For more than 20 years, comedians of all levels of notoriety have peddled their laugh-inducing verbal wares on Riddles Comedy Clubs? stages. An airbrushed city skyline sits behind the corner stage, where such comedians as Jeff Dunham, Louie Anderson, and Drew Carey slung jokes to side-split audiences. A full bar with overhanging LCD TVs dispenses alcoholic and nonalcoholic whistle-wetters in between sets. Additionally, Riddles' lots house free parking for those driving from far-off locales or patrons who can't find a limo service that takes knock-knock jokes as payment.
Hand-cut and -rubbed with award-winning seasoning, the wings at Cigars and Stripes are smoked for more than four hours before pit masters reheat them on the grill. Then, they toss them in your choice of homemade sauces, including a buffalo-style sauce made with cayenne and a super hot sauce made with peppers and molasses. The process is emblematic of the culinary team’s barbecue mastery, which they further showcase with entrees that change throughout the week, including hand-pulled pork marinated with pineapple and mango, slow-smoked for 13 hours, and topped with chipotle corn salsa. To complement those sauce-soaked bites, bartenders keep 13 beers on tap and stock tons more by the bottle, including Delirium Tremens and Founders Breakfast Stout. Comedians grace the bar’s stage twice weekly as part of a calendar that also includes regular movie nights, TV-nights, live music, and trivia, and once a year Cigars and Stripes trades chuckles for chills with their annual Freaktober Fest, which features beer tastings, tarot card readings, and screenings of scary movies, such as Beaches.
At The ComedySportz Theatre, audience suggestions keep an all-ages, family-friendly and fast-paced vortex of scenes, games, and songs spinning in competitive shows that pit two improv teams against each other. Inside the intimate, 149-seat theater, spontaneity rules as a referee moderates the all-ages-appropriate hilarity pitched between the Chicago Bosses and The Evanston Express. At the end of each comedic duel, the points and audience votes are tallied to determine the winning team, sentencing the losers to feed the doves that live inside the winners' top hats.
The ComedySportz Training Center's seasoned instructors also teach six-week courses in the art of improvised hilarity and the essential virtues of spontaneity, risk taking, and engagement with the moment. Through scene work, ComedySportz games, and short- and long-form improv, students learn to keep audiences roaring in order to jump-start a career or become a more affable bank robber.
The quick-witted troupe of performers at pH Productions stirs up a rollicking concoction of comedy that bubbles with equal parts improv and audience interaction. Founded in 2002, the troupe's scientific moniker celebrates the onstage chemistry that leads to a great night of improv and leaves nothing but a neutral puddle of goo when incompatible performers accidentally touch. Classes teach would-be improvisers the arts of extemporaneous comedy with a focus on hands-on learning, and a slate of shows delight audiences with long- and short-form sketches, many of which have been recognized with the Chicago Reader's Critic's Choice award.
Having spawned hordes of comic luminaries in the last 30 years, including Mike Myers, Chris Farley, and Tina Fey, the revered iO Theater curates one-of-a-kind evenings of improv every night. Two spacious theaters host shows where everything from classic long-form improv and family-friendly fare to musical improv and improvised Shakespeare launch audiences into imaginative stories. A full-service bar in each theater allows audiences to hone spit-takes when sipping sudsy drafts and cocktails.
In December, The Second City—Chicago's go-to haven for improv—will open a sister theater, UP Comedy Club, whose packed calendar lists original performances by Second City comics, standup from visiting comedians, and fast-paced improv revues. In the theater’s inaugural month, visitors can indulge in giggles at the holiday season's expense during The Second City's Dysfunctional Holiday Revue, a full-length show lampooning Yuletide staples, from holiday gift exchanges to pulling clumps of white hair out of the chimney. In The Second City's History of Chicago, the troupe culls the best moments from decades of performances to create a hilarious seminar on Windy City lore. The selection of shows rotates with changing seasons and visiting performers. Every show is rated for appropriate audiences, letting parents know when to bring the kids to fine-tune their funny bones, and when to bring pet parrots to update their repertoire.