Two African-American men trying to pass themselves off as very, very, very white women? Sounds preposterous. But with the help of an FBI friend, who just happens to be a genius with make-up, that's exactly what the hapless Marcus and Kevin Copeland (Marlon and Shawn Wayans) do when they go undercover as Hamptons' socialites Tiffany and Brittany Wilson.
The idea for White Chicks came from Shawn Wayans, says his brother, director Keenen Ivory Wayans. "We were sitting around reading magazines and one of them had a story about Hamptons socialites. Shawn was reading the interview and laughing. 'Me and Marlon should play girls like these,' he said. I thought it was a brilliant idea. Now it's not a movie about anyone specifically but about that world of seeing and being seen. I knew if we did it, it would be hysterical. But I wanted to be sure that they looked convincing. That was the real challenge."
While White Chicks plays with the world it inhabits, as with all comedies by the Wayans, it's also a running commentary on dysfunctional behavior. In this case the "high society" of the Hamptons becomes the perfect canvas for a comedy that also explores the themes of perfection vs. insecurity, love vs. belonging.  It is this skillful blend of comedy and social commentary that makes a Wayans film stand out from other comedies. 
Rick Alvarez, long-time producing partner to the Wayans Brothers, mentions that the they spend a great deal of time researching their subjects, "dissecting things, coming up with the most obscure bits of comedy that, when put together, create these insane, unpredictable scenes. They have a history of poking fun at pop culture and the world, but they dress it up in a really funny way so you almost forget you're also exploring important themes."
"Keenen Ivory Wayans is one of the greatest comedy directors of all time in my mind," enthuses producer Rick Alvarez.  "Then you have Shawn and Marlon who are incredible performers, who have been doing great character work since 'In Living Color.' You put these three together and it's kind of a no-brainer. It was an easy concept to sell."
Producer Lee R. Mayes, who started his relationship with Keenen on Lowdown Dirty Shame, adds that the brothers had more than just their reputation to sell, they also had an original idea. "I don't think anybody has taken two young black men and tried to make them two young, attractive blonds," says Mayes.
"There was Some Like It Hot, but they looked like two dowdy ladies.  Same with Mrs. Doubtfire.  True Identity was an early film that did a good job of turning a black man into a white man. Eddie Murphy did it on 'Saturday Night Live,' which was an inspiration for the film.  But we wanted to amp it up to another level. We knew it would be an extraordinary achievement if we could pull it off."

MAKING THE ILLUSION REAL
The film's creators were determined to make the illusion as real as possible rather than rely on the more conventional "drag" look.
A crucial element was casting.
The filmmakers searched for two young women who not only looked like sisters but who were close enough in height and weight to Shawn and Marlon and whose faces could "fit" the Wayans'.
Maitland Ward, who was chosen to play Brittany Wilson, vividly remembers the offbeat casting session. "After I read for the role I had to have my face measured," she recalls, "the distance between my eyes and my nose and my lips and chin. Then they had to make a plastic mold to make sure it would fit with Shawn's features.  It was one of the most unusual auditions I've ever been on."
Realizing the difficulty of the transformation, the creators hooked up with special effects make-up artists Greg Cannom (who won an Oscar^® for Mrs. Doubtfire) and Keith VanderLaan.
Together they came up with a new design, creating and testing several different types of prosthetic devices before settling on those used in the film. The actresses' faces were divided into four sections so that individual parts could be modified as needed without having to start over from scratch each time. Once the shapes were determined, there were extensive make-up tests.
His first challenge, says Cannom, was to soften Shawn and Marlon Wayans' chiseled features without creating flat, lifeless faces. Once that problem had been surmounted, Cannom was confronted with another dilemma -- all the beauty enhancing make-up tricks women normally use had the opposite effect when applied to men.
"The interesting thing," says Cannom, "was that in order to make them look attractive, you couldn't use any make-up. Otherwise they started looking like drag queens. So even though I used corrective make-up to soften them, for the rest of the face a more subtle approach was needed."
Tougher still was finding a body paint to cover up the men's dark skin that didn't look unnatural or painted on.
"What usually happens when you apply a light color to skin like that," explains Cannom, "is that it turns gray. To compensate for that, we had to create something new, a mixture that we sprayed on the skin to help fight the gray.  We found a make-up called Revlon Color Stay. After applying a first coat of my product to seal the skin, we put Color Stay over that and were able to get a really light tone. On top of that we spattered some fine freckles and tiny reddish spots to break it up a bit and achieve a realistic-looking skin tone."
"I remember the first time we did the tests I was standing a foot away from Marlon," Cannom continues, "and he had the contact lenses in for the first time, as well as the make-up and the wig. It really freaked me out because there was nothing of Marlon there. For a second it unnerved me.  I've never had that reaction before.  So I knew it had to be pretty good."
Then the Wayans brothers arrived in full make-up at Revolution Studios, the film's financial backers.
"That was a golden moment," recalls Mayes. "Shawn and Marlon were just hilarious. They jumped into their characters so quickly that we forgot what the test was for. They had instantly transformed themselves into two young women. It was mind-bending."
Alvarez agrees that the tests succeeded beyond everyone's expectations.  "It was outrageous," he laughs. "They were dancing like white girls, talking like white girls. They literally became white girls in front of our eyes.  It was brilliant."
That blind devotion to the muse of comedy also held true for the director's co-conspirators, Shawn and Marlon Wayans. They endured five to six hours of prosthetic and make-up application every day. They each lost 30 pounds to appear more svelte and lithe. "I think all the actresses were unnerved by us in a way," laughs Shawn. "They actually forgot that we were black men under there. We were privy to a few of those conversations that grossed us out. Too much information." 
VanderLaan commends Shawn and Marlon for their patience in the make-up chair.    "We'd be working away for hours, concentrating, and they couldn't move," he says. "They just had to sit here and go through it and then spend the whole day acting.  When they wrapped, we had to take it all off very slowly so we wouldn't ruin their skin. It was a grueling process. We expected them to lose it at some point but they never did. Their patience was amazing."