The Chatroom: Whitney Cummings

Plug your headphones in, pretend you’re doing work and WATCH!


You need excellent eyesight to be a good comedian. In order to connect with your audience, you have to see the world as they do. To make them laugh, you have to see what they’re seeing but from a new point of view. To make them walk away repeating your jokes and quoting punchlines to friends because they never thought of it like that before, you have to hang upside down from metaphorical trees, use a telescope, get awkwardly close.

And timing. You need good timing.

Comedian Whitney Cummings has 20/20 vision — she’s also quick. She’s insightful, introspective and extremely funny. (That last one is important if you’re a comedian.) In this episode of The Chatroom, the writer of Two Broke Girls talks to Leandra about what it takes to hold an audience captive, the importance of authenticity and how thinking about fashion made her a better writer. It’s an interesting way to see Cummimgs from a different angle, which is key: to really entertain a group of people, your audience needs good eyesight, too.

Visit Whitney’s website and follow her on Instagram and Twitter.


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  • I love these videos. Although I have to admit that since it seems to be the same content as Oh Boy what they talk about isn’t exactly new. But I like seeing Leandra and Whitney talking nevertheless! I frankly find Leandra to be a really good interviewer/conversationist. Really intellectually stimulating.

  • Fanette Guilloud

    I think it’s one of the first Chatroom where Leandra is speaking so little haha. Nevertheless very interesting discussion as always. Particularly love all the “you can talk about a skirt/fashion and just immediately after start discussing psychology and self esteem… and still be respected”. It’s getting better today but I (personally) still feel that guilt emerge when talking seriously about frivolous things such as make up or fashion. And honestly the best discussions I have with my friends are a mix of both these frivolous things and more serious/psychological/down-to-earth ones. So let’s keep doing that shall we

    • Aydan

      Yes, as with everything else in life, its all about balance! But damn girl speaks the truth!!

      • Marlene Gallant

        When I saw the draft of 5436 dollars, I accept that my friend’s brother was like really generating cash in his free time with his PC. …yh His aunt’s neighbor has done this for only 10 months and by now repaid the loan on their home and bought a new Car .

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  • Amelia Diamond

    I have told so many people that SATC story after hearing her tell it

  • Merillionaire

    Yeah, is this not the video that accompanies the Oh Boy! audio?

  • That was the fastest 6:45 of my life. And Leandra, THAT BLAZER.

    • Kate

      Yes! More details on that outfit please!

  • Does Whitney Cummings ever shut the f^%* up?

  • LJIS

    Yay Whitney. Keeping it real.

  • bloom a glow

    so interesting learning about the characters and their relationship with fashion and love the SATC story