In November 2016, when Michelle Wolf was offered the opportunity to film her first stand-up special for HBO, the comedian set a challenging path for herself to make sure that her material was as solid as it could possibly be.

As Wolf explains, when it comes to comedy specials, HBO is the “gold standard,” so when the premium cabler called—while she was in Miami opening for Louis C.K., “pre-controversy”—she decided to embark on a 100-show tour prior to taping, where she would headline and mercilessly refine her material. “The one thing I’ve always heard from comics is, you always find tags and parts of jokes after you tape, and I didn’t want to do that,” Wolf explains. “I wanted to explore every premise and be as prepared as possible.”

A former contributor and writer for Late Night with Seth Meyers and The Daily Show with Trevor Noah—who this year led her own short-lived talk show, The Break with Michelle Wolf—Wolf worked tirelessly to make a strong first impression with her stand-up debut, Nice Lady, and succeeded in this endeavor, earning her first Emmy nomination for Outstanding Writing For A Variety Special.

HBO

Further illustrating Wolf’s fearlessness, chops, and command of the stage, the comedian this year turned the White House Correspondents’ Dinner into a global spotlight for her rip-roaring, no-holds-barred material, incurring the wrath of President Donald Trump and the news media with her well-calculated decimation of both. Hearing repeatedly about the challenge posed to any comedian in front of this typically hostile audience, Wolf’s only option was to disregard that room completely, performing instead for those watching at home. “Because if it’s not a good room, no matter who’s doing the show, then f*ck the room,” she says.

What was your goal as you set out to film Nice Lady?

I wanted my special to be full of really good jokes, and I think I accomplished that. You hear a lot about women in comedy, and I do talk about a lot of female things because I am a woman. But I just wanted it to feel like a good comedy special, like anyone could watch it, kind of burning down the stereotype of, “This is what a female comedy special has to look like.”

On your 100-show tour, what exactly was the process when it came it refining your material?

I definitely agonized over it a bit. I had all my main jokes on index cards, and I was trying to organize them into the order that I thought was most logical and had a good arc to it. At that point I had about 20 extra minutes, so I had to decide which jokes I was going to take out. There were definitely some jokes where I was like, “This joke isn’t ready, this joke’s too old.” [Eventually], I was like, “All these jokes are really relevant, they’re all strong, they’re all finished. They all have a beginning, middle and end.” But it took a lot more than I even thought it would.

There’s a degree of vulnerability that comes with stand-up, as with any kind of live performance. It must be daunting going out to tape a special, knowing that things can go wrong and you may need to recalibrate in the moment.

I think that’s where all those hours of club dates come into play, where you don’t know who you’re going to have in the audience that night. Some people might be fans of yours, some people might have gotten a free ticket off the radio and they might absolutely hate what you have to say. Or they might be drunk, or whatever the lovely combination of scenarios could be. But you learn through practice how to deal with that kind of thing. I think stand-ups are particularly good with hecklers and things like that.

One of the other reasons I wanted to do the jokes so many times is I wanted to make sure they worked everywhere. I don’t like performing just on the coast; I love going to the middle of the country. I love making sure that everywhere I go, this joke works, that it’s worded in a way that everyone can grasp onto. I think when you’re on stage and you’re telling a joke for the first time, you’re very aware that it could bomb. You just have to have faith that if you keep working on it, maybe the next 50 times you say it, one of those times you’ll make it work.

HBO

Did you always envision the concept of the “nice lady” at the crux of your special?

You know, I don’t like naming specials. There was actually one night I was doing the hour at The Comedy Cellar and Trevor Noah came to watch it, and he was like, “You know what you should call it? Nice Lady. Because you say it several times throughout the thing.” That kind of reframed how I thought about the whole special because I was like, “Oh, that is the through line.” I had been saying it the whole time, I just needed an outside perspective to kind of show me that. I think women, they still want us in pretty little boxes sort of, and that’s clearly not who I am. So I thought it had a nice little thesis statement in it.

How did the experience of working with Noah and Seth Meyers in the late-night arena strengthen your craft?

Working on Seth, I feel like that’s where I really learned how to write a good joke no matter what, because that was my first writing job. When you first get into comedy and you’re writing stand-up, if you’re in a bad mood or something, you don’t have to write that day. My first writing job at Seth, I was like, “Oh you have to produce no matter how you feel.” Your brain could be fried, you could be mad, you could be sad, you could be very happy; no matter what, you have to produce jokes that day. He has kind of a high bar for jokes, so it really helped me become a much better joke writer. Also, since he’s a straight white man, there was nothing to lean on with him. I had to write a joke that was just a good, well-worded joke, so that helped a lot.

Then with Trevor, I learned a lot about performing. Trevor’s an incredible performer and he taught me a lot about pacing, and volume, and engaging the audience, and not being scared to have pauses and silences. So it was actually two really great people to work with because I learned such different skills from both of them.

You really went for the jugular at this year’s White House Correspondents’ Dinner. Could you discuss your intentions heading to this appearance, your experience of the room and your reflection on that night in retrospect?

I spent all of April working on it. The funniest part is, I must have done this set 40 or 50 times at The Comedy Cellar and it never got leaked—which I mean, thank God. I had probably twice as many jokes as I ended up telling, and I kept cutting through and reorganizing it. I wanted it to feel like it had a beginning, a middle and an end, and I didn’t figure out until that last week that “Trump is so broke,” and tying it in with the media. I was really happy when I was able to make that come full circle.

The night of, first of all, I realized why a nice suit is good—a nice, well-fitted suit. I was like, “Oh, I feel amazing in this. I know why men have been doing this for a while.” [laughs] I had a lot of comics texting me before; one of my friends texted me and he was like, “Remember, if the audience is cringing, you’re doing well.” I just remembered that as I was telling the jokes, and that really helped me sit in those moments and be calm and be like, “Right. Again, this isn’t for them. This is for everyone at home.”

Michelle Wolf
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Ultimately all I wanted was to write good jokes that other comedians would look at and be like, “Those were good jokes.” Because that’s all you ever really want. You want the respect of your peers. I was very happy with the result because it’s not the time to play nice, I don’t think. If it was Obama era, those jokes would have been totally different. But these aren’t the kind of people that deserve fun, silly little jokes aimed at them.

What did it feel like to be called out by President Donald Trump himself? Did you consider his barbs a badge of honor?

I would be very offended if the President liked my comedy, although I’m not sure he laughs ever, which is very disturbing. But the thing I would say overall, that was the best thing, was the response from other comics—everyone from my friends to [David] Letterman and [Dave] Chappelle, people that I’ve admired my entire life. It was so heartwarming; I was over the moon.

At the dinner and since then, you’ve been as hard on the media covering Trump as you’ve been on Trump himself. Was calling them out always the intuitive move?

I’ve been deflating what the media’s been doing since Trump announced his campaign, and they had cameras pointed at those podiums before he came down the escalator, for like an hour. I think they’re grossly mishandling everything, and I wanted to point that out because they’re not the news. They’re entertainment, and they’ve distorted how people look at the news. I think it’s really bad for society. It’s hard to go to a place to be like, “Okay, I’m going to get my news here.” You really have to work to seek out where you find actual news.

It’s one thing to report on something, it’s another thing to involve four different people to have a conversation about it over the next 12 hours. [laughs] You can report what Trump tweeted, but you don’t need to discuss it for three days, especially the little stuff. Like, there’s actual, legitimate problems, and then we’re discussing Omarosa for a week. It’s like, “Come on, we’ve got problems. Let’s talk about that. We’ve got to keep our focus here, guys.”

What has this last year of your career taught you, and what are you looking to do as you go forward?

What I learned this year, especially with both the special and the dinner, is just no fear. Never have any fear. Go out there and trust your jokes. As my friend gave me a note before I went into the dinner, “Trust your jokes. Burn it to the ground.”

I was just on tour with Jon Stewart and Chappelle in Atlanta, and watching both of them, they take so many moments to be quiet, and slow down, and tell a story. I’d like to get better at that, trusting my presence on stage and that the audience will go with me. So that’s something I’m really looking forward to working on for my next special. Man, I can’t wait. I can’t wait to do another one.