How To Roast Someone Like A Pro 

You probably know that Michelle Wolf delivered the standard "roast" at the White House Correspondents' Dinner over the weekend and delivered some choice lines skewering the Trump administration and the media. From the reaction, you'd be forgiven for thinking that Wolf spent the entire evening mocking Sarah Huckabee Sanders' looks.

Photo: Tasos Katopodis/Getty Images for Netflix

Even Maggie Haberman, the White House correspondent for the New York Times, weighed in with a truly baffling misapprehension of Wolf's remarks:

The remarks on the press secretary's makeup were, in fact, a set-up for a joke about Sanders' penchant for lying. Here's the entirety of Wolf's jokes about Sanders:

We are graced with Sarah's presence tonight. I have to say I'm a little star-struck. I love you as Aunt Lydia in The Handmaid's Tale. Mike Pence, if you haven't seen it, you would love it.

Every time Sarah steps up to the podium I get excited, because I'm not really sure what we're going to get - you know, a press briefing, a bunch of lies, or divided into softball teams. "It's shirts and skins, and this time don't be such a little bitch, Jim Acosta!"

I actually really like Sarah. I think she's very resourceful. She burns facts, and then she uses that ash to create a perfect smoky eye. Like maybe she's born with it, maybe it's lies. It's probably lies.

And I'm never really sure what to call Sarah Huckabee Sanders, you know? Is it Sarah Sanders, is it Sarah Huckabee Sanders, is it Cousin Huckabee, is it Auntie Huckabee Sanders? Like, what's Uncle Tom but for white women who disappoint other white women? Oh, I know. Aunt Coulter.

There is literally nothing here mocking the Sanders' appearance. Every joke is about her daily assault on truth and her role as the female enforcer of a patriarchal regime (the Aunt Lydia joke, if you aren't familiar with The Handmaid's Tale).

But let's imagine, for a moment, that Michelle Wolf did go too far. To get an idea of how a comic can know what's working and what isn't, if they have crossed a line, and if they need to apologise, I spoke to Jean Villepique, a Second City alumna and a series regular on NBC's AP Bio.

First off, what is supposed to happen at a roast?

In an ideal world, a roast is poking fun at someone's foibles - it should have, as Villepique says, "a playful and tough tone."

And the hallmark of a roast, says Villepique, is that you are willing to get as good as you give. The roasts on Comedy Central, she points out, showcase the comics making fun of each other. The Trump administration, which has made its fair share of jokes - about ugly women, for example - isn't taking this in stride.

But is Michelle Wolf taking the criticism in stride, or is she getting all worked up and pissy about it, as defenders of Sanders are? I'd say Wolf is managing pretty well:

The Trumpers seem pretty butt-hurt for a joke about eye shadow. "The conservatives lack a sense of humour in many ways, and are threatened by the truth that comes out in comedy," says Villepique. "Their trolling on Twitter is the perfect example - I will roast you but I won't [allow myself] to be viewed by the same lens."

So how do you know if your jokes are working?

When Villepique worked on political comedy at Second City, "we knew something landed when someone laughed. When we shined a light on something in the right way, the laughs told us."

Now obviously this is a little harder at the WHCD, when the comic is making fun of the whole room, including the media. But plenty of people in TV land were laughing at Wolf's routine, including her peers in the comedy world - so she knows she did something right. If her jokes had focused on a woman's looks - as Trump's often have - no one would be laughing.

"When we went too dark, we wouldn't get laughs - we'd get groans or boos."

How do you know your joke has gone too far?

When's there's silence, says Villepique. "I'd rather have boos or groans than silence. Silence is a disconnect."

So, even if some people are outraged, how can you know if you've done your job?

The role of the comic is speaking truth to power. "If you are shining a light on the truth of someone's behaviour in a way that is satirical, then that is the job," says Villepique.

You know you've done the job when you've said something that's both true and profound - and people are laughing. "The comic's role is to ring a bell and tell the truth," says Villepique.

Wolf has drawn especial outrage because she - unlike a lot of the media - isn't pretending any of the current US political situation is normal. "I think the truth is so awful right now that her speaking it shook people. When the behaviour has gone so far in one direction in our country, when the truth is at stake, it's hard to just say, 'we're going to keep it light,'" says Villepique.

Wolf ended her speech not with a joke but with a bald statement of truth, the only unfunny thing she said all evening. So if you want something to be outraged about, chew on this: Flint still doesn't have clean water.


Comments

    I watched the whole segment, some jokes hit, some jokes missed. There were also jokes about Chris Christie's weight, so this faux outrage about appearance based jokes is just hilarious.

    But in between the standard one liners about Sarah Sanders being a liar, or Trump not having any money there were really hard hitting jokes and comments that held up a mirror to the joke that is the murica.

    Jokes about the fact that the media practices access journalism or flint still not having clean water. I think ultimately that's what the media is really outraged about but can't say publicly.

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