Review: Chicago Comedian Drew Michael Captivates Crowd at The Den Theatre

Local comedian Drew Michael brought his stand-up tour home to Chicago last weekend. Michael performed at The Den Theatre’s Main Stage for a full audience. Maddie Wiener was the opening act.

Photo by Alex Zerman

Drew Michael has an impressive CV—last year he broke out with his critically acclaimed HBO special Drew Michael. Praise for the comic was widespread; including GQ’s assessment that Drew “represents the past and future of stand-up comedy.” The one-hour special was described by The New York Times as “thrillingly subversive,” and was the only stand-up special to receive a Writers Guild Award nomination in 2018. Michael has previously released a special on Comedy Central, two full-length live albums (Funny to Death, Lovely), and has written for Saturday Night Live.

The show started late (scheduled to begin at 7pm), but The Den’s unexpected atmospheric combination of cozy and chic distracted any antsy audience members. Seats began to fill in, and the diversion of pop music died down 20 minutes past the expected showtime. The 21-year-old opener, Maddie Wiener, has opened for a notable track record of comics and was a semi-finalist for Stand-Up NBC in 2018. Unfortunately, despite her many accolades, her performance registered as cheap. Perhaps Wiener had an off night, but her topics touched upon a taut range of subjects—from breakups and Tinder to weight gain and antidepressants. A few jokes riled up the crowd, adequately warming them up for the main act, but most seemed low-brow and simply vulgar for the sake of vulgarity.

Luckily, the opener was just an opener, and before long Drew Michael took over the mic. His performance started out slow but quickly gained momentum. Pregnant pauses were frequent, particularly toward the beginning of his set. At first, these seemed less of an artistic choice than an audience becoming public witnesses to a man’s deep inner reflection while his present surroundings fall to insignificance. Yet, as he continued, Michael touched upon this very intensity that is often noted by others, claiming it was likely something about his “deep set eyes,” or perhaps the inflexibility of his brow bones.

The comic deftly tiptoed the line between seriousness and comedy as he guided the crowd through personal endeavors. Michael posed existential questions and curiosity in a way that could only be met with silence, or laughter at the utter truth of it all. It’s common for comics to showcase a raw honesty; it is one of the best ways to break into a crowd through an unreserved vulnerability. Michael discussed therapy, intimate relationships (and the desire for sharing an intimate relationship with one’s therapist,) and the terrifying process of confronting the deep core of who you are as a human being. He described this inner exposure as “dunking your head into your own bucket of truth,” and deemed it the most terrifying act a person can attempt. Michael’s intelligence was evident and greatly appreciated throughout his set, and his honesty didn’t seem overplayed or forced. His perspective on comedy was devastating and delicate, but held up well with the audience.

The set at The Den was simple and allowed the spotlight to stay on the comedians. Located at 1333 N. Milwaukee Ave. in Wicker Park, The Den Theatre began in 2010 as one room on the second floor of a building. The Den is now home to four resident theater companies, houses seven live spaces and three bars, and boasts the most active performance and event space in the country. Check out upcoming Den Theatre shows and events.

Drew Michael’s stand-up routine was worth attending. Opener Maddie Wiener performed for 18 minutes, and Michael closed out the rest of the night, wrapping up the show at just under 90 minutes. You can purchase tickets for Michael’s shows in other cities here.

Katie Priest
Katie Priest

Katie Priest recently returned home to Chicago after receiving her BA in English from the University of Washington in Seattle. She works for an environmental nonprofit where she writes and researches grants and manages social media for expanding agroforestry in developing countries. Katie is pursuing her long-time passion for reading and writing through the exploration and review of the arts with Third Coast Review.