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Meet Wisconsin comedian/teacher Chastity Washington

By Peter Lindblad

Wisconsin’s own Chastity Washington didn’t have a lesson plan prepared for her entry into the world of standup comedy. 

She just got up on stage and let loose, winning over crowds with her infectious and joyful personality, as well as her funny insights on life and family in general, but specifically, the trials and tribulations of teaching America’s youth.

Going straight from the classroom to comedy clubs everywhere, the Milwaukee teacher/comedian known as the “Comedy Auntie” for local comics has been making people laugh for more than 25 years, performing at venues all over the country. 

Washington has opened for the likes of Charlie Berens, Roy Wood Jr., Tommy Davidson, Sommore and David Mann, having also headlined at Comedy on State in Madison, as well as Zanies Chicago/Rosemont and other famed clubs. An NBC Diversity Finalist and an HBO Comedy Wings winner, Washington has also appeared on BET, along with big-time events like Just for Laughs and the Martha’s Vineyard Comedy Fest.

Recently, she released her first standup special, “Live at Dandy” on Amazon Prime and Tubi. Soon, Washington will be taking over the new Laughing Tap venue in Milwaukee, at 761 N. Jefferson St., for three shows May 22-23. Find tickets, here.

Washington, who will be bringing her “Evening of Expression” one-woman show to Ferche’s Crafthouse (418 N. Mayfair Rd.) in Wauwatosa on Saturday, May 9, took time out to answer a few questions to get fans ready to see her in her element:


What was the driving force for you to get into comedy?

Washington: It really just found me. Comedy found me. My BFF signed me up to a campus talent show. It left me with knowing that this is what I’m supposed to do, and I haven’t stopped since. 

Did it go well?

CW: It did. I did well over my 7-10 minutes set time. Though it was first go-round, I was received very well and knew something had clicked. After that, had some awful sets and some great ones early. I had been encouraged since middle school to do standup but always blew it off. It wasn’t something I was in pursuit of. It found me.

How do you balance teaching and standup, and how do those two parts of your life bleed into each other? Is it just that teaching provides you with a wealth of material or is there something more?

CW: I do my best to balance the two. Keeping most, not all but most, of my travel work to the weekends around my work schedule. They bleed into each other by always having to be quick on my feet. Being able to change direction … all of those things. As far as the material, I get a lot from teaching but also get a great deal that comes from childhood, family stories and everyday life. Very early on I knew that this is what I was supposed to do.

Why do you think your comedy is so relatable?

CW: I believe it is relatable because we are all people. And even if we think we and our experiences are so different, but they are really not. We have so many more similarities than we realize. And if something is funny, it just is.

You released your first comedy special, Live at Dandy. What was the hardest part of doing that and what was the most enjoyable, and do you think that’s the highlight of your career so far?

CW: Releasing the special wasn’t so difficult with the help of Matt Kemple and Milwaukee Comedy. What was difficult was a few years before just recognizing that it was a possibility and believing I was ready for it. Recording the special is one highlight of many. What was most enjoyable was the performance itself.

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