White Male Actors Who Wore Dresses In Movies?

Tyler Perry, Eddie Murphy, Martin Lawrence, Jamie Foxx, Kenan Thompson, and Tyler Perry are among the many memorable male actors who have worn skirts, dresses, or kilts on the red carpet. In Casablanca, Rick Blaine, played by Humphrey Bogart in the 1942 movie, wears white with all the charm ever contained in a single suit. Michael Fassbenders deleted drag turn in X-Men: First Class got us thinking of the many memorable male actors who’ve spent some time in the women’s world.

At the 91st Academy Awards in Los Angeles, Billy Porter shut down the Met Gala red carpet when he arrived on a litter—carried by six shirtless men! The film Some Like It Hot features two struggling musicians having to dress as women to escape the ire of gangsters. In Blake Edwards’ 1982 musical comedy, Brad Pitt turned heads when he arrived at the Bullet Train screening in Berlin in a brown skirt that showed off his many leg tattoos.

The man-dressed-as-woman trope is older than all of our ages put together, but if you’re theory is correct, there’s a comic that shits on the whole theory. The key to this is that in mainstream movies, a guy in drag is usually meant to be funny.

In summary, many white male actors have worn dresses in movies and TV shows, with some even displaying their choice of fashion.


📹 White actors wearing dresses like a PUNK for Hollywood #foryou #clubshayshay #diddy #fyp


Who dresses actors in movies?

Costume designers design, create and hire the costumes for the cast. They start by working with directors, producers, writers, the production designer and hair and makeup designer to contribute to the look and storytelling of the production. They research, sketch and draw mood boards of characters and clothes to communicate the style.

They then break down the script, working out what they need to create or hire. Working within tight budgets and deadlines, they recruit a team, organise a schedule of purchases and ensure the costumes are created on time for fittings. With the help of the team they schedule fittings and take photographs. These are then discussed with the producer and director and signed off.

Once shooting starts, they are always on set whenever there are new actors or new looks.

Who are the black cross dressing actors?
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Who are the black cross dressing actors?

Male comedians appearing in drag seemingly has universal appeal that cuts across cultural lines. Eddie Murphy, Martin Lawrence, Jamie Foxx, Kenan Thompson of “Saturday Night Live” and Tyler Perry are among the African American performers who have generated laughs by cross-dressing.

But despite the popularity of Perrys gun-toting, insult-hurling Madea, Lawrences turns as Sheneneh on his sitcom “Martin” and the cranky title character in “Big Mommas House” and the various women Murphy has played in “The Nutty Professor” films and “Norbit,” some observers inside and outside African American creative circles say the sight of black male performers in drag also carries troubling cultural baggage. They contend the caricatures are no laughing matter and jeopardize the image of African American masculinity.

Todd Boyd, a professor of critical studies at USCs School of Cinematic Arts, said the roles “humiliate and emasculate black men — it renders them less than powerful.”

Who is the male transvestite comedian?
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Who is the male transvestite comedian?

Eddie Izzard is a stand-up comedian, actor, writer and political activist known for his straight transvestite cross-dressing both on- and off-stage, and an act typified by whimsical flights of fancy.

E7 – Eddie Izzard, Jon Favreau, Seann Walsh, Romesh Ranganathan, Shawn Mendes;

  • Special – Monty Python Live: Backstage
  • Special – Monty Python Live: One Down, Five To Go

E5 – David Attenborough, Eddie Izzard, Russell Brand, Dolph Lundgren, Pulp;

Who was the black actor dressed as a woman?
(Image Source: Pixabay.com)

Who was the black actor dressed as a woman?

Martin Lawrence dressed up as a woman in the movie Big Mommas House and on the TV show Martin as Sheneneh.

Tyler Perry dresses up as a women in all of the Madea movies.

Jamie Foxx dressed up as a woman on the 90s TV show In Living Color.

Who is the guy in 27 Dresses?
(Image Source: Pixabay.com)

Who is the guy in 27 Dresses?

27 Dresses is a 2008 American romantic comedy film directed by Anne Fletcher, written by Aline Brosh McKenna, and starring Katherine Heigl and James Marsden. The film was released in the United States on January 18, 2008. It received mixed reviews from critics and grossed $162.7 million against its $30 million budget.

Plotedit. Jane Nichols has been a bridesmaid for twenty-seven weddings. One night, while she is attending two weddings almost simultaneously, she meets Kevin Doyle, who disgusts her with his cynical views of marriage. Kevin and Jane share a cab home, where she forgets her day planner. Kevin snoops through the planner and resolves to return it to Jane. Meanwhile, Janes sister Tess returns from a trip to Europe and quickly falls in love with Janes boss George, on whom Jane has an unrequited crush. Tess feigns interest in Georges passion for the outdoors and animal rights, and their courtship progresses rapidly. Soon, they announce plans to marry in only three weeks. Tess enlists Jane to be the wedding planner.

Tess and Georges nuptials will be featured in the newspapers Commitments section. The reporter turns out to be Kevin, who writes wedding announcements under the pseudonym Malcolm. Kevin successfully returns Janes planner but decides to use the contents as material for a piece on the perennial bridesmaid as a stepping stone to more serious journalistic pursuits. Jane is unaware of Kevins intentions. During their interview about Tesss wedding, Jane shows him the 27 bridesmaids dresses in her closet. He takes pictures of her wearing all 27 dresses and submits the photos and his article about Jane for publication. As Kevin and Jane grow closer, he has second thoughts and begs his editor to hold off on publishing the article.

Are there any inappropriate scenes in 27 Dresses?
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Are there any inappropriate scenes in 27 Dresses?

Nudity and sexual activity. There is some nudity and sexual activity in this movie, including:

  • Jane and Kevin begin kissing passionately in the car.The suggestion is clearly that they have sex, but no graphic details are shown.
  • Several segments early in the film where Jane is changing clothes in the back of a taxi.Viewers see the occasional bare leg and back, etc, but such nudity is implied, rather than overt.

Coarse language. There is some coarse language in this movie, including: boobs, asshole, bitch, what the hell and Oh God.

Ideas to discuss with your children. 27 Dresses is an enjoyable romantic comedy directed by Anne Fletcher.This film is pitched at young females aged over 12, but may also be entertaining to older audiences.

Who was the first actor to cross-dress?
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Who was the first actor to cross-dress?

Cross-dressing in motion pictures began in the early days of the silent films. Charlie Chaplin and Stan Laurel brought the tradition of female impersonation in the English music halls when they came to America with Fred Karnos comedy troupe in 1910. Both Chaplin and Laurel occasionally dressed as women in their films. Even the beefy American actor Wallace Beery appeared in a series of silent films as a Swedish woman. The Three Stooges, especially Curly (Jerry Howard), sometimes appeared in drag in their short films. The tradition has continued for many years, usually played for laughs. Only in recent decades have there been dramatic films in which cross-dressing was included, possibly because of strict censorship of American films until the mid-1960s.

Cross-gender acting, on the other hand, refers to actors or actresses portraying a character of the opposite gender.

Catalina de Erauso (1592–1650), known as la monja alférez the Nun Lieutenant, was a Spanish woman who, after being sent to a convent at the age of 4, escaped from it disguised as a man, fled to America and enrolled herself in the Spanish army under the false name of Alonso Díaz Ramírez de Guzmán.16 She served under several captains, including her own brother, and was never discovered. She was said to behave as an extremely cruel soldier, although she had a successful career, reaching the rank of alférez (lieutenant) and becoming quite well known in the Americas. After a fight in which she killed a man, she was severely injured, and fearing her end, she confessed her true sex to a bishop. She nonetheless survived, and there was a huge scandal afterwards, especially since as a man she had become quite famous in the Americas, and because nobody had ever suspected anything about her true sex. Nevertheless, thanks to the scandal and her fame as a brave soldier, she became a celebrity. She went back to Spain, and was even granted a special dispensation by the pope to wear mens clothes. She started using the male name of Antonio de Erauso, and went back to the America, where she established a business as a muleteer between Mexico City and Veracruz.

What movie does the guy dress up as an old woman?
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What movie does the guy dress up as an old woman?

After a bitter divorce, an actor disguises himself as a female housekeeper to spend time with his children held in custody by his former wife.After a bitter divorce, an actor disguises himself as a female housekeeper to spend time with his children held in custody by his former wife.After a bitter divorce, an actor disguises himself as a female housekeeper to spend time with his children held in custody by his former wife.

Mrs. Doubtfire is an extremely funny and heartfelt film. It has tons of laughs as well as tears, this is definitly Robin Williams best film. Watching williams do voices as well as play Mrs. Doubtfire is a real treat. Also the supporting cast of actors do an excellent job, I highly reccomend it.

What is the streaming release date of Mrs. Doubtfire in Italy?

Who is the friend in 27 Dresses?
(Image Source: Pixabay.com)

Who is the friend in 27 Dresses?

Judy Greer played Janes friend, Casey. Greers character offers advice to Jane throughout the film, frequently telling her she should be upfront about her feelings for George. Before appearing in 27 Dresses, she was in several films and was well-known for her role as Lucy Wyman in 13 Going on 30.

  • Katherine Heigl, James Marsden, and Malin Åkerman starred in 27 Dresses, which was released in 2008.
  • Heigl and Marsden have since starred on hit TV shows.
  • Åkerman and Judy Greer had supporting roles in 27 Dresses but are now Hollywood regulars.
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Its been 12 years since the popular romantic comedy 27 Dresses made its grand debut.


📹 OVER 70 BLACK MALE ENTERTAINERS THAT SAID “YES” TO THE DRESS AND MADE IT TO THE TOP IN HOLLYWOOD!

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White Male Actors Who Wore Dresses In Movies
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Christina Kohler

As an enthusiastic wedding planner, my goal is to furnish couples with indelible recollections of their momentous occasion. After more than ten years of experience in the field, I ensure that each wedding I coordinate is unique and characterized by my meticulous attention to detail, creativity, and a personal touch. I delight in materializing aspirations, guaranteeing that every occasion is as singular and enchanted as the love narrative it commemorates. Together, we can transform your wedding day into an unforgettable occasion that you will always remember fondly.

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  • It’s no more different than a fraternity club. They were willing to put on those wigs and makeup to be part of the club and make millions dollars and a lifestyle that is probably very nice. The way I see its no different than if somebody walked up to anybody here perusal this and said hey would you wear a dress if I gave you a million dollars how many guys would probably do that for the money….

  • Another point that needs to be talked about further is that on top of being forced to wear dresses, they are also dressed up in a very caricature-ish manner that portrays black women in the negative stereotypes we’ve become familiar with. Everything, from the make-up, to the dresses themselves, to the facial expressions and voice intonations is so over the top and negative. So on top of emasculating these men, they are also being made to continue hurting the image of their fellow black women.

  • The dress code didn’t just target one specific race. Here’s more prominent actors to add to this list: Robin Williams, Arnold Schwarzenegger, Tom Hanks, John Travolta, Dustin Hoffman, Peter Scolari, Philip Seymour Hoffman, Channing Tatum, Robert De Niro, Johnny Depp, Adam Sandler, Kurt Russell, Harrison Ford, Woody Harrelson and John Lithgow, to name a few.

  • It’s 100% a humiliation ritual. I say this as a white man. There has never been a single doubt in my mind that Hollywood elites despise all forms of masculinity, and since they already obfuscate their hatred for black people behind veils of tokenism, it’s obvious that black men suffer this fate the most. They even use excuses like “it’s just comedy” “it’s not that serious” to try and coerce black men to give in “Here’s your chance to make it big.” Take one look at all the celebs who refuse to wear the dress. Universally, their careers in Hollywood suffered. That’s what we call proof.

  • I get labeled homophobic for not willing to sacrifice my integrity and masculinity which pisses me off, my brothers on the other hand are unbothered by wearing a dress saying they would be comfortable doing so and even call themselves justifying it by saying men in Africa wear dresses, I have standards and principles that I refuse to break that doesn’t make me homophobic that means I have boundaries.

  • Even though a man putting on a dress or vice versa in the industry of entertainment I have to agree with Godfrey that white America feels threatened when it comes to black masculinity. As for Hollywood the industry was/is perverted and is an abomination on to the LORD THY GOD and the people who wickedly run that machine are Gay from the beginning. Just my OPINION it is what it is your own right and Choice.

  • Hollywood puts white actors in a dress too. Robin Williams, Arnold Schwarzenegge, John Krasinski, Tom Holland, Channing Tatum, John Goodman, Jared Leto, Eddey Redmayne, Patrick Swayze, Robert Downey Jr, Tom Hanks, Dustin Hoffman, Tony Curtis, Jack Lemmon, Evan McGregor, Christian Bale, Johnny Depp, Woody Harrelson, George Clooney, David Duchovny, Ian McClellan, Daniel Craig, John Travolta, Liev Schroeder, Cillian Murphy, Jude Law, Rupert Everett, James Franco, Kurt Russell, Benedict Cumberbatch, Chris Hemsworth, David Spade, Will Farrell, Dan Ackroyd, Fred Armisen, Chris Farley, Seth Myers, Phil Hartman, Dwayne The Rock Johnson, Michael Fassbender, James Franco, Benedict Cumberbatch, Johnny Depp, Ryan Gosling, Ryan Reynolds, Jake Gyllenhall, James McAvoy, Nathan Lane, Tim Curry, Jamie Farr, Woody Allen, Adam Sandler, Patrick Stewart, Robert De Niro, Steve Martin, Willem Defoe, Michael Keaton, Tom Hiddleston, Ewan McGregor, Steve Buschemi, Jeff Bridges, Bryan Cranston, Gary Busey, John Malkovich, Chris Evans, Neil Patrick Harris, Hugh Laurie, Stephen Fry, Rupert Everett, Jim Carey, William Macy, Michael J. Fox, Andrew Garfield, John Lithgow, Matt Bomer : 75 and there are more.

  • Great article but if you wanna be successful, you most take responsibility for your emotions, not place the blame on others. In addition to make you feel more guilty about your faults, pointing the finger at others will only serve to increase your sense of personal accountability. There’s always a risk in every investment, yet people still invest and succeed. You must look outward if you wanna be successful in life, Successful people don’t become that way overnight. most people see at a glance-wealth, a great career, purpose-is the result of hard work and hustle over time. I pray that anyone who reads this will be successful in life too 🙏🙏🙏

  • This was WELL DONE! A larger question to ask is why the campaign has been launched against Black Entertainers. If this strategy is indeed spiritual, one must conclude that our adversary has a lot to do with it. Could it be that our adversary and those who run Hollywood know who we are? But because we don’t know who we are and WHOSE we are….we fall for anything. Hmmmmm……

  • 2021…50plus yr old African American Man sitting here with tears in my eyes checking this article/audio out. WOW, who wants to be a movie star, rapper, singer, who eats caviar with the elite? Let Me Be Spiritual… You can’t be a YouTube sensation or rapper without someone/thing/how trying to hurt you…WOW

  • Chapell wore his dress early on in his career… “Robinhood Men In Tights…” Can’t believe how much this is glossed over in articles like this… Also, most of the big time stars put on a dress sometime regardless of race… It was heart breaking to see Ozzy do it… “We sold our soul for rock and roll…”

  • Black men have been under attack here in America from their first setting foot on the soil. As a young kid it was funny perusal skits by Flip Wilson pretending to be a woman. It’s unfortunate that these men literally sold their souls for fame and fortune. The Bible says a good name is to be chosen rather than great riches. Proverbs 22:1. These once amazing role models fell from grace right before our eyes and a host of youth followed. SMH. The handwriting was on the wall for all who could see it but earthly comforts were more important. This was a wonderful article.

  • It ain’t just “black” men at all. All men that want to go up wear the dress. Jim Carey, Milton Berle, and as far back as I can remember The Duke, John Wayne wore one as well. This isn’t a racial thing, it’s a domineering thing to demoralize any man that wants to move up. Even one of my favorite B-ball players as strong a manly as Dennis Rodman was, he succumb to wearing a “wedding dress!

  • And if you watch until the very end, you will see that Dave Chappelle wore the dress too. Looks like he did it in Men in Tights, which I think was one of his first movies besides Half Baked. They got him too. Kat William is the only true OG in this game who stands on his square. Much Respect to KW always!

  • Wow! I’ve read Iceberg Slim’s ‘Pimp’ and grew up perusal the Dave Chapelle Show, Half-baked etc but more importantly have followed Dave Chappelle’s story of what happened circa 2004 with the $50M contract, the dress, and Dave’s departure/retreat from Hollywood and subsequent refusal to re-sign with Comedy Central (he refused the $50M) when sought refuge in Africa. His 2006 interview on Oprah where he declared that “…Maybe the environment in Hollywood is a little bit sick!?!?…” followed by years of not being heard of until this “new” Dave re-emerged in 2018. Personally I haven’t heard the”new” Dave say anything even remotely resembles that of Dave Chapelle I know and love BUT the analogy that this new Dave uses in this clip pertaining to how a pimp and how Hollywood use the same manipulative tactics on their “talent” to keep them in the game even if it’s against their will/desire to continue doing so.

  • It’s a tough one guys, really tough. Because I really enjoyed White Chicks and Big Momma…they killed me with laughter. For the sake of the actors, when you have families and bills, these decisions are not as clear-cut as they seem for us outsiders. We really don’t know how these happened, some of them were probably tricked with contracts to wear dresses. All I know is, there are very few straight guys who are comfortable in a dress for any reason. Especially if they are super masculine like Michael Jai White.

  • Of course we prefer REAL sistas play the female parts. But when you’re an actor, aren’t you supposed to play whatever character is necessary to tell the story?🤷🏽‍♀️ I loved Eddie in “The Nutty Professor”. Showed his amazing talent. Women been prancing around in dresses, and painful high heels forever. Who cares if a handful of men have a little taste of it?!😆 I was more traumatized with Ving Rhames in that “Pulp Fiction” scene🥺

  • Kevin should not be respected, Ever. He said all that crap about the brand and never wearing a dress then when it was time they placed him in a dress like a good little puppy. Smh Also, people keep saying follow Dave Chappelle, but they should be learning from and following Katt Williams because they actually got Dave at the beginning of his career then it took off. JSaà

  • I just watched an old episode of New York Undercover. The stars of the show they had them in dresses.The guy that played on tv show Scandal Ovilia Pope dad was in a dress to. Then I seen this on YouTube and was like it’s definitely a thing for them to put black men& Latino men in dresses in Hollywood.

  • This is psychological. Those from outside see our masculinity as our strength. So when one of us gains prominence, the first attack is at that…But never directly. It always comes as an afterthought but if you say no, that’s the end of your trip. The psychological part is them saying, “sure, we know you’re a man, but you wanna make it don’t ya?” So in that question, they want to see what’s most important to you: your manhood or your accolades. With that question, they also checking to see how deep your beliefs go. If you show, even in a moment of weakness that you could go where they tell you, you’ve essentially shown your breaking point…the point where money/fame outshines your will and manhood. Even if it’s a one time payment, you will continually have that as a blemish on whatever you do after that.

  • 1) (well-known names presently – White actors/comedians in drag) Charlie Chaplin (“The Masquerader”, “A Woman”), Lon Chaney (“The Unholy Three”; 1925); Marlene Dietrich (“Morocco”; 1930); Greta Garbo (“Queen Christina”; 1933); Stan Laurel (“Babes in Toyland”; 1934); Katherine Hepburn (“Sylvia Scarlett”, 1935); Lionel Barrymore (“The Devil Doll”; 1936); Harold Lloyd (“Professor Beware”; 1938); Carey Grant “Bringing Up Baby”; 1938; Lupe Vélez (“Honolulu Lu”; 1941); “This Is the Army” – Ronald Reagan stars as Lt Johnny Jones, the producer of an all US Army musical revue, featuring a performance of soldiers in drag; Elizabeth Taylor (“National Velvet”; 1944); Alec Guinness (“Kind Hearts and Coronets”; 1949); Gloria Swanson (“Sunset Boulevard”; 1950); Janet Leigh (“Houdini”; 1953); Bob Hope (“Casanova’s Big Night”; 1954), Bing Crosby and Danny Kaye (“White Christmas”; 1954); Lou Costello from Abbott & Costello (“Abbott and Costello Meet the Keystone Kops”; 1955); James Cagney (“Man of a Thousand Faces”; 1957); Anthony Perkins (“Psycho”; 1960);

  • Praise Hayah, all you nations! Extol Him, all you peoples! For His loving-commitment is mighty over us, and the truth of Hayah is everlasting. Praise Yah (Psalm 117) ! // SHLM & HaB (peace & love). The Name of the Creator is Hayah asher Hayah, as what He told Moshah (Exodus 3:14), preserved in the Hebrew Scriptures. There is a curse to the G-o-d name (Isaiah 65:11-12), preserved in the Hebrew Scriptures. All followers of the Messiah are to do the 7 appointed times (Leviticus 23), but no more animal sacrifices, following the Crucifixion of the Messiah. We are now of the order of MLK TSDQ (King, righteous), to Whom ABRaHM tithed. Ask the Messiah to be your personal Savior. He said to him, I am the way, the truth and the life. No one comes to the Father except through me (John 14:6). All have sinned and fallen short of the glory of Hayah (Romans 3:23). The wages for sin is death but the gift of ALaHYM is Everlasting Life through Messiah Yahushgh our Master (Romans 6:23). That if you confess with your mouth the Master Yahushgh and believe in your heart that ALaHYM raised Him from the dead, you shall be saved (Romans 10:9). He Himself is an Atoning Offering for our sins, and not for ours only but also for all the world (1 John 2:2). The Messiah died on the cross, & Resurrected three days later (presenting Himself as First Fruits to the Father). Please ask Him to be your Savior. He is the ONLY way to Everlasting Life.

  • The two successful actors that I haven’t seen in a dress are Morgan Freeman and Denzel Washington. However, I haven’t seen every bit of entertainment media they’ve done. Maybe they had 10 second spot in a commericial when they were just starting out or something, and if that appearance in drag never happened in their caeers, then what else have they done to avoid the dress shaming?

  • The only person on this list with an asterisk on his name should be Dave Chapelle. He was on the other side, saw how it treated people who went to those lengths, and spilled everything. He was the 1 brave warrior who put himself on the line to come back and let the world know how it really is. I have nothing but respect for that man.

  • So why is this rule not the same when women dress up as men? I’m not saying that there isn’t some craziness going on in Hollywood but some things are just so far of a reach from people who have never been in the entertainment business. It’s like people telling you what to do in the record industry that have never made a record.

  • I forgot about the scene in Robin Hood Men In Tights but I have to say that one I understand why he did it. As you see in that scene, all of the men are dressed as women, to sneak into somewhere without getting caught. But they don’t look even a little like women and none of the characters had to act any less masculine, because the humor of the scene was how much they were not pulling it off. I think that scene was a matter of context and Dave must not have felt the same way about it. I wish they had him addressing that scene in an interview. I’m real curious about his response.