Comedian Ashley Ray Shoots From the Hip

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Los Angeles-based comedian and writer Ashley Ray has loved being on stage ever since she started performing slam poetry as a middle schooler in Rockford, Ill. Her mom would bring her to open mics and Ray honed her skills attending poetry classes at her local community college.

“Growing up in Black churches and Black family and talent shows, I was always the kid where they’d be like, ‘Ashley, memorize that Maya Angelou poem and say it for everybody,’ and I always loved it. I would recite Phenomenal Woman for my grandma and now that I look back, I’m like, oh, I liked speaking. I just liked talking and getting attention,” Ray tells me over Zoom.

Eventually, she moved away from spoken word—which she competed in and performed through college—to storytelling when she relocated to Chicago. But that also didn’t quite fit for Ray; she was made for comedy, which is evident when you listen to her hilarious debut album Ice Cream Money, released via Blonde Medicine on March 1.

“Slowly I realized I didn’t like the expectations that are placed on Black women when you do storytelling and spoken word, which is that you’re there to be like a wise sage mystic for a bunch of white people who want to be enlightened,” she explains. It became evident that comedy was her calling: “I liked the funny parts, I liked the parts when people would just laugh and we moved on… That’s when I was like, ‘Oh, that’s stand-up.’”

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Ray started doing comedy in 2016, but she’d long had a love of “comics’ comics, the road dogs,” like Maria Bamford, Greg Giraldo, and Mitch Hedberg. She admired their dedication to the craft and applied that same persistence—constantly doing shows, constantly improving her material—as she was coming up. Her home base of Chicago was an ideal place to cut her teeth as a comic, since there wasn’t too much industry pressure and the location made it easy for her to tour. She flourished in the same scene that produced idiosyncratic talents like Sarah Sherman and Meg Stalter. Soon, though, Ray started a job that would fly her between the Windy City and New York. When work was done, she did stand-up at as many venues as possible, and as a tribute to the “first place where I felt like I was a real comedian,” she taped Ice Cream Money at Brooklyn’s Union Hall.

Like any up-and-coming comedian in the 2010s, Ray joined Twitter (I refuse to call it X). If you’re even remotely active on the social media platform, you’ve probably come across her hilarious profile, on which Ray shares her various opinions about life in general, but primarily about TV and pop culture. Ray found fame on the site with her barbed and uproarious tweets, and thanks to her unexpected social media celebrity she’s had people like Seth Rogen, Roxane Gay, and Nicole Byer on her podcast TV, I Say. She’s grateful for Twitter in terms of it opening up opportunities for her, but confesses that “I’m not curating anything… I’m just shooting from the hip.”

“The stuff on Twitter is the bottom of the barrel trash. The good stuff is elsewhere,” Ray tells me with a laugh. After all, consider her writing, podcasting, and stand-up prowess; Ray was dubbed an HBO Max Queer Comic to Watch in 2021 and a BET Black Woman Comic to Watch just last year. She wrote on Alabama Jackson (Donald Faison’s Adult Swim comedy) and hosts a monthly live showcase with fellow comedian Barbara Gray (of Lady to Lady and Free Britney fam).

And when it comes to Ray’s album Ice Cream Money, it is an utter joy to spend time with. Her jokes are sharp and delivered with shrugging confidence. She riffs about Pete Davidson’s appeal, dating a flat earther, and telling her mom she’s bisexual and polyamorous (the track is cheekily titled “It Takes 21 Minutes for Ashley to Mention She’s Polyamorous”). When I ask Ray if there was a particular moment she realized she was poly, she tells me that growing up with a single mom who ran a daycare, she “didn’t have a traditional idea of relationships or how love happens.”

“There were so many kids that were with my mom from when they were born, basically, who saw her as a second mother and loved her, and I shared my mom with all these kids, and it never made me angry or upset. I was always just like, ‘Yeah, she is really awesome, isn’t she?’… That kind of impacted how I wanted to love in the world, and I didn’t see it as a thing that had to be limited,” Ray says.

From jokes about polyamory to family secrets, Ice Cream Money solidifies Ray as an exciting comedic voice. She’s under no illusions about the state of comedy at the moment, noting that no one exactly “makes it” anymore, but she aims for success as seen in the careers of the Maria Bamfords and Laurie Kilmartins of the world: not too likely to get stopped at the grocery store, but continually working and revered in their field. With her talent and dedication to performing, it feels like just a matter of time until Ray reaches that level.

Ice Cream Money is out now wherever you listen to comedy.

Clare Martin is a cemetery enthusiast and Paste’s assistant comedy editor. Go harass her on Twitter @theclaremartin.