“A Run-By Fruiting” (#57)


The late, great Robin Williams played many iconic characters in the 90s, including Aladdin’s Genie sidekick and a grownup Peter Pan. But nothing showed off his talents for manic physical comedy and rapid-fire zingers quite like 1993’s family comedy Mrs. Doubtfire. It may just be his signature role — at least, for kids who grew up in the 90s.

In the latest When We Were Young podcast, we look back at the tradition of funnymen dressing as funny-looking women, from Tom Hanks in the awkward sitcom Bosom Buddies (1980) to Dustin Hoffman in the Oscar darling Tootsie (1982) to Martin Lawrence in the raunchy Big Momma’s House (2000). Then, it’s time to say “Hellooooooo!” again to Euphegenia Doubtfire, the silver screen’s most successful cross-dresser. Williams plays Daniel Hillard, an out-of-work actor who takes on the alias of a no-nonsense nanny to spend more time with his estranged family. (That’s what any loving father would do! Right??)

We also discuss the thin line between acceptable Movie Dad behavior and criminal offense, depictions of divorce in 90s movies, and ponder the broader question of whether gender-bending comedy still works in the more enlightened, less binary 21st century. So pad that bra and tuck accordingly — before Child Protective Services removes this podcast from your custody.


Listen to the podcast here or on iTunes.

Cross-dressing in entertainment has been around about as long as entertainment itself. It was the norm in ancient Greek theater, and later, more famously, in performances of Shakespeare. Male actors played female roles — because God forbid women should act — and, in plays like As You Like It and Twelfth Night, Shakespeare often had his males dress as women for comedic effect.

The tradition carried on in cinema, in early works like 1915’s Charlie Chaplin comedy A Woman, and 1947’s Boy! What A Girl!, but the gold standard is definitely 1959’s Some Like It Hot, directed by Billy Wilder, starring Jack Lemmon, Tony Randall, and Marilyn Monroe. Despite mixed reviews, it was nominated for 6 Oscars, including Best Director and Adapted Screenplay, and won one for Best Costume Design. It’s now considered one of the best screen comedies of all time.

The 1980 Tom Hanks sitcom Bosom Buddies is not. Perhaps that’s because the show’s creators didn’t really want to put the male leads in drag — but that was mandated by the network. It only lasted for two seasons.

But 1982’s Tootsie righted Bosom Buddies‘ wrongs, grossing $177.2 million in the U.S. and nabbing 9 Oscar nominations, winning for Jessica Lange’s phenomenal turn as Dorothy’s unwitting love interest. Dustin Hoffman is pretty incredible — and pretty believable — as a downtrodden actor who dons drag to play a no-nonsense hospital administrator on a soap opera.

Directed by Sydney Pollack, and co-starring Teri Garr, Bill Murray, and Geena Davis, Tootsie is remarkably fresh in 2019, with a surprising dearth of low blows that demean women or emasculate the protagonist. Hoffman’s Michael Dorsey is fully committed to his role, and not self-conscious about the lengths he goes to to nail a great part. Like Some Like It Hot, Tootsie is not just ahead of its time. In many way, it’s ahead of our time.

November 24, 1993

Budget: $25 million
Opening Weekend: $20.5 million
Domestic Gross: $219.2 million
Worldwide Total Gross: $441.3 million

Which brings us to Euphegenia Doubtfire, the tough love nanny invented by Robin Williams’ Daniel Hillard in Mrs. Doubtfire. By 1993, this trope was starting to show a few signs of gay panic, as Daniel has to explain to his disturbed son that he doesn’t “like” dressing like a woman. (The psychological damage done to these children deserves to be examined, but the gender-bending should be the least of their problems.) Overall, Mrs. Doubtfire remains the ideal showcase for Williams’ talents, with laughs and heart in equal measure.

Mrs. Doubtfire is the top-grossing cross-dressing comedy of all time, and the last one that remains in good standing. Afterward, we got Big Momma’s House (2000), Sorority Boys (2002), White Chicks (2004), and then a last gasp in ABC’s Work It (2012), canceled almost as soon as it aired. (Talk about about diminishing returns.) This kind of comedy is dormant, if not completely dead, on the screen — it’s hard to imagine how this premise could be tackled in a way that didn’t spawn outrage.

But the man dressed as a fat lady has not yet sung — Some Like It Hot, Tootsie, and Mrs. Doubtfire are all set for revivals as stage musicals in the near future. Let’s hope they don’t end up being more problematic than the decades-old source material, which holds up pretty well in 2019.


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