Chapter 95: Bess Kalb on kvetching over koans and kindling comic kinship

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“Why are women, who have the whole male world at their mercy, not funny? Please do not pretend to know what I am talking about.”

So begins a 2007 Vanity Fair article by Christopher Hitchens called “Why Women Aren’t Funny”.

College student Bess Kalb picked up a copy of the magazine, read it on her train ride from New York to Rhode Island, and, in her words, “became radicalized.” She decided then and there to drop out of school and become a comedy writer. She scored an internship with The Colbert Report and then (“because I’m an anxious Jew who is the daughter of two anxious Jews”) went back to finish her degree before working for Jimmy Kimmel for eight years. (And scoring a few awards while working there!) She then puts out a “ghost memoir” in 2020 called Nobody Will Tell You This But Me which becomes a big New York Times bestseller and ranked one of the best books of the year by Vogue, Forbes, Wired and others. (Jodi Picoult said “I have not been so profoundly moved by a book in years.”)

Today Bess Kalb is 34 years old. She lives in Hollywood with one kid and another on the way. And she is a truly prolific comedic genius. She’s been nominated for an Emmy and a Writer’s Guild Award and has also written for The Academy Awards, The Democratic National Convention, and her incredible special Yearly Departed (where she is Creator, Executive Producer, and Head Writer).

Do you know Yearly Departed?

Leslie and I loved it. You can stream it on Amazon Prime. (2020 or 2021!) Bess came up with the idea of developing a comic sendoff to 2020 with a mock funeral featuring female comics, each coming onstage to give short eulogies to parts of the year. Tiffany Haddish shows up. Sarah Silverman shows up. Dulcé Sloan shows up. Jane Fonda shows up. It’s a huge hit and she pulls it off again in 2021. It’s fresh and funny and creates wonderfully necessary sign-posts as we navigate the (hopefully?) tail-end of this horrible pandemic.

With the brilliant full moon above our heads let’s sit down with the equally brilliant Bess Kalb to talk about: how we keep anxiety at bay, how we help dismantle celebrity culture, what is one way to define success after making it up the ladder, how might we think about “diversity hiring”, what gender norms are baked into the comedy that we consume, what is a structurally perfect joke, what might a fake male virtual assistant buy you, and much, much, more, including the amazing Bess Kalb’s 3 most formative books.

Let’s flip the page into Chapter 95 now…