. Doubtfire and as his male self Daniel Hillard. His affinity for impressions, voices and physical comedy make this film a must-see for all audiences.

Check out Williams doing his, or well, 'her,' thing:

The fact that there are three of these films is mind boggling.

Martin Lawrence stars as an FBI agent who goes undercover as an old lady to protect a federal witness and her son from those she must testify against.

Imagine Eddie Murphy in 'The Nutty Professor' but much much worse.

And to make matters worse, 'Tropic Thunder' actor Brandon T. Jackson joined Lawrence for the third film as Lawrence's son who also dons the woman getup.

Check out the third film's trailer here.

Iconic actors Tony Curtis and Jack Lemmon donned female garb to hide out from mobsters and play in an all-female band in this classic comedy.

The two then fall head over heels for their lead singer, the one and only Marilyn Monroe, leading to all sorts of hilarious hijinks and complications.

The pair are ridiculously funny here as women, especially when Lemmon's character Daphne is courted by a millionaire.

Eddie Murphy has played a woman before, but this time he stepped over the line of awful.

Murphy pulls double and triple duty playing pretty much every character in this film about a schmuck who is in an abusive relationship with a massively evil woman.

The film was nominated for eight Razzies with Murphy winning Worst Actor, Worst Supporting Actor and Worst Supporting Actress.

An adaptation of the Broadway play 'La Cage Au Folles,' this film stars Nathan Lane and Robin Williams as two gay men who find out their son wants to get married... to a woman... with a Republican family.

In order to impress the family, Lane takes on the role of their son's mother from head to toe.

The film is full of laughs with Williams and Lane playing wonderfully off of each other.

Another obvious, ridiculous concept, 'Juwanna Mann' is about a popular basketball player who gets banned from the NBA and must dress as a woman to keep playing ball.

Nuñes is over-the-top and awful. But more than that, the film is comically bad.

Gwyneth Paltrow won an Oscar for playing Viola, a daughter of a wealthy merchant who must dress as a man to act in William Shakespeare's plays.

Viola falls in love with Shakespeare and must continue to keep her true identity unknown to the others in the play because it was illegal for women to act in the theatre.

There's a reason Paltrow won the Oscar here- she's just brilliant.

In yet another instalment of bad Wayans' films, brother Shawn and Marlon Wayans play two FBI agents who must pose as the witnesses they are tasked to protect.

They just so happen to be women... who are white.

That's the long and short of the film that has been called 'banshee-howlingly awful.'

After playing such joyful roles as Mary Poppins and Maria from 'The Sound of Music,' it was high time for Julie Andrews to play someone with a little more controversy.

The iconic actress has a ball in this film which follows a young woman who dresses as a man to play a female impersonator. Got that? Good because that's just the beginning.

Andrews' performance was a massive hit, leading her to receive her third Oscar nomination for Best Actress.

World War II films are usually must-sees.

But not this one.

'Friends' star Matt LeBlanc plays an American soldier who must go undercover as a woman in Germany to get secrets about the Nazi's invasion plans.

And that's all you really need to know about this awful plot.

When Dave, Doofer and Adam get kicked out of their homes, they must find new, cheap housing.

So what is their brilliant plan?

Dress up as women and live in a sorority house of course.

The three actors here are awful and play up the ridiculous stereotypes about women. It's just plain dumb.

'Desperate Housewives' star Felicity Huffman turned heads when she played a transsexual woman Bree Osbourne who is in the final stages before getting a sex change operation.

Before she can become a woman, she must reconnect with a son she never she had on a long road trip that is riddled with crazy hijinks.

Huffman was lauded for her fantastic performance playing a man who wants to become a woman. She was even nominated for a Best Actress Oscar and won Best Actress in a Drama at the Golden Globes.

While technically Tim Curry's character is a transvestite, the character is just too good to pass up.

Curry brilliantly plays the villainous Frank-N-Furter; he's determined to create the perfect man, Rocky Horror.

The film is a cult phenomenon and audiences everywhere dress up as Frank to watch midnight viewings of Brad, Janet, Rocky, and all of the other kooky characters from 'The Rocky Horror Picture Show.'

In another controversial turn, 'Batman Begins' star Cillian Murphy plays Patrick 'Kitten' Braden, a young transgendered man in 1970s who unknowingly stumbles across dangerous IRA activities in London on his search to find his mother.

Murphy's brilliant performance won rave reviews and helped the actor score a Golden Globe nomination for Best Actor.

A delightfully corny and charming comedy, 'Tootsie' has the same formula as most gender bending films.

Dustin Hoffman's character Michael Dorsey is a struggling actor who can't find work because of he is 'difficult to work with.' So Dorsey takes drastic action by cross dressing and landing a role on a hit soap opera.

Predictably, he falls in love and men fall in love with his female alter-ego, but Hoffman's quirky and sweet performance and the great writing make this film an American classic.

In fact, Hoffman scored his fifth Oscar nomination for the role.

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