The Bucktown building has been standing since 1895 and, in one way or another, has always been home to a bar. In the 50s, people bought a bucket of beer and hung out all day; in the 90s, patrons would smoke inside and shoot pool in the back; and in the early 2000s, the space seemed to have a DIY feel. But in 2010, under new ownership, The Charleston transformed into what it is today: a neighborhood jaunt with great cocktails, just enough domestic and imported beers, and a rich music program.
At the front of the bar are dramatic floor-to-ceiling windows where you might find first dates or small groups of friends huddled together, drinking and talking on a weekday after work. Inside, the space is long and open with built-in bench seating lining the wall. Those who arrive early in the evening might be posted up with a laptop, but for those who arrive late and stay late, there is plenty of room to dance in the back under the disco ball.
The original tin ceiling will always be charming, but what immediately catches my eye is the fridge behind the bar. Crafted with wood with a glass window so you can see inside, the fridge at The Charleston has several doors that close with a latch system, as if they’re compartments to hide loot. Without being hokey, the whole rig looks like it was stolen from a ship and plopped into a bar in Bucktown.
The walls of The Charleston are the color of a perfectly worn-in pair of black jeans that your crush dons all year round, even in a heatwave; a little rugged yet soft. The floors are sturdy and stubborn, holding onto years of spills and stories, and hanging proudly on the back wall are two large, vintage-looking, horn-loaded speakers clad in a wood veneer that complements the rest of the space. The speakers are not shy about telling you that music is taken seriously at The Charleston.
After spending a few laidback nights at the bar, I spoke with Cassidy Slaughter Mason, who has been bartending at The Charleston on and off for almost 10 years. She’s also an actor and writer who recently starred in the play Birds of North America at Red Orchid Theatre, and is in the final phase of editing a short film she co-wrote, co-produced, and stars in called Rabbit Rabbit, streaming on Open TV in early fall.
“On the weekends, it’s kind of a destination spot for a lot of people,” Cassidy told me over the phone, noting that she works at The Charleston on Mondays, which is a dark night for theatres. “I like it when it’s chill and full of regulars.”
The space has an intimate and cinematic quality to it; it’s easy to picture you and someone else cozied up during a snowstorm or enjoying a stout while watching the rain fall. As I sat there crushless and alone one night (still very romantic, by the way), I wondered if I’d seen The Charleston in a show or movie.
“I used it for a film that I made,” Cassidy said, “and a lot of people want to use it for film or TV commercials,” Cassidy shared, telling me that a couple of beer commercials were filmed there as well. “People are really drawn to it.”
In fact, when she was in LA, Cassidy went to a bar and met the owner, who beamed upon finding out Cassidy was from Chicago. The owner told her she loves The Charleston and that she designed her bar to feel and look like Chicago. “It had a tin ceiling and everything,” Cassidy said.
On the nights she works, Cassidy curates the playlist and books the DJs, who start around 9 pm. “I started [the playlists] in 2016, and there’s a lot of different variations. A lot of the bartenders have playlists that are based on a vibe, like a rainy day one,” Cassidy said. “Mine are more temporally located.”
During a recent shift, Cassidy was playing music she listened to in 2021, which is when she was living in California and lockdown was loosening up. “No one in the bar knows that these playlists are from a really specific time in my life,” Cassidy said, “but for me, there’s something really lovely about accessing that nostalgia.” Music is a way for Cassidy to time-travel.
While some bartenders try to mold the music to fit the atmosphere, Cassidy prefers to play with juxtaposition. “My playlists are built around my taste, and not necessarily for the bar,” Cassidy said. “And I don’t take requests,” she added. Respect.
Recently, during a Saturday shift, a party bus full of women in tennis outfits pulled up to The Charleston, playing rowdy drinking games mid-bar-hopping spree.
“I was playing one of Nico’s solo albums, and it was really sonorous and heavy,” Cassidy said, describing the scene to me. “They were like, ‘Can you change the music?’ and I was like, ‘No,’” she said, making me laugh. “The clash between what was happening with them and the music I found really exciting.”
Cassidy’s playlists infuse a variety of genres, including opera, like Antonín Dvořák, Giacomo Puccini, and Georges Bizet, and country artists like Alan Jackson, The Judds, Andrew Sa, and Gram Parsons. She also tries to feature a lot of local musicians, as well, having various friends in the Chicago music scene.
“I think it’s exciting to expose people to music that they wouldn’t necessarily find [on their own],” Cassidy said. “And because of the way algorithms work, a lot of people are used to playlists or sounds that are AI-generated and a little generic.” Cassidy’s not afraid to take people outside of their sonic comfort zones.
Over the years, she’s been exposed to several local acts, and when she hears them on her playlists, it immediately transports her to the first time she saw them.
“There is a component of [remembering]. Like, ‘Oh yeah, that was the time I was at a show at Hungry Brain and first discovered Ben LaMar Gay,’” Cassidy said of the local Chicago Jazz musician. “All of a sudden, he’s proliferating every playlist from that time.”
Her playlists are also a timestamp for where she was emotionally at any given time. “With hindsight, you can listen back and be like, ‘Oh yeah, that’s when I was extremely isolated and depressed in San Francisco in 2020. Or the time I first fell in love.’ You can hear it creeping into the sound,” Cassidy said.
Cassidy also builds playlists around a character she is playing in a theatre or film role. These playlists and characters sometimes slip into rotation at The Charleston, too.
“I’m not historically building a playlist around the character,” Cassidy said, shedding light on this unique aspect of her acting process, “but it’s more so what the character sounds like to me. Thematic stuff.” The music she chooses helps fill out the world of the character, enabling Cassidy to better understand what the character is going through. Through that, she can unlock hidden motives or memories behind the performance.
After 9 pm at The Charleston, the playlist fades out and a DJ steps in. Every night, you can anticipate something new because each bartender is in charge of booking the DJ for the night they work.
Most of the DJs spin vinyl or bring in their own equipment, however, in the corner of the bar is also a reel-to-reel recorder, if anyone is an analog audio head. “The owner [of The Charleston] also owns deciBel Audio [a retail store and custom installation business in Wicker Park], so the speakers and DJ booth are really beautiful, kind of older, but highly cared for,” Cassidy said.
Over time, the number of DJs Cassidy knows has grown. She started by booking her friends, and then, through recommendations, her network built itself.
“There are a couple of DJs I will consistently bring back that I really love,” Cassidy said, naming Kaylan McQueen, Alyssa Gyorkos, Vinson Minas, Calvin Small, and Humberto Nate as a few of her go-tos. “I like to have a big variation in what they’re playing and who they are. It’s also exciting to have people who are new to DJing and give them a chance, as well as seasoned veterans,” Cassidy said. DJing has traditionally been a boys' club, and Cassidy is conscious of that, often booking femme and queer-identifying DJs.
Because Mondays are often a slower night, Cassidy can experiment more. For example, Alex Grelle is a performance artist, actor, comedian, and DJ who Cassidy keeps bringing back to The Charleston.
“Sometimes Alex will do a performance piece with [his set],” she said. “I’m not as controlling about the vibe or the music they’re going to play. It’s more fun that way.”
As Cassidy and I concluded our conversation, it was clear to me that whether you’re there alone or with a crush whose jeans match the walls, one night at The Charleston is never the same as the last.
Cassidy’s Top 5 Last Call Songs:
- Cheers Theme by Gary Portnoy
- Song to the Moon by Antonín Dvořák
- I’m So Tired by Fugazi
- Blue Monday by New Order
- Major Tom (Coming Home) by Peter Schilling