Whitney Cummings launched her career by making fun of Donald Trump's flaccid dick (among other things).EXPAND
Whitney Cummings launched her career by making fun of Donald Trump's flaccid dick (among other things).
Jill Greenberg

Whitney Cummings Delves Into the Dark Stuff Beyond Donald Trump Dick Jokes and Sitcom Stardom

Six years ago, Whitney Cummings was on the brink of major mainstream success. Two shows she created — Two Broke Girls, co-created with Michael Patrick King, and her eponymous sitcom Whitney — had just premiered on major networks, thanks to her early success doing stand-up on late-night TV and appearing on Comedy Central roasts. One of those was the 2011 roast of then-buffoonish businessman Donald Trump.

“I think it should be a general rule that if you’ve been on a Comedy Central roast, you shouldn’t become president,” she quips over the phone ahead of the release of her new book, I'm Fine ... and Other Lies (Penguin Random House, $27), and a three-night stint at Largo. “I made jokes about his flaccid dick and now he’s our president, and now I have to live with that. The joke is on us, I guess.”

Even at the time of her introduction to a wider audience, the comedian was suffering from a severe crisis of confidence. With Whitney floundering (she says she should have done a multicamera show on CBS and the result could have been more promising), Cummings had to learn quickly and at a young age (she was 29 when it first aired) how to be the boss of the show. She often found herself in uncomfortable situations — including giving critical notes and firing staffers.

“Everybody hates the boss no matter how nice you are,” she recalls of running the show. “It was completely the opposite of what I was trying to do, which was getting people to laugh at you and love you. Being a comedian and getting your own show is very challenging because of the motive of what gets you into comedy in the first place and to have high tolerance for other people’s discomfort, which I didn’t have.”

In what could have been a precursor to today’s culture wars, having a loud, successful female lead wasn’t what people were looking for in a network sitcom. If dealing with corporate pressures served as a check on her success on a macro level, she was dealing with a number of personal issues that plagued her for years as well.

“I really tried to do this disruptive, subversive thing,” she says of Whitney. “I tried to do a gender reversal where Chris D’Elia’s character had all of the traditionally female characteristics of being calm, collected and settled down. Mine had the male qualities, which were reckless, commitment-phobic. To see the same stereotypical characters over and over again seemed to be insulting to viewers.”

Contrarily, 2 Broke Girls became a hit and ultimately landed in syndication. Dealing with the failure of Whitney and subsequently E!’s Love You, Mean It With Whitney Cummings — “I thought I was going to do this incisive show with like Michael Moore and Malcolm Gladwell; instead I got Snooki," she says — forced her to re-evaluate what success meant to her.

“What’s the point of having a show on the air if you don’t believe in [it] or are miserable?” she says. “I realized doing the wrong show is way worse than having no show because you feel fake and phony. It’s a terrible feeling.”

Throughout her turbulent television career, Cummings continued to journal and write about things she tried to make sense of in her life. She didn’t know it at the time but those entries would become the blueprint for her first book. In I’m Fine ... and Other Lies, she chronicles — albeit with her trademark sharp humor — low self-esteem, a severe eating disorder and professional ups and downs in a fashion that feels removed from her acerbic stage persona.

“Writing the book was a nightmare,” she admits. “It was a truly harrowing experience to say the least. I thought [that] since you hear all these romantic stories about writing a book that it would be great. Then, you remember that most of these authors had clinical depression or were alcoholics, and you get it. These are all of the stories and material that I never felt comfortable talking about onstage because I was too embarrassed and didn’t want to say this stuff while making contact with strangers. It was definitely the hardest thing I’ve ever done.”

The book may be hitting shelves today, but writing — especially humor writing — has been Cummings’ coping mechanism since she was a teen. Her tough persona made writing about her insecurities and darker moments a challenge, but she decided that if she wrote about her demons in this manner, maybe it would help others feel better and get help.

“In my late 20s, I realized being crazy isn’t cute in your 30s and I couldn’t stop,” she says. “I knew I had to get ahead of that. Although the stories are really dark, I do come out all right on the other end. I found that when I was trying to not be crazy, hearing about other people's trials and tribulations with mental health issues, eating disorders and addiction made me feel better.”

After a couple more stand-up specials, Cummings is now the executive producer and a writer on the Roseanne reboot. Similar to how 2 Broke Girls presented what's like to be poor, young and living in a big city in a way that resonated with people, putting Roseanne back on the air, she says, is a way to get a middle-class family back on TV.

As she hits the road with a bunch of friends including Neal Brennan, Cummings' shows are going to revolve around her new book. The tentative plan includes podcast-style "In Conversation" types of shows, and will continue that way depending on the audience’s enthusiasm. But once the tour is over, Cummings is going to tape another hourlong special and return to a much-changed TV landscape that could be more receptive to a powerful female lead.

“I’ve spent so much of my life hiding my flaws and weaknesses because I didn’t think anyone wanted to see them, and I was embarrassed of them,” she says. “It made me realize that people don’t just want funny. With so much on going in the news right now, and so many people in a lot of pain, I don’t think people want jokes and me to only talk about my bad relationships. No one is talking about mental illness, and it’s comedians that are pushing the envelope and talking about something that people are pretending isn’t happening.”

Whitney Cummings' I'm Fine ... and Other Lies Tour, Largo, 366 N. La Cienega Blvd., Beverly Grove; Mon.-Wed., Oct. 9-11; $50 (with book and meet-and-greet). largo-la.com/event/1522513-whitney-cummings-i-m-fine-los-angeles.

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