Review: Out of The Loop Takes a Deep Dive into the Storied Stand-Up Comedy History of the Windy City

Although a little rough around the edges, the new documentary Out of the Loop is the deepest dive I’ve ever seen on the history of the Chicago stand-up comedy scene and how said scene reflects the segregated nature of the city. But the film also shows how certain groundbreaking performers dared to break through the barriers (often divided along racial lines) and get the exposure they needed to become, in some cases, something legendary. To be clear, this is not a doc about the rich Chicago improv scene (although it’s certainly addressed and quickly pushed to the side as being off-topic); Out of the Loop is about the phases and faces that make up the stand-up scene, complete with archival footage, new and vintage interviews, and a tour of a city that at one point had more than a dozen comedy clubs scattered within its borders (not to mention the thriving scene in the immediate suburbs).

Much like the city, the film is somewhat divided, as if Black and white performers are completely different entities—the only people that don’t seem to think so are the comics themselves who frequently tell stories about how funny and talented the others are. After opening with a very funny voice message from Bob Odenkirk, saying he’s opting out of appearing in the doc, Out of the Loop takes us on a tour of history to a time when no stand-up clubs existed, so performers had to beg to step in between performing bands and in blues bars or anywhere that featured a stage and something resembling an audience.

Elder statesmen like Tom Dreesen and Jimmy Pardo give their accounts of the rise of the comedy scene in Chicago, but when the 1980s rolled around, things begin to pick up, and we get stories from the late Judy Tenuta, Jeff Garlin, Marsha Warfield, and others about what it was like finding a place to perform, even when operations like Zanies were thriving. 

With interviews directed by Michael Alexander and editor/producer Scott Perlman putting together a solid timeline for this rise and fall and rise and fall journey, the film illustrates how the Black clubs on the South side were the leading places to see some of the funniest performers the city had to offer, like Lil Rel Howery, Hannibal Burris, Deon Cole, Orlando Reyes, and the original king of comedy Bernie Mac, whose presence practically takes over the film at a certain point. If you were lucky enough to see the great documentary Phunny Business: A Black Comedy, about the high-end South side comedy club All Jokes Aside, operated by Raymond Lambert (who is interviewed for this film as well), then you know some of the best stories from this period and what it took to succeed and thrive.

Perhaps Out of the Loop’s VIP, however, is Dwayne Kennedy (also given a producing credit on the film), whose influence and storied career all stem from his desire to appeal to all audiences without feeling like he had to choose. This process didn’t always work out in his favor, but he’s clearly a favorite among the locals, and he has some of the best stories and finest insights of anyone in the movie. Rounding out the interviews are the likes of Chris Redd, Megan Gailey, Patty Vasquez, Kyle Kinanae and Lance Crouther (Pootie Tang), as well as Pete Holmes and T.J. Miller (who actually got his start being one of, I’m guessing, very few white comics who came up on the South side, almost by accident). The two of them are interviewed together for reasons I’m not sure I get, since their stories are vastly different, but also quite unique from some of the other comics.

What comes to the surface after listening to all of these comedians talk is that you have to be willing to endure the worst the world has to offer, in terms of human beings and accommodations, in order to make a living making people laugh. And if you can do that, then you also have to be funny. It’s a frequently thankless, competitive, brutal occupation, but when a performer clicks with an audience, it’s also addictive. And Out of the Loop captures the entirety of that experience quite beautifully.

The film is now available on all digital platforms.

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Steve Prokopy

Steve Prokopy is chief film critic for the Chicago-based arts outlet Third Coast Review. For nearly 20 years, he was the Chicago editor for Ain’t It Cool News, where he contributed film reviews and filmmaker/actor interviews under the name “Capone.” Currently, he’s a frequent contributor at /Film (SlashFilm.com) and Backstory Magazine. He is also the public relations director for Chicago's independently owned Music Box Theatre, and holds the position of Vice President for the Chicago Film Critics Association. In addition, he is a programmer for the Chicago Critics Film Festival, which has been one of the city's most anticipated festivals since 2013.