The following movies, whether standalone or part of a series, all feature men dressing in drag for roles that have become iconic over time. And they're all personal favorites of mine.
Madea
Tyler Perry's performance as Mabel "Madea" Simmons is one of the most convincing drag portrayals I've ever seen. I sometimes forget that Madea is being played by a man while watching.
Perry really fleshed out Madea's mannerisms and personality, and the costuming is perfect; the wig, makeup application, jewelry, and modest yet feminine outfit choices really tie the character together and help hide anything that might shatter the illusion.
Just look at the scene above from "Madea's Family Reunion" where she tries to avoid becoming a foster mother by ranting about how God gave women menopause for a reason. The comedic portrayal is flawless.
Mrs. Doubtfire
It comes as no surprise that Robin Williams used his keen impression acting skills to create such a convincing character when he portrayed the titular character in "Mrs. Doubtfire."
Between the costuming and mannerisms, you really wouldn't know that Mrs. Doubtfire was portrayed by Williams if you didn't see the transformation and other small hints that are intentionally slipped in for comedic effect.
If Williams was still with us, I'd pay to see a collaboration between him, Tyler Perry, the Wayans brothers, and Brendan O'Carroll.
White Chicks
Marlon and Shawn Wayans may not always be accurate in their portrayal of women in "White Chicks," with the duo going back and forth between exaggerations and the bare minimum, but the effort is clear, and the movie actually does address some of women's interests and insecurities.
Likewise, despite the uncanny valley effect of their masks—which was explained away as being the result of "plastic surgery"—the duo does pull off a convincing performance with regard to style and mannerisms.
And, I have to admit, they've got us pegged regarding the obsession with Vanessa Carlton's "A Thousand Miles." But to be fair, part of why I like the song so much is because of how it's used in the movie, especially in the scene with Terry Crews' character.
One thing is for certain though, all of these movies and their respective drag portrayals are iconic aspects of pop culture.
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