Wanda Sykes | Mike’s Dream Guest | Mike Birbiglia’s Working It Out
Wanda Sykes is one of Mike’s original dream guests for the podcast. Now, on the heels of her new Netflix special, Legacy, Wanda talks with Mike about how they both started in DC, and why Wanda left her job at the NSA to pursue a career in stand-up comedy. Wanda tells the story of how she moved from the writers’ room of The Chris Rock Show to acting in sketches, how she got tricked into auditioning for Curb Your Enthusiasm, and the weird requests she gets from Curb fans. Plus, new jokes from Mike and Wanda.
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Find Mike:
Website: https://birbigs.com/
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TikTok: https://tiktok.com/@mikebirbiglia
Find Wanda:
Instagram: https://www.instagram.com/IamWandaSykes/
Website: https://wandasykes.com
Hosted and Produced by Mike Birbiglia
Producers: Peter Salomone, Joseph Birbiglia, Mabel Lewis, Gary Simons
Sound Mixed by Ben Kruse
Supervising Engineer: Kate Bilinski
Video Consultant: Graham Willoughby
Special Thanks: Marissa Hurwitz, Josh Upfal, David Raphael, Nina Cwik, J. Hope Stein, Oona
Music: Jack Antonoff and Bleachers
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@rumigirl
June 17, 2026 at 7:45 am
"It's all of us…..that's the only way to fix this. It has to be — it can't come from one group. It has to be a diverse group of us." Such a loving, wise person.
@SparkleberryDreams
June 17, 2026 at 7:45 am
Why does she have to hate on Roanoke?!
@suzy3899
June 17, 2026 at 7:45 am
I love Wanda SO MUCH ❤
@koreakim693
June 17, 2026 at 7:45 am
Wanda's joke about lying to Jesus is one of the funniest bits I've ever seen, I still think about it all the time and it still makes me laugh even as a memory. Top tier comedian and great interview Mike!
@FallDamage004
June 17, 2026 at 7:45 am
40:30 How much do you think Mike donates each time on Working It Out For A Cause?
@TheOldHippiebilly
June 17, 2026 at 7:45 am
💜 WANDA SYKES ROCKS 💜
@debhil226
June 17, 2026 at 7:45 am
LOVE her!!! She is pure gold!!
@JoelWetzel
June 17, 2026 at 7:45 am
Wanda played Biggie Shorty in "Pootie Tang" and when she danced through her ringtone, all the way through that song, I was given one of my favorite movie memories. Thanks, Wanda.
@Leafers84
June 17, 2026 at 7:45 am
I love Wanda so much!! Great conversation Mike! My wife and I are really excited to see you at the Great Canadian Comedy Festival just outside Toronto later this summer. You, John, Nick and Fred are gonna make for such a fun night of laughs!! Can't wait!!
@irgendwieanders2121
June 17, 2026 at 7:45 am
I'm working on a joke based on "people don't want you to use the N-word…"
Turns by using another N-word (German origin…) as the thing your not supposed to say
@dukeallen432
June 17, 2026 at 7:45 am
Wanda: I laughhed hard at Maher joke. Felt same sentiment. Lotsa love for u.
@anthony_pickle
June 17, 2026 at 7:45 am
Is that Biggie Shortie?!🎉
@ish474
June 17, 2026 at 7:45 am
I don't expect that Wanda will see this but may e someone will show it to her. I have been rooting for you as a Comic since I first saw you all the way back when you had a husband. You truly are such a great Comic and a bridge between what comedy used to be to what it is now. So happy for all your success
@PerfectlyCandid
June 17, 2026 at 7:45 am
Great. Overdue. The reverence comes across and is appreciated. She's the best.
@BrandonCroker
June 17, 2026 at 7:45 am
Wanda is fun.
@vanessawhitneypro
June 17, 2026 at 7:45 am
Legend. 🎉
@DeezTimestamps
June 17, 2026 at 7:45 am
📖 Starting Comedy Career in DC (0:00 – 5:31)
├─ 1:37 Starting Comedy Career in DC
└─ 3:50 Early Comedy Club Experiences and Tough Rooms
📖 Finding comedic voice and bombing (5:31 – 10:49)
├─ 7:36 Coming Out and Family Privacy in Comedy
└─ 9:04 Standup bombing and parental rejection
📖 Writing for Chris Rock and Comedy Endurance (10:49 – 16:44)
├─ 12:23 Wanda Sykes Comedy Sketch Origin and Writer Qualities
└─ 14:13 Comedy Endurance and Continuous Growth
📖 Comedy Writing, Keith Robinson, and Curb Improv (16:44 – 22:42)
├─ 18:50 Casino habits and Curb Improv
└─ 20:17 Curb Your Enthusiasm Audition and Improv
📖 Audience Expectations and Political Comedy Polarization (22:42 – 28:44)
├─ 24:01 Audience Reaction to Political Comedy
├─ 25:25 Political Humor and MAGA Seriousness
└─ 27:08 Collective Responsibility and Political Corruption
📖 Passion in Acting and Career Envy (28:44 – 33:55)
├─ 30:32 Acting's Impact on Standup Physicality
└─ 32:02 Jane Fonda's Reinvention and Political Disillusionment
📖 Standup Advice, Coming Out, and Joke Development (33:55 – 40:59)
├─ 36:04 Comedy Career and Coming Out
├─ 38:03 Privilege and Childhood Gun Memory
└─ 39:33 Comedy Joke Development and Charity
@m_0863
June 17, 2026 at 7:45 am
Yes!
@commoncavecricket
June 17, 2026 at 7:45 am
Love Wanda 🤘
@WanderingFriendzone
June 17, 2026 at 7:45 am
Mike's dream guest that is also my dream guest for Mike's show ❤
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