Comedian Whitney Cummings Talks Sex, Podcasts, and Power

Photo courtesy of Ridgefield Playhouse

Fresh off her role in the film How It Ends, comedy megastar Whitney Cummings sat down with WM before taking The Ridgefield Playhouse stage on Oct 8 and 9.

You’d think that after several hit films, an eponymous TV show, a book, and four comedy specials, Whitney Cummings might rest on her laurels. Think again. Hot on the heels of the July release of her costarring turn in the Zoe Lister-Jones’ film How It Ends, the creator and host of the Good For You podcast is stopping by The Ridgefield Playhouse on October 8 and 9 for two nights of searing standup.

According to Cummings, her more recent work marks a clear evolution in style. “For comedians, a lot of times the approach is: ‘I’m right, and I am going to dig my feet in.’ But, for me, the goal is to look back at old specials kind of like you look at old pictures of yourself from the ’80s, like, ‘Ugh, those bangs were not working!’” says Cummings with a laugh. “I look back and think, I am such a different person now, which is good. The idea is to get new information and then change your mind.”

According to Cummings, some of this change is due to a shift in her perspective as to what it means to be a woman in the world of comedy. “In my early standup, I was so used to being one of the only women in a male-dominated field that I thought I had to be really aggressive and shocking and sort of neuter myself [in the process]. I didn’t feel like I was taken seriously and that I had power, so I had to do the kind of things that indicated power,” explains Cummings, who is also the creator of sitcoms Two Broke Girls and Whitney.

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Photo courtesy of Ridgefield Playhouse

“There is this conversation about what we can say and what we can’t say [in comedy], but for me, as a woman, the most taboo things to talk about have always been being powerful, having money, being a boss, and enjoying sex,” shares Cummings. “In the beginning, I think I was always minimizing that stuff because I felt it was my job to make people comfortable … and it just never made any sense. I’m finally at a place where I feel so comfortable onstage that I don’t have to address the ‘woman’ thing anymore. I don’t have to prove to everyone that I’m strong. I don’t have to neuter myself.”

Apparently, this outlook is paying off, as Cummings just played the hilarious host of a party held on the dawn of the apocalypse in the 2021 film How It Ends. The flick has drawn some critical acclaim since its July release on Amazon Prime. Cummings notes the movie “is the perfect combination of wildness and off-the-wall comedy but also pathos, and it’s really cathartic for everyone who’s going through the idea of Who am I? after this pandemic.”

Cummings brings a similar energy to her podcast, Good For You, which has already welcomed big-name guests, like Paris Hilton, Alison Brie, and Kaley Cuoco. “It’s part late-night show, part interview show, and part documentary,” says Cummings. “We are almost at a hundred episodes, and it took me like 90 episodes to figure it out. I’ve had to face a lot of my own insecurities, and every episode is wildly different, as well. It’s not like any other podcast; sometimes it’s jokes the whole time, and sometimes it’s talking about BLM the entire time.”

When it comes to her comedy, Cummings points to apps like Instagram and TikTok as the future. “Social media is this new opportunity to make something kind of special and weird, whether it’s two minutes or 10 minutes, with no notes and no pressure from advertisers,” she says. “On my IGTV, we make all these super-cool videos that we recut and then people get to share and connect. So, I am really focusing, believe it or not, on these short-form comedy pieces. Even on TikTok, it’s almost like you are Charlie Chaplin again. You are making these little silent films, and there is something so fascinating about that.”

Yet, just before the conversation ends, Cummings suddenly pauses to reflect on a moment from her past that motivates even these cutting-edge comedic efforts. “I remember when I used to go to Broadway shows when I was a teenager. I went to see Rent for the first time, and I was just transformed as a person,” Cummings recalls. “I obviously can’t sing and don’t put on musicals, but I thought, I want to give this feeling to people that this show just gave me.” Considering her raft of accomplishments and millions of social media followers, it may be safe to say Cummings has been successful in that endeavor.

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