Six years ago, Whitney Chitwood was living in New York, trying to make it in theater, and feeling disillusioned, "because I did it all my life. So I would go to comedy clubs and watch shows a lot, and got bit by [the comedy bug] that way. I just wrote on my own and didn't perform for anyone for maybe six months. And then I got very drunk and went to my first open mike. When you do it once, you get sucked in, for sure."
Chitwood has just released her first full-length comedy album, The Bakery Case—named after the Masterpiece Cakeshop Supreme Court ruling. On the album—released Oct. 18 through Stand Up! Records and recorded at Chicago's Green Mill, where Chitwood has been a frequent performer with the live magazine show The Paper Machete—she, indeed, talks about Masterpiece. Ironically, Chitwood noted that she performed several times in Fort Collins, Colorado, while shaping the material for The Bakery Case. ( The bakery is located in Lakewood, Colorado. ) "They were the first place to have me headline a festival," she said.
But Chitwood's comedy isn't solely directed through a political lens. In the segment entitled "A Bigot, A Baker, A Wedding Cake Maker," Chitwood ties Masterpiece in with her own experience confronting the infidelity of a longtime partner. When a friend tried to console her by saying "Don't hate the player, hate the game," Chitwood responded, "It's CHEATING. If [NBA player] Steph Curry ran around during the playoffs hitting people in the head with hammers, you wouldn't say 'I hate basketball!'"
Chitwood tried Los Angeles for a while after deciding to pursue stand-up, but she said Chicago gave her the environment she needed to hone her voice and her chops. "I am forever and eternally grateful to the Chicago comedy scene," she told Windy City Times. "I think it's the best in the country, just in terms of diversity and creativity. Chicago is in an interesting position specifically as a comedy city, because ... you come here, you gestate and then you shoot out to a coast. It's a breeding ground. There are a lot of people in the community who want it to be recognized as more than that. It's not just the place to come and learn how to ice skate and then go play hockey somewhere else."
Simply taking the stage as a queer woman constitutes a political act, Chitwood noted. But she also said, "I feel like everyone in Chicago is kind of queer. It's like a really super-queer city. It feels like a place that is nonjudgmental in terms of identity, so I can be 'Yeah, I'm a dyke—now, can we move on?'"
Chitwood said that she's moved on a bit from the material in The Bakery Case. She has developed about a half-hour's worth of new material for her second album, and she noted that it's moving in the direction of even longer-form material, stating, "There are maybe four stories, at the most. It's sort of long-winded, I jump around a lot, and I want to give people a chance to catch up."
In the live performance recorded for The Bakery Case, it's notable that Chitwood isn't afraid of taking longer pauses to let an image or a line land with her audience, rather than hurrying them along to the next point or set-up. Although she also pointed out that she's done more surrealist bits in the past—like opening her set by speaking fake French for a few minutes—the challenge and the joy for Chitwood lies in figuring out how the stories connect.
The material she's working on now comes out of a couple of different experiences, including the death of her grandfather earlier this year. "A lot of it is centered around like growing up on the farm and all of the various disasters that happened there," Chitwood said. ( Growing up in a small town outside Peoria, Chitwood also became a self-described "horse girl," which has led to a series of horse-themed memes fans have shared on her Instagram. )
But Chitwood said she's also interested in exploring how "we as a society don't do things just to feed our soul anymore." She pointed to the influence of social media as one of the factors; in fact, a longer essay on that subject that Chitwood performed at the Green Mill for the Paper Machete caught the attention of fellow comedian Maria Bamford and helped turn Bamford into a fan.
Being on the road three or four months out of the year can be a strain, but Chitwood has found returning home to Chicago's comedy scene helps feed her own soul. "In New York, it's like clubs and bar shows and here it feels like there's just a whole slew of odd shows that are in weird places with really cool audiences," she said.
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