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Comedian keeps the crowd rolling in laughter and in other ways

Comedian Ashley Ray
Sela Shiloni
Comedian Ashley Ray

A Rockford native is making a name for herself in the entertainment world. She was recently a guest on National Public Radio’s Wait Wait… Don’t Tell Me and HBO Max comedy special Human by Orientation.

Among other things, Ashley Ray is a comedian, tv critic, writer, and podcast host. She proclaims herself to be “the most famous bisexual solo polyamorous Black queer comedian. “

“So, I like to just put it out there like I'm queer, I'm bisexual, I am polyamorous,” she said. “These are things I'm going to talk about in my jokes, you know, so be comfortable about it. It's not something I hide. It's not something I'm going to be ashamed of.”

Ray was born in Texas but grew up in Rockford. She said her Rockford upbringing helped plant the seed for her career.

“When I was a kid,” she said, “it was around the time that like Ellis Arts Academy opened and they had like a summer program where I would go, and I could take like dance classes and acting classes.”

Ray started watching comedy in high school and realized that comedians were “truth-tellers.”

“You watch George Carlin for the first time and you're like, ‘Whoa, I didn't know that you could say these things,’” she explained. “And that's what really got me kind of started. And I started going to theater camp at NIU and DeKalb.”

This was the start of her desire to be a funny person, but Ray said her mother wanted her to be practical. Ray said she didn’t think being a comedian would be a feasible career path, so she focused on something else she loved to do -- writing.

She wrote for the Rockford Register Star in high school and attended a journalism camp at Eastern Illinois University. She went to college in Massachusetts and that’s where she sharpened her writing skills. She took screenwriting courses and started writing essays about the history of 80s Black television shows.

At that point she figured out she could write criticism for television programs. She came back to Illinois but decided to live in Chicago. She started working at The Onion and said she realized then that she could do comedy. Her first show was in Chicago. That night Sarah Sherman, also known as Sarah Squirm, and comedian Rebecca O’Neal convinced her to take the stage.

“They knew me from doing storytelling stuff. I also used to do like the Moth and slam poetry and stuff like that,” Ray added. "And they were like, ‘you know, you should stop being so serious and just focus on the funny parts and do an open mic.’”

These days, Ray is juggling many facets of her career at the same time. She now has a podcast called “TV, I Say with Ashley Ray.”

She’s continuing her work as a freelance tv critic and pop-culture journalist. She also works in advertising and – of course -- does comedy. Ray said she has yet another skill in her toolbelt.

“I am known as a weed influencer, which is, you know, something that I wanted to achieve my whole life,” she said. “And to every teacher who may be listening in the northern Illinois area who told me I would never become anything if I smoked pot, you were wrong. OK, you were so wrong. Everything I am today is because I made the choice to start smoking pot.”

In 2019, Ray moved to Los Angeles. She said this was finally an opportunity for her to be loud about the fact that weed is a part of her creative process.

“But I think a big part to me of getting people to learn about weed,” she said, “and to understand it as not just this drug, but as like a helpful plant that can be used as medicine is to kind of break down the barriers of like, what people think weed is.”

Although Ray lives in Los Angeles, she said northern Illinois is where her heart is.

“The cornfields of DeKalb, Illinois are some of the is like — one of the most beautiful places in the world to me. I love the Midwest and northern Illinois,” she said. “I'm like a – someone, one of my friends, said that I'm like a true daughter of northern Illinois.”

And this northern Illinois offspring is successfully spreading her talents across the country. Her podcast was picked up by Ear Wolf Network and the second season will start in July. It can also be heard on other podcast outlets.

As for the rest -- she’ll keep juggling.

  • Yvonne Boose is a current corps member for Report for America, an initiative of the GroundTruth Project. It's a national service program that places talented journalists in local newsrooms like WNIJ. You can learn more about Report for America at wnij.org.
Yvonne covers artistic, cultural, and spiritual expressions in the COVID-19 era. This could include how members of community cultural groups are finding creative and innovative ways to enrich their personal lives through these expressions individually and within the context of their larger communities. Boose is a recent graduate of the Illinois Media School and returns to journalism after a career in the corporate world.