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Get Your Laugh On at Chicago’s Best Comedy Spots

May 16, 2018 by Dan Jakes
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“Wig Bullies” at Chicago Nerd Comedy Festival.

Chicago’s network of comedians is often described as one big — sometimes dysfunctional — extended family, and whether you’re looking for an improv show or a headlining standup, you’ll find some of the best comedians in the Windy City. Check out the hilarious offerings around the city.

The Annoyance Theater
Smack-dab in the middle of Lakeview’s sprawling nightlife scene, The Annoyance Theater’s bar features a few details you’re unlikely to see at other comedy venues: (a) a profanity-laced chalk sign that proudly declares “We Have No Drink Specials!” and (b) patrons hanging out and drinking affordably priced beer regardless of whether or not they’re seeing a show that night. Even after moving in 2013 from its storefront Uptown roots to its more refined Belmont Avenue digs, the rebellious, vulgar, big-hearted, absurdist spirit that’s been driving artistic director and founder Mick Napier’s company since the ’80s is alive and thriving in a new generation of Annoyance comics. Seven nights a week, solo artists and troupes perform some of the best and and most subversive long-form improv, stand-up, open mic sets, and original highbrow-lowbrow musicals you’ll see anywhere in the city. Current highlights include the long-running “Steamworks: The Musical” and “Striking Out.”

Charna Halpern and the late Del Close are to improv comedy as what RuPaul is to drag— they may not have invented the art form, but their theories about it and contribution to it left and continue to leave an indelible influence on the modern understanding of it. Today, the company Close and Halpern founded in 1981 continues to be a preeminent educational institution for comedians who are serious about taking their craft to the next level. As the self-dubbed “Mecca of improvisation” and inventor of The Harold, iO features nightly long-form teams, sketch comedy, solo showcases, and its own experimental blend of The Moth-style storytelling and karaoke. This spacious, double-decker, multi-venue complex in River North is a playground and launchpad for up-and-coming artists where audience can expect to find a little bit of everything. First time visitor? Check out the “uproariously” funny “Improvised Shakespeare Company.”

Second City
You don’t have to be a Chicago native to have heard of the famous Second City or its seriously deep bench of hilarious alumni, but the reputable theater is hardly just for tourists. Out-of-towners and locals alike enjoy some of the city’s current top comedic stars in Lincoln Park’s prestigious, renowned comedy and education institution, which is currently showcasing its 106th sketch and short-form improv revue. The Second City is arguably the most polished comedy club in Chicago, where onstage risks are backed by seasoned talent and dynamic, well-synced troupes. The mainstage revue sold out? No fear— Second City’s E.T.C. Theater, Up Comedy Club, and intimate Studio theaters feature creative, intimate, experimental (often shorter) shows. For fans of musical theater, the improvised “Baby Wants Candy” is a must-see.

The Blackout Diaries
Chicago is a storyteller’s kind of city. From the Paper Machete “live magazine” at The Green Mill to the LGBTQ-focused “Outspoken!” at Sidetrack to the immensely popular (and recently concluded) “Salonathon” at Beauty Bar, there’s no shortage of authors, poets, journalists, comedians, and amateurs with stories to tell and audiences ready to engage with them live. Sean Flannery’s long-running comedy series, which he curates and hosts, taps into another formidable Windy City pastime: boozin’. Every Saturday at 10PM, a roster of comics and civilians share their best tales of drunken debauchery, be them cringe-inducing or triumphant, then interact with audiences for a Q&A. And Flannery has the cred to back up his alcohol-induced claims to fame: Not only has he earned the dubious title of “Best Drunk” by the Chicago Reader, but his show is sponsored by that most Chicago of Chicago liquors: Jeppson’s Malört.             

Improv comedy is not a competition— usually. The folks at ComedySportz, though, buck that trend head on in a red team versus blue team showdown of short-form comedic wit during its 90-minute namesake show. An emphasis on family-friendly, age-appropriate jokes and an embrace of the lighthearted, low-stakes gamesmanship popularized by television shows like “@midnight” set this club apart from traditional Harold teams in the city. Located in the heart of Chicago’s Lakeview neighborhood, ComedySportz sticks to the fundamentals and rarely strays outside its lane— the title show and a Sunday night house team set currently dominate its entire calendar.