Talk to virtually any Milwaukee comedian long enough and the name Chastity Washington will eventually come up. The proper noun will undoubtedly be sandwiched between flattering adjectives and glowing compliments regarding the hilarity she unleashes on stage, the kindness and wisdom she imparts off stage, and the inspiration she provides to the comedy community both with and without a microphone in her hand. With more than 20 years of comedy experience, television credits, a respected one woman show, as well as the love and admiration of an entire comedy scene behind her, Washington is nothing short of a local legend. Recently, that legend has grown beyond city limits, with no conceivable end in sight.

Washington first attempted stand-up at a talent show during her freshman year at UW-Parkside in the mid-1990s. “The light bulb came on,” Washington says. Though she believes comedy “found” her, she balanced her comedic calling with a teaching career. For 10 years, Washington taught middle school and high school by day while she honed her humorous hobby in comedy clubs and open mics throughout Milwaukee, along with out-of-town gigs, on nights, weekends, and over summer. Approximately a decade ago, the moonlighting comic decided she was ready to quit teaching, take the leap, and make her act her career.

“Maybe it wasn’t the right time. Who knows? I struggled at the beginning,” Washington says. “You go from being a full-time career person to being paid in chicken wings and 30 bucks. But you got to pay bills, so it puts you on a grind. You’re working, trying to get more stage time.”

If Washington was struggling at the outset of her tenure as a career comedian, it wasn’t evident to her peers or other onlookers. Comedian Liza Marie says she first saw Washington perform seven years ago at ComedySportz and she (only a few months into stand-up herself) was instantly taken aback by her.

“When I first watched her, I was like ‘This woman needs to be famous,'” Marie says. “I was dying. I was cracking up. I’d never seen anybody like her in the local scene.”

Ryan Lowe—an accomplished local comedian with a decade of experience—has seen Washington perform numerous times, including a variety of shows they’ve done together at traditional venues, open mics, and even a showcase at a suburban cigar bar. They’ll perform together again at The Underground Collaborative on Saturday. No matter the show’s location, the circumstances, or the size of the audience, Lowe says she always finds a way to win over the room.

“It’s automatic. Within the first five or 10 seconds, she instantly connects with the audience and strips away every layer that’s there,” Lowe says. “Boom, she’s got them. It’s this likeability factor that’s just unheard of.”

Combining a uniquely inviting perspective on demographic-crossing topics like family issues and gender roles with and an overriding fearlessness that, at times, finds her simultaneously dancing and wailing in grief during the same joke, Washington conveys undeniable across-the-board appeal that works equally well in what she calls mainstream and urban rooms.

“No matter what age, ethnicity or cultural background, income, if it’s funny, it’s funny,” Washington says. “I learned that from working in the deepest south side of Chicago, the deepest northwest side of this city, and the east side of this city.”

Recently, Washington has tested her act all around the country. Last year, she traveled throughout the U.S. by plane, train, and bus to perform more than 250 shows, including an extensive run of shows on the university circuit. While it takes her outside Milwaukee most of the year, she calls every night on the road “a lesson” in how her material works elsewhere.

“It doesn’t bother me. It’s peaceful. I can rest, I can pray, I can read, get centered, write,” Washington says. “It’s seeing the country and all these different people. Even though we all live in the same country, everybody’s got a rhythm in their region.”

Though she’s not around as much as she used to be, Washington’s good reputation and her standing in Milwaukee’s stand-up scene remain untarnished.

“I think a lot of people hold her on a pedestal. Not like we’re worshiping her, just as an example to what kind of outcomes can come from hard work,” Marie says. “If anything, the only [difference] that I’ve noticed is that she’s getting more recognition.”

Washington has appeared on Comic View and Coming To The Stage (both on the BET network), and HBO Def Jam. She qualified for the famed Just For Laughs festival in Montreal numerous times, and was one of 10 finalists featured in the 10th annual “Stand Up NBC” comedy diversity showcase in 2013. As impressive as those credits are, Washington says she wants to “go bigger” and continue to develop as a comedian. Additionally, she’s writing a treatment for a television show, and is trying to get her long-running one woman show “Evening Of Expression”—which she calls “a snapshot into eight different women’s lives”—closer to Broadway this year.

“That’s my baby. That’s my Star Wars, you could say,” Washington says. “It’s something that I’ve worked and milled over all these years. I really believe that it’s powerful, thought-provoking, mind-changing, and that’s why I do it. I believe in it, and I know it’s going to go far.”

After 21 years on stage, the veteran comic couldn’t accomplish much more locally than she already has. Few of her comic counterparts would refute the claim that Chastity Washington is the funniest person in Milwaukee bar none, and those who might take issue with the statement would likely only do so because details about her being supportive, gracious, humble, kind, and devoid of entitlement weren’t also mentioned.

“If you said top three Milwaukee comedians now or of all time, I’d be surprised if her name wasn’t on anyone’s list,” Lowe says. “She’s so dynamic. Very rarely have I seen her not do well, and even when she doesn’t do well, it’s still better than anyone else around here could expect to do.”

Chastity Washington will headline a showcase at The Underground Collaborative on Saturday, January 24 at 7:30 p.m. Ryan Mason, Ryan Lowe, Allison Dunne, and Jake Kornely will also perform, along with an improv set from Tall Boys. Buy tickets here.

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