Ironic Justin Trudeau Halloween

Dear Hipster:

I read where you gave the wise advice, “Anytime you want to try blackface - DON’T.” But what if you want to go as Justin Trudeau in blackface? Isn’t that meta enough?

— M.

I’m picking up what you’re putting down: artfully sending up the Canadian PM by highlighting how his multiple blackface party appearances in the Nineties belie his trenchantly progressive social policies, or at least make him look the 21st-century political hypocrite. Done right, this could be ironic hipster satire at its purest. I’d be talking about this for a solid decade if I saw it at a party this year. At the same time, it invites flirtation with hipster racist disaster.

All hipsters have at some point quietly entertained the private belief they could have been stand-up comics if they had not dedicated their talents to furthering the art of being the first person at the newest bar in the neighborhood. If you aren’t laughing at the world, you can bet the world’s laughing at you. And jokes can be their sharpest when they hit right on the edge of acceptable. Nobody knows exactly where lies the line between “edgy” and “improper.” Hipsters, like the comics they wish they were, skirmish across that line like 1980s siblings sneaking a fingertip across the DMZ at the center of a station wagon bench seat, except instead of drawing out a “Mom, he’s on my side,” you might get a “Oh hell NO you $&#@ing didn’t!”

Recently, Saturday Night Live hired, and then promptly fired, comedian Shane Gillis because Mr. Gillis, it turns out, is unabashedly bigoted in his comedy. Gillis wasn’t offensive in the funny, transgressive “pushing boundaries” sense we associate with comedy greats cast in the mold of the late Richard Pryor. Instead, Gillis looked more like a not-particularly-funny person taking cheap shots, then excusing himself with, “I’m a comedian, and it’s a joke, so clearly I can’t possibly mean it.” All the while, he gave off the distinct impression that he did in fact mean it.

This is the risk you run with ‘Naively Racist Justin Trudeau’ on Halloween 2019, at least if you fully commit to the minstrelsy. In your heart, can you be 100 percent sure you aren’t the teensiest little bit delighted at an excuse to transgress purely for transgression’s sake? Even if you mean it as the purest form of arch political satire, not reveling in the sheer wrongness, can you be 100 percent sure it’s nonetheless OK? You can’t, because of that mysterious line between funny and wrong. Your costume concept is for sure marooned out there in No Man’s Land, waiting to step on a social landmine, or fall victim to the well-aimed artillery of basically anyone who isn’t you.

Me, I might duplicate one of Trudeau’s ill-conceived blackface costumes — perhaps the one from the rafting adventure — right down to the most minute detail, except I wouldn’t go so far as to actually black up. Carry a tin of Kiwi shoe polish, thus completing the “Justin Trudeau Mere Moments From Making a Terrible, Terrible Mistake” look.

Dear Hipster:

I read your Halloween column with interest this year. In my opinion, the Bedsheet Ghost is the best corny costume ever. Would it be ironically funny if I went out for Halloween as a Pointy Headed Bedsheet Ghost?

— Dan

No.