Interview: Whitney Cummings

Whitney Cummings might be the busiest woman in entertainment. Not only is she in the middle of her latest tour, Big Baby (Details & Tix), but she is also a regular guest on Hollywood Squares, guest judge on RuPaul’s Drag Race, host of the Max TV show, Fast Friends, and host of her podcast, Good For You, but maybe her most significant change of all is motherhood! In advance of her tour coming to Cleveland’s Agora Theatre this Friday (February 28th), Cleverock had the opportunity to catch up with Whitney before her show.

After pointing out her slew of projects and commitments and how Whitney manages to balance them in her life, Whitney was asked what keeps her inspired and motivated to stay awesome on so many levels.

“A deep fear of failure and of desire to get my dead father’s approval,” she said. “I don’t know. The way you say it does sound like a mental illness, so you know, at least I have one that will pays my bills!”

It’s not always easy to say ‘no’ and pass on an opportunity. Still, Whitney touched on how the business has changed and how diversifying her exposure has helped her navigate the ever-changing industry.

“Yeah, it’s a tricky one,” she admits. “You know, the business has changed so much, and all I really care about is doing stand-up live for people and tour. It’s getting harder and harder to tell what gets people to know you’re in their city. You know? So I think for me, I try to go all out. Let me do just everything.”

“I’m hoping that I don’t go do a show in Cleveland, and then on the way back to the airport, half the people at the gate are like, ‘Whitney Cummings?! What are you doing here?’ and I’m like, ‘I was here last night! How did you not know that?’

“I think the hardest part now is just going like, OK, we’ll do some network TV. We do some Hollywood Squares, some podcasts, and some Rogan. You hope something will stick. All I really want to do is be in the same room with a bunch of people who are strangers, but don’t feel like strangers, and that is the only thing that keeps me sane at this point. You go online, and you’re like, oh, everyone hates each other, and everyone’s toxic. Then you’re like, no that’s the Internet, when you get in a room with a bunch of people and no one knows who the other person voted for. No one knows who everyone else is, and they’re all shoulder and shoulder, laughing at the same stuff; you’re like, we have so much more in common than we don’t! We’re not that divided. If you go to a comedy show, you’ll see that.”

She’s not wrong. The world IS a toxic place right now (literally and figuratively). Most days, people don’t want to even look at the news. They especially don’t want to look at commentsand sections on social media and get more upset. Considering that everyone at a comedy show is just there to have a good time, including the comedian, there’s so much more to enjoy with one another.

“I think that we’re at a time where we’re all in our custom algorithms, we’re all getting news that we kind of asked for in a way. We’re in our bubbles, and I just don’t know. One of my favorite things to do is go hear someone talk that I might not agree with or who says things that I’m not expecting? I think that comedy is more fun than ever, certainly, because there’s danger again! You know, people are getting offended and they’re getting upset. By the way, we love that! You know, we comics didn’t sign up to be beloved, we signed up to be polarizing! You love us or you hate us,” Cummings said. “Usually, if you hate us, it’s more about you than it is about us. It says more about them than us, you know. I think comics are more like a Rorschach test! I think it’s just so cool, I mean of course I want people love me. Of course, I want everyone to think I’m funny, but you know I think that to me good comics, will make you laugh and make you think. Try and piss you off and then make you laugh again and then give you an insight you haven’t thought of before . Then make you laugh.

“I think that people on the Internet are killing comedy,” she continued. “People don’t come to comedy shows as much anymore ’cause they can just see it all on the Internet, but you know, I think that you because we’re all waiting in this toxic cesspool of like misinformation. But comics, we only care about what’s true, and when you can go, ‘Oh, that’s so true!’ And share reality, I think that’s what gets us all through life.”

This is absolutely true about comedy. Cleveland has a wonderful comedy scene, and anyone in Cleveland can find comedy on any night of the week. It’s important to remember that once seated in the club (and hitting your two-drink minimum), everyone is there for a good time. Sometimes, that challenges the audience, and sometimes, it brings people together.

In addition to Whitney being one of the busiest women in the industry, she recently added motherhood to her list! Whitney talks about her balance, both in life and in her show, that becoming a mother has changed for her.

” I just really don’t want anyone to not feel like they can come to the show because they don’t have kids or they have kids, and they don’t wanna freaking hear about them even more! You know, ‘I have to see my kids all day I don’t wanna hear about someone else’s problems with their kids! To me, becoming a mother, and if you caught me on CNN with my Roast of 2024, there’s a certain new bravery that comes with it and new clarity that comes with it, even if I’m not talking about having a kid. I think like I really grew up in public. I did my first special when I was 26 years old, it’s not that I don’t think those jokes are funny, but I’m such a different person now. I think that all the people that liked me back then, I think they probably matured faster than me. When I was 35, single, a mess. Everyone’s like, ‘Whitney! We’re married with kids. Let’s get it together!.’ I’m excited to just catch up,” Cummings said. “You know, in terms of maturity and having my eyes open about things that I probably didn’t before. When you don’t have a kid, you can be a selfish ball of narcissism. You think you’re the most important person on the planet, and I also kind of hated myself. Plot twist: I guess I’m not a malignant narcissist because, before I had a kid, when I thought about myself all day, I hated myself, but now I only think about myself for an hour a day like I’m kind of like, I’m cool! So there’s this level of self-loathing that has been removed from my work that has opened up so much space for me to be able to really think more deeply about other things and not make it about me. I’m really proud of that. In comedy and some of the best comedy sort of tells us what we should care about, you know and I think that before I had a kid, I wasn’t capable of caring about the right things, and that’s just me personally, but whether you have a kid, or don’t have a kid, the show is gonna be equally as fun! I’m never gonna make it just about being a mom. And, of course, you know, I’m white trash ’til I die. I’m not with the father of my son. Of course I did it all imperfectly, and, you know, I’m really excited to talk about the new insights I have from being a parent and not just only talking about my kid.” 

Typically, having a child does change people. It really should! Kids don’t come with an instruction manual and need complete support. Sometimes, the way it changes is a person is very outward, and in other ways, it’s internal. When it comes to comedy, like most of life, there should be a balance of stories and routines that are affected by this life change. Those can be the best stories, even if an audience doesn’t directly relate. Whitney has not only met that balance but even found a new sense of positive self-worth while being an awesome mother to her son. She provided a few more examples of her self-improvement due to motherhood.

“Yeah, you also have to make some changes, like I stopped getting Botox once I got pregnant, and I haven’t gotten it since. I also stopped smoking weed, like I’m sober now. I mean, there are just so many things changing in my life afterward,” she explained. “Having the kid is almost the least big change, in a funny way! The way I get my news is different now. The way I think about people that vote differently from me has changed. There’s a new level of compassion. As someone who is known as a ‘roast comic,’ I’m always pushing people. Having a kid really, I don’t wanna say it’s softened me, but it kind of really made me have this deep level of compassion that is hard to have these days, and it’s helped me see things that I think way more unique and the thing matters most is in a funny or humor kind of way. Then a lot of times, you’re like, the humor that comes with being like, ‘Wait, I have a kid?’ I’m still a kid! Wait, what? lol. Wait, what like, i’m responsible for this person. I think that a lot of people probably relate to that on some level as well. Especially with how quickly you just have to get your shit together and just try to mature as fast as possible so that you don’t go to jail! Like I could go to jail. If I don’t figure this out lol! You know the stakes are so high! I can’t be Snapchat while I’m parenting my kid. There are just so many things that I that I think I do well when I’m being told something is how it should be, and then I kind of pick that apart and put it in context, so when people like you, how could you put your baby on social media? How can you put pictures of your kid on social media? I feel like it’s a little better than what happened when we were kids! There was take your daughter to work that they would bring us to their job and show us off in person. Their  coworkers know I thought that was weird that I was just like in my little school dress and just hanging out with adult men in their office, watching them work! I think for me, I like to kind of put things in context. When everybody’s freaking out, I think comedians do a good job. You know if we’re doing our job right at making you panic about things you never would’ve worried about and then putting you at ease at the things you were worried about,” she said with a laugh.

Whitney Cummings is a woman who is more popular than ever and isn’t slowing down anytime soon. Motherhood has changed her in ways that she seems happy about, which is refreshing to hear. Comedians have dedicated their lives to doing something that brings many people happiness and joy. The only thing better is for an audience to see and know that the comedians themselves feel the same! Whether you have a child or not, Whitney’s show this Friday is for you! You can expect to see her classic witty self in Cleveland and at The Agora Theater this Friday, February 28!