I am a fan of envelope pushing.
I have always enjoyed laughing at someone toeing the line between "funny" and "in poor taste." The only way I can put it is that it doesn’t always offend me to be offended.
Comedy is weird that way, in that it can be just as satisfying to groan as to laugh. You can be kind of mean, use bad words and occasional slurs, cross social taboos, and make the audience cringe, as long as you’re ultimately funny; plain and simple.
It's hard to say what makes for that delicate balance, though. It's a mixture of projecting self-awareness, intelligence and ultimately, kindness. There's also creativity -- nobody wants to hear the same hacky jokes about black people and white people or men and women, but a really creative, well-crafted joke can be about... well, almost anything.
Thus, the difference between "Work It," the thoroughly abhorrent, unbelievably derivative drag comedy, and the work of other comedians like Chris Lilley, who has dressed as male, female, black, white, Asian, twins, and more, with what can only be described as "finesse."
Some of the best comedians address gender in a way that ameliorates potential chafing with sheer brilliance -- include Louis CK, Margaret Cho, Chris Rock, Ricky Gervais, Tina Fey and Wanda Sykes. Even, some might say, "Raw"/"Delirious"- era Eddie Murphy.
I fully believe that these principles can be applied to drag. I laughed at "Shit Girls Say" -- and not because I hate women or because I think the guys behind the video did. Jezebel wrote of the web series, "Honestly? Funny because it's true, except for the part where guys dress up as women in order to mock them."
Honestly? I generally think a funny male actor dressing as a woman is hilarious.
Whether it’s total camp (Milton Berle’s shtick in the '50s, or Jack Lemmon and Tony Curtis in “Some Like it Hot”) or something more earnest and thought-provoking (performers like Divine and Lady Bunny), I honestly think we respond to the comedy of it on a deeply human level.
Eddie Izzard addresses the strange business of identifying as a transvestite and turns it into comedy, but while you're laughing at his stories, you're never really laughing at the fact that he's a guy wearing high heels and lipstick.
When Terry Gilliam puts on a dress and plays Dennis's mother in "Holy Grail," you can laugh the fact that, quite honestly, he makes a ridiculous "old woman." Done well, it's a brilliant kind of physical comedy. I guarantee you ancient cavemen were pretending to be their wives for the delight of their clan, and that it killed.
I’ve been a huge fan of the "Shit [Insert Demo Here]s Say" series, because I think the jokes ("That dog needs WATER") are spot on and hysterical. The argument that I've heard is that it trades on the idea that a guy dressing up like a woman is somehow funny in itself, which is offensive to women and transgendered people. But come on -- there's a difference between a transgender person and a dude in a dress in a web video.
Funny is funny, and stuff that's meant to be malicious or hurtful isn't funny. I think it works best because it’s a pointed character study. Like when you think to yourself, "I know this girl. Hell, I’ve been this girl."
It's not just about not being overtly mean spirited. It means keeping it very tongue in cheek and well executed.
Now, "Work It" is plainly offensive, cheap, stupid and low brow. Take the premise: Two down-on-their-luck schmos dress in drag to get a job in this awful economy and, “…must put aside their alpha male selves and learn to navigate their all-female workplace.”
OK, this is the biggest crock of shit ever. Obviously, “Bosom Buddies” was a different time, rife with antiquated notions of gender and leftover from the "sexual revolution." To try to spin it into a modern show and revolve it around a notion that two dudes can’t get work as sales reps because they aren’t hot chicks is not insulting, it's dumb as shit. I never heard the term “mancession” before and I never want to again. There's no "shock of recognition" here, because the concept is patently false.
On the other hand, take Chris Lilley, the Australian creator, writer, director and star of HBO’s "Angry Boys" and the classic "Summer Heights High."
The shows are similar to “The Office” in that they’re in segmented, faux documentary format. Every show has a couple main characters played by Lilley -- among them are “Summer Heights High”'s horrid, bitchy private school girl Ja’ime and a Tongan teenager. Lilley is a 37-year-old white man. The show worked flawlessly.
He plays women in "Angry Boys," too, from a correctional facility employee to a Japanese stage mom. He plays twin brothers, where one is deaf and constantly teased by his full hearing brother. He even taunts us with what can technically be called blackface, as rapper “S. Mouse” who pretends to be from the hood, but grew up rich in Calabasas. S. Mouse sings songs about taking dumps on the hoods of police cars and slapping your elbow. They’re catchy tunes, too.
The difference between this working and this So Not Working is a kind of strange alchemy. I'm loathe to use this comparison, but it's like the old chestnut about the difference between art and smut: you know it when you see it.
I think when it's done well, you don't really think about the fact that, huh huh huh, it's a white man dressed as a woman or black lady dressed as a Laotian cop. The whole point is finding the humanity in the completely ridiculous, and the completely ridiculous in humanity. And that's pretty funny.