Q&A with Whitney Cummings '00

by St. Andrew's Episcopal School
One of the most recognizable names in comedy, Whitney Cummings ’00 has spent years making audiences laugh with her writing and performing. She took time out of her schedule to discuss her comedy, career, and St. Andrew’s.
You’re a comedian, writer, producer, director. Who have been your biggest professional influences and why? 
I have been very influenced by George Carlin, Richard Pryor, Joan Rivers, “Roseanne” Barr. I guess I really responded to sort of a voracious appetite for honesty and the truth, and digging into the little nooks and crannies of our psyche that are uncomfortable and embarrassing and shameful. I think that I get a lot of fulfillment out of doing that kind of thing, and I think that’s probably where I got it. It’s so oxygenating for me to receive the work of people who are brave and fearless enough to tell their truth and to admit humiliating thoughts or behaviors. And so I guess that’s kind of the route I wanted to go down as a comedian because I think that’s very healing for both the person enjoying it and the person doing it.
In terms of writing, Michael Patrick King. I’m a big fan of Norman Lear. In terms of making movies, I mean, endless. There’s so many people that inspire me every day. But I always love Sofia Coppola and Jane Campion and Patty Jenkins now. She did “Monster.” But now she just did “Wonder Woman” and I love that she can kind of do anything, that she did this drama about a horrific story, and then she did this triumphant superhero movie. I’m inspired by people’s careers that didn’t pick a lane, if you will. I’m inspired by people who, even if they have never done it before, decide, you know what, I’m going to switch gears and try this thing that I’ve never done before. And I think that’s sort of the people whose careers that I try to follow, the people who don’t limit themselves and don’t make fear-based decisions.
How have you evolved as an artist over the years and what do you believe has sparked that change? 
I think in the beginning as an artist, you’re just kind of doing what you think people want you to do, or you’re doing sort of an impression of someone that you like. So I think for me, I started writing just very, for lack of a better word, jokey jokes. I was doing the Comedy Central roasts. I was just kind of telling jokes. I was writing jokes and then telling them. I didn’t know at that point that anyone would be interested in who I actually am. I thought they just wanted to hear jokes, so it took me a long time to build up my self-esteem and understanding of myself and self-awareness to even be capable of doing that. So I think you have to evolve as a person in order to evolve as an artist. You have to stay curious. You have to stay hungry. You have to stay open and willing to be wrong and willing to explore really uncomfortable situations. So for me, as soon as I started being braver in my life, that’s when I became braver in my work. They say life imitates art. I believe art imitates life. But in order for art to imitate life, you have to have a life. So for me, I really had to work hard on curating a life and making time for the things that I could actually write about and draw from. So I think that I started growing as an artist when I started growing in my personal life. And then I think about things that make you grow as an artist that you don’t necessarily plan or want to happen. Pain sometimes can be very motivating, heartbreak, a death. I went through a really bad breakup and my dad died, things like that, that are horrific, not to glorify them, sometimes end up accidentally being something that really helps you grow as an artist because you figure out what’s important and you have to look at yourself in the mirror. And self-awareness, I think, is really a fundamental part of being an original artist.
You got your start doing standup. What inspires your material and performance style? 
It’s really just the things that drive me nuts and the things that get under my skin, things that bug me. A lot of people describe standup as people that have an obsession with justice. And I totally relate to that. The things that I think are wrong, the things that I think that are unfair, the things that hurt me and frustrate me, those are usually the things I talk about because that’s how I’m able to sort of work through my own feeling about them.
After years of performing and writing, you moved into producing with “Two Broke Girls” and “Whitney.” You recently starred, co-wrote, produced and directed “The Female Brain.” How challenging was this evolution/transition into leadership?
Being a comedian is a leadership role. When you’re doing standup, you are in charge of the 500, 1,000, 2,000, whatever number of people that are in the room. Your job is to make sure they feel safe and taken care of. You have to make sure that they aren’t worried about you. They need to know that you know what you’re doing. So I think that it was a natural transition for me to direct or produce because a lot of the job is just convincing people that you know what you’re doing, even though everything’s on fire.
And you have to just convince people that things are under control when they’re kind of not. So that is a lot of what the job entails. So it was kind of a natural transition. If you want people to work hard, you have to make sure they’re in an environment that they enjoy. And being a comedian and learning how to make people laugh is super helpful when things aren’t going well, to bring levity and humor and having a sense of humor about yourself and the high stakes nature of making a TV show or a movie, I think really helps everybody give their best, not be in fight or flight, and to enjoy the process, which is how you get good staff and crew. It’s by having a good reputation and not taking yourself too seriously and making sure people have a good time. 
You seem pretty active on social media. How important do you believe it is for artists to use your platform to engage in public on social issues? 
I don’t think we know yet if social media’s going to help or hurt, because it seems like there’s a lot of downsides to social media, especially around young people and being exposed to so much whatever it is, like celebrity and private planes and seeing your friends at parties that you weren’t invited to. I’d imagine social media would be very traumatizing if I was still in high school. Not that high school wasn’t traumatizing anyway. But at least I had AP history (with Mr. Whitman) to get me through it.
I think if you do have a following and if you do have a microphone, or a voice, or the power to get people to listen, or read, or engage, I think that is a responsibility. If you are a celebrity or have a lot of followers and you can remind young people to go vote or register to vote, I think it’s a little bit crazy not to. But I also don’t think people should feel obligated to do that. But I don’t know. The jury’s still out on social media. As long as you’re telling the truth and not spreading fake new, I think that as a celebrity, you’re probably in good territory.
What have you carried from your St. Andrew’s experience? 
Well, I definitely read the news every morning, which is something that Mr. (Glenn) Whitman drilled into our heads. We used to get The Washington Post every morning and we would read it. Links is a big one. I don’t know if he teaches that anymore. But Mr. Whitman used to make us always, when something was going on currently, we’d have to link it to something that happened in history that was similar, or put it into context. Which, now on a daily basis I sort of use that in my stand up because we do call backs. I do call backs in shows, which is like links in a way.
And I took a class that was ... What was it called? Crisis, something crisis, culture crisis. I don’t remember, but it was basically a class where all we would do is argue. And it really helped me develop my brain because that’s what being a comedian is. You’re kind of arguing with the audience about something. You’re arguing with yourself. You’re trying to present both sides and be fair and just. And sometimes put yourself in someone else’s shoes that you might not agree with, or take an unpopular stance on something and then defend it.
Being able to debate really smart people and present alternative views on something, that’s what I just sort of did on “Roseanne.” I was able to work with someone that voted differently than me and that was a skill that I think I definitely got early on from St. Andrew’s. Sure.
If you could go back 20 years and speak to your high school self, what advice would you give her? 
I would tell her, you need to work hard, but you don’t need to try hard. Does that make sense? Basically, I think it’s really important to do the work and to go the extra mile, so that when you arrive at your destination, you’re not having to scramble or overcompensate. Work hard with grace, not with desperation.
Busyness is a failure, not a success. It took me a long time to realize that. Being busy for the sake of busy does not mean that you’re important. It doesn’t mean that you’re interesting. It doesn’t mean that you are successful. Some of the most successful people I know actually work like five hours a day, and they work really smart instead of really long. And an absence of a life is not something to celebrate. Working weekends and until two in the morning is not impressive. It actually is sort of, you’re bragging about the wrong thing. It seems like a failure. Why are you so bad at managing your time?
Garry Shandling said this to me once: You can never make it too late if you’re an artist because you’re only going to get better. There’s no way you’re ever going to get worse as an artist. Just be patient and get good. Don’t try to make it early because if you make it too early, you’re going to get torn apart. And you’re not ready anyway. You might be ready for the money, but you’re not ready for the success and the fame and the feedback. It takes a while to get ready for that. 
Save your money. That’s another big one. Don’t spend it on stupid stuff that you’re not going to need or want in 10 years. Spend time with your family. I think when I was in high school, I didn’t realize how fast life goes, because you think in high school, “I hate my dad. I hate my mom. They’re so annoying.” They’re just the people that are stopping you from doing the things you want to do. But in fact, they’re everything, and before you know it, they could be gone.
Your teachers are smarter than you. I think when you’re in high school, you think you’re smarter than everybody. Then you get older and you’re like, “Oh gosh. I can’t believe that I tried to pull that off.” Of course my teacher knew that I was faking it, or lying about that, or that I pretended that I had done that work and I hadn’t. They knew. And a lot of the subjects that you think are a waste of time, I promise aren’t. Even if you’re not going to remember all the stuff from the class, your brain changes when you learn, and it grows. And it might be more about developing the skill to follow through than to actually retain information. 
Learn about neurology as soon as you possibly can. Your life will get better and more clear. That’s probably what I should’ve said first. Just start studying neurology immediately. 
I think that’s enough advice. I think my former self is annoyed by all the advice I’m giving her, so I’m going to stop.

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St. Andrew’s Episcopal School is a private, coeducational college preparatory day school for students in preschool (Age 2) through grade 12, located in Potomac, Maryland.