Whitney Cummings on Her Directorial Debut, Internet Trolls and Roasting Trump

Whitney Cummings was right around 30 when her mother and father suffered strokes within two years of each other. Desperate to understand what went wrong, she began devouring neurology books, which led her to Louann Brizendine’s The Female Brain. While it would do little to aid her parents, the book profoundly changed the comedian’s understanding of herself. “I remember feeling an overwhelming sense of relief,” she says, “and a lot less crazy.” Now Cummings, 35 and a prolific TV creator (2 Broke Girls, Whitney), has spun the tome into a pop-science rom-com (out Feb. 9 via IFC Films), enlisting Neal Brennan (Chappelle’s Show) to co-write and lining up Sofia Vergara, James Marsden and the NBA’s Blake Griffin to join her onscreen. That her directorial debut, a film centering on empathy between the sexes, arrives in the heat of the Time’s Up moment isn’t lost on the D.C.-reared Ivy Leaguer, whose current resume also includes a warts-and-all memoir (I’m Fine … And other Lies) and co-showrunning duties on ABC’s Roseanne revival. Though the movement has Cummings reconsidering some of her early experiences in comedy (more on that later), she says stand-up remains “the only place I’m comfortable.”

Your financier, Black Bicycle’s Erika Olde, had to persuade you to direct The Female Brain. Why?

I wrote it with Neal Brennan, and we were trying to get financing. The indie movie world is like a bad Tinder date, and there are always strings attached. There was one financier who was like, “We love it, but we want more nudity.” And I was just like, “Red flag!” I mean, I took five meetings, don’t get me wrong, I tried to make it work, like any bad relationship. (Laughs.) But then we found this young woman who’s really passionate about making films with female filmmakers and giving them opportunities, and we sat down for lunch and I was like, “Great, let’s figure out who’s going to direct it.” And she says, “Why don’t you direct it?” And I was just like, “Mm, I don’t know…”

Why the hesitation?

There are tectonic plates moving in our business but — and this is my shit that I need to work on — I still have a bit of shame around raising my hand and being the boss. Our society has this way of going, “Don’t shine too bright, know your place.” So the idea of being in a position of domination made me [uncomfortable].

By 28, you had already created two TV shows. You didn’t get comfortable then?

I definitely learned, but there was also a bit of, “She’s doing too much and we don’t like it.”

Who’s the “we”?

My @ replies on Twitter? (Laughs.) There was a bit of, “Who does she think she is?” And people get mad at you. I thought my dreams were coming true, then someone was like, “Don’t listen to them.” I’m all, “Who’s them?” I had no idea. I do think things have changed, even in the last six months, but there’s this idea of, you don’t get to achieve too much [as a woman] without losing friends and people not liking it. And I’ve definitely had male counterparts [for whom] people were like, “Fucking awesome, dude, that’s so cool. You’re killing it.” There’s not a lot of, “Who does he think he is?”

You’ve turned a nonfiction, pop-science book into a romantic comedy. What was the appeal for you? 

I’m at a place in my career when I really want to make the kind of things I wish had been available to me when I was 20. It’s what we were trying to do with Two Broke Girls. Michael Patrick King and I saw this void. There were all of these women in their 20s on TV and their stories were all, “Is he going to text me back?” And we were just like, “Who are these girls? These are not my friends.” All of my girlfriends are trying to start businesses and are running blogs and they don’t give a fuck if he texts back. 

You act, write, direct and do stand-up. Where are you most comfortable?

Stand-up. It’s the only place I’m comfortable. In this business, it’s a lot of make-believe and pretending and fake on-camera hand-offs, and you’re in the bullshit meetings and you’re just like, “Great, let’s have a drink.” We’re never talking again. And onstage, the truth is so valued that it’s where I oxygenate and it’s where you’re able to go validate your reality.

And, presumably, develop a thick skin?

Oh yeah. I need to work on my feminism, if you will, because I’ve gone so numb from the amount of rejection you get and how tough you have to be to withstand it emotionally, I didn’t realize some sexual harassment I had dealt with. I’m so dead inside that when I see some of these accounts come out, I’m like, “Oh, no. Like, is that …?” I now realize that was not OK.

Have you tackled all of this on stage?

Yeah, I’ve been at the Comedy Store a lot because when things like this come up, comedians just need to work it out, and I really wanted to figure out: Is this universal? Is this just a Hollywood thing? What is this? But it’s tricky. The other night, I started going into this area about women confusing empowerment and entitlement and it got awkward. People think, “Ooh, we can’t laugh at this stuff,” but we have to talk about and laugh at the uncomfortable stuff, too. One of the big conversations I’m trying to have onstage right now is that to be pro-woman, you don’t have to be anti-man. Saying all men suck makes you look like an idiot. And it’s not helpful.

You got your start writing for Comedy Central roasts. In 2011, you roasted Donald Trump.

Yep, I spent seven minutes on TV talking about the president’s penis. (Laughs.) With every roast, it’s all fun and games until you’re up there, and then people’s feelings always end up getting hurt. But his feelings did not get hurt. I remember being like, “Wow, he’s loving this.”

And net-worth jokes were off-limits?

Oh yeah. At every roast, something’s off-limits. I love that it wasn’t his daughter or his wife, it was his money. (Laughs.)

You don’t see a lot of those televised roasts anymore. Why do you think they went away?

I have a theory, which is that the idea of a roast is to go to this forbidden, uncomfortable, almost performance art–level shock place, but because we’re so regularly shocked and offended today the idea of an hour and a half of unbridled negativity is just so unappealing. We almost need the opposite now: an hour of unicorns and compliments.

A version of this story first appeared in the Feb. 7 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.