Whitney Cummings Dares To Take On Pollstar Awards & 2020 Theatre Tour

Whitney Cummings: I hear that’s going to be a real mess. All the comedians that have done it, they’re like, “People are drinking or partying. Good luck.”  

Everyone says it’s a rough gig.

The business is changing so much. When I started it was all about doing television, all about getting a sitcom. The power is sort of moving away from the television networks and the executives into the hands of the performers with social media – and they don’t need 10 lawyers or executives to decide when they get to connect to their fanbase or not. So that has made live touring so much more exciting because you know where people like you, you know in what cities people want to see you. … 

Now it’s like you’ve been Googled this many times in Tampa, let’s do a show there. And let’s do a show in Toronto – that’s where most of your merch was sold. 

Not everybody’s got Hulu. Not everyone’s got HBO Max – but everyone has a theater in their town or a comedy club in their town. And I find that the more TV shows there are on the air, the more people want to go see live comedy. We’re on our phones all day. I think sometimes when people get home they don’t want to look at another freaking screen.

Comedians right now are feeling this disconnect between what Hollywood wants and what America wants. Everyone’s scared to say certain things and scared to offend people and scared to be risky. But America doesn’t want that. They want to hear something crazy. They want to hear a funny take on something. They want to get offended or roasted or whatever. … Audiences have more of a sense of humor than Hollywood. So I think comedians in particular are like, “You know, we just want to go out there and do what we do and not be told what to say and how to say it.” And so I think that touring is very necessary for comics right now.

Look, I think that part of my job as a comedian is to play devil’s advocate. And also to point out hypocrisies. That’s what comics do. And I think that comics always know that two truths can exist at once and that not everything is binary. Not everything is right. Not everything is left. We play in the gray area and I think that’s part of why going to see comedy is so important right now. 

We’re coming for everybody: the right, the left, the middle. We’re the ones that poke holes in everything. And I think that’s where the comedy comes from, is that tension. … I think that it’s important that we point out things that are ridiculous. Even within important moments of progress. You can have progress and still criticize the progress.

But you know, I will say in the new tour, I don’t talk about politics at all.

There’s so many ways to get jokes now with Twitter and memes and Facebook and “The Daily Show” and late-night shows. And so by the time you come see a comedian, I just feel like people have heard enough politics. They’re on Facebook, they’re on Twitter all day.

I really pride myself on creating a comedy show where lots of different people with lots of different beliefs that might not have voted the same way can all get in a room and laugh about the same thing. Comedy’s supposed to be the great unifier.

I get everything from a bunch of guys coming with their office and sports teams all coming together to bachelorette parties to dates. My last special, guys came up to me afterwards like, “Dude, I just learned so much. Thank you. I’m so glad I saw that.” But I also get lots of women and girls’ nights. I don’t think about gender when I’m writing jokes. The idea is first to relate to as many people as possible.

Oh good! I think that women like when I make fun of men and the men like it cause I’ll make fun of women too. I think that it’s hard for men to make fun of women right now, but I think we have to be able to make fun of us.

I don’t know. I think everyone’s in a constant state of proving themselves. I think it’s hard for everybody to be a comedian because every night is a new night. You don’t get to coast on your success.  

You can ride your fame, your success for about two minutes. And then the audience is like, are you funny? Am I laughing? I just paid $50 plus two-drinks minimum, plus I got a babysitter for you. So I don’t really care what show you were on or what gender you are, I just want to be laughing.

Saying “I want more female comedians” to me sometimes feels like you’re saying, “I want more women to have bad childhoods.” (laughs) So I don’t want more children to be neglected, so they become funny. But I would like to see more female comics. I think it’s changing.  

I think that I’m a little bit spoiled or off base because I’m in comedy clubs every night and I see so many female comics. Whereas if you’re in your average town you’re probably only seeing a couple come through a year. But I see so many funny women right now. I think it is changing.  

Yeah, I think it’s changing because social media is democratizing all of this. … There are so many voices out there right now. With female comics I always say, normally you have to be really funny to get through. So if you see a female comic in your town, you should go see them. Because they probably had to work twice as hard and be twice as good to get where they are. We do quality over quantity.

I would say stand-up 100%. And I feel at home on my podcast because it’s [recorded] at my actual home. I’m still getting the hang of that, if I’m going to be honest. Podcasting is a very specific medium. I’m used to being a comedian where you have to be funny every sentence, but podcasting is more conversational. It’s a little more loose.

That’s true. For me [with] comedy, I’m kind of old school. I like very tight jokes. I like things to be machine-gun style. Rapid-fire jokes are less conversational – and podcasts are signified by how conversational they are. So it’s been a little bit of an adjustment for me.

Podcasting is almost like having a website at this point. You have to have one.  

It’s not enough to just once a year say, “Hey, come see me for 50 bucks.” If you’re not going to connect to people, someone else will. With YouTube and podcasts our job as comedians are really changing. I think our job used to be, “Hey, once a year I’m going to come to your town with an hour of jokes. I’ll see you next year.” Now it’s, “Between now and when I see you next year, we’re going to keep in touch.”

Oh, I heard that a lot. And honestly, if someone doesn’t hire me because I’m not pretty enough they’re entitled to do that. They’re the boss. I think that this is why I’m doing standup. I think it’s because I was like, you know what? I’m going to be my own boss. I’m going to do what I do. And then people can decide if they like me or not. I can’t force someone to hire me. 

And that was a time where it was very much only models were getting every part. And I am not that. And by the way, thank God I’m not stuck on some show. I realize now that I was dodging a huge bullet and that was doing me a huge favor.

For me, stand-up is the greatest thing in the world. And back to your question about why I want to tour, because I just want to make people laugh and entertain people.

There were so many weird barriers and rules and standards I couldn’t figure out because I didn’t fit in. And there’s always going to be boxes whether they are good or bad. And I think as comics we don’t like fitting in boxes. We like to grow. We like to evolve. We like to change our minds. We like to take risks and Hollywood doesn’t.

She’s a genius. She’s a legend and she’s always scared me. I’m still kind of terrified of her, but I have watched the way that she has built comedians with so much mindful strategy.

She is very delicate in the way that she makes choices. She’s the brain I wish I had in terms of decision making. I’ll deliberate over something till I realize I need to say no. And she’s like, “Yeah, no.”

She’s able to zoom out and see the big picture. She knows every venue, she knows the best way to route things, she knows markets. Most managers don’t do that. They want to go to Oscar parties and Golden Globes parties.

He’s such a legend because I think that people can trust him and he’s very thoughtful and he doesn’t put somebody in a venue before they’re ready. And he doesn’t try to bully people into booking someone before they’re actually going to move those tickets. His strategy a lot of times is, “I know you can play this size. So let’s play this size.” So then we add a show. 

And he doesn’t do anything out of ego. I’ve never met someone in this business that had a bad word to say about him. And it’s a business where people love to gossip and any excuse to criticize someone. He’s just gracious. He’s classy and comics love him. And comics don’t like anyone.  

As you get more known as a comedian, you have people that are coming specifically to see you. And when that happens, you get to play around more. You get to take bigger risks. 

When I first started, it was like, “I’ve just got to do the jokes that I know worked last time and just be funny.”  And now that people are coming to see me, that know me, I get to improve as a risk taker on stage and I get to do more ridiculous stuff because I know that if I fail, they’re going to forgive me and I’ll figure out a way to make it funny.

I’ve gotten more physical as I’ve gotten more fans because I get excited. I can feel the energy. I feed off of their energy and I feel like I can experiment more. 

When I was doing comedy clubs on these tiny stages, there’s only so much physical comedy you can do. And then when I first started playing theaters, I was like, “Oh God, I’ve got another 50 feet that I need to fill.” You need to go back and forth, you need to keep the energy up. I need someone that’s in row 50 to feel this as strongly as a person up front.