This Friday, Martin Lawrence's Big Momma's House franchise embarks on its third outing (Big Mommas: Like Father, Like Son) in an attempt to pass the gender-bending comedy torch to a new generation. The "men in dresses" subgenre, however, is nothing new. Why, fellas have been going undercover as ladies for years on the silver screen! (And, believe it or not, Tyler Perry is not the reigning box office king of cross-dressing comedy.) Hit the jump as we count-down the most bankable cross-dressing male movie stars of all time.
First, a few ground rules. We'll focus on films in which men don ladies' garb as disguise and not, say, dramas such as The Crying Game, female cross-dressing films like Just One of the Guys, or films like The Rocky Horror Picture Show or The Adventures of Priscilla, Queen of the Desert, which feature transgender/transsexual characters. (Tyler Perry's Madea character, though genetically female, is included on the basis of the transparency of Perry's performance.)
And so, without further ado, behold America's most beloved cross-dressing male stars, ranked in order of box office love:
10. Eric Idle & Robbie Coltrane, Nuns on the Run $10.9M
The "hiding out from the mob in the church" gag had been done elsewhere, and better (namely, a year earlier in We're No Angels) before this 1990 British nun-sploitation comedy starring Eric Idle and Robbie Coltrane notched a modest $10.9M North American box office showing.
9. Miguel A. Nunez, Juwanna Mann ($13M)
A cocky male basketball player finds salvation -- and love, natch -- by masquerading as a WNBA hoopster in this terribly-received 2002 comedy. Portrayed by character actor Miguel A. Nunez (who made his bball comedy debut in Slam Dunk Ernest, though not in drag), Juwanna Mann taught audiences the ultimate lesson in basketball etiquette: go for the backboard-shattering slam dunk, and your showboating can cost you. (That is, if your wig flies off and the world realizes you're really a man.)
8. Jonathan Brandis, Ladybugs ($14M)
Similar stakes were at hand in this beloved 1992 kids sports flick, in which Rodney Dangerfield enlists his girlfriend's son (Jonathan Brandis, swoon) to dress like a girl to lead his soccer team to the championships. Paired with the Chuck Norris fantasy pic Sidekicks, Ladybugs made a teen idol out of young Brandis -- but it only stayed in theaters for three weeks.
7. Jack Lemmon & Tony Curtis, Some Like it Hot ($25M)
Billy Wilder's 1959 hit about two musicians who hide out from the mob in drag (clearly, mobsters are the dumbest villains in movie history) not only tipped the box office at $25M, it also won an Oscar and earned five additional nominations including Best Director, Best Screenplay, and Best Actor.
6. Shawn and Marlon Wayans, White Chicks ($70M)
Sometimes men in dresses work better in pairs than alone (see: Some Like It Hot). Other times, twice the cross-dressing means twice the freak-out factor, as in the Wayans bros. comedy White Chicks. Granted, the terror owed more to the whiteface than what Shawn and Marlon were wearing as two African-American FBI agents/brothers who go undercover as, well, blond Caucasian women. Despite the frightening prosthetic work and White Chicks' five Razzie awards, it debuted at #2 with a $19M opening weekend and went on to make over $113 worldwide. A sequel is reportedly in the works, so consider yourself warned.
5. Tyler Perry, Tyler Perry's Madea Goes to Jail ($90M)
The grand dame of modern male cross-dressing in the movies is, hands down, Madea -- or rather, her portrayer and creator, multi-hyphenate Tyler Perry. Taken as a whole, Perry's theatrically-released cinematic filmography has raked in over $519M worldwide in ten feature films, though the character of the feisty matriarch Madea, played by Perry in disguise, has only shown up in five of those films. And of those five Madea films, Madea Goes to Jail -- the popular character's most prominent starring vehicle -- earned the biggest box office at $90M. Can her next outing, April's Madea's Big Happy Family, top her biggest performance to date?
4. Martin Lawrence, Big Momma's House ($117M)
Tyler Perry might have conjured a cultural movement with his Madea character, but he has Martin Lawrence to thank for leading the cross-dressing charge in contemporary comedy. (Lawrence, in turn, can thank Eddie Murphy for leading the fat-suited revolution with his 1996 vehicle The Nutty Professor.) 2000's Big Momma's House introduced audiences to Lawrence's undercover FBI agent Malcolm Turner, who pulls a Mrs. Doubtfire to catch a criminal. Big Momma's House notched a surprising $117M domestic box office, kicking off a franchise that continued with the less successful sequel Big Momma's House 2 ($70M domestic/$138M worldwide). Does the series have enough juice to propel a second sequel, this week's Big Mommas: Like Father, Like Son, to the top of the box office? A better question: Doesn't franchise newcomer Brandon T. Jackson deserve a better fate than this?
3. John Travolta, Hairspray ($118M)
John Travolta's gender-bending turn in the 2007 remake Hairspray may not have been the main attraction, but it was a scene-stealing performance nonetheless. The family-friendly update of John Waters' 1988 comedy featured Travolta in the role made legendary by Divine, and though Travolta didn't quite fill Divine's pumps, his be-wigged, fat-suited turn was an oddity and an attraction that helped boost the musical to a $118M domestic box office.
2. Dustin Hoffman, Tootsie ($177M)
In Tootsie, aging actor Michael Dorsey (Dustin Hoffman) moonlights as an actress and becomes a popular soap opera star -- a premise copied liberally in subsequent cross-dressing comedies, but overwhelmingly appreciated by American audiences upon its release in 1982. The difference between Tootsie and, say, Juwanna Mann? Tootsie notched ten Oscar nods, including a Best Supporting Actress win for Jessica Lange. The acclaim helped the Sydney Pollack-directed pic reign over the box office for a whopping 13 weeks; it eventually racked up a $177M domestic box office return.
1. Robin Williams, Mrs. Doubtfire ($219M)
If you're Tyler Perry, here's who you should be studying: Robin Williams, whose turn as the lovable, plump housekeeper Mrs. Doubtfire (really an estranged father who disguises himself in drag to spend time with his children) won over America's hearts and pocketbooks during the 1993 holiday season. After debuting over Thanksgiving weekend, the Chris Columbus pic held a spot in the Top 10 for 19 weeks on its way to a whopping $219M domestic performance -- and, just as impressively, Mrs. Doubtfire earned even more ($222M) overseas, making Robin Williams not only America's favorite cross-dressing male star of all time, but also the entire world's.
Box office reports courtesy of Box Office Mojo
