At the Briar Street Theatre since 1997, the cobalt zanies have added wizard-worthy tricks to an already potent mix of visual puns, physical stunts, and cultural commentary. The latest edition conjures up a 2.5-D universe, giant "GiPads" that perform outsized multitasking, and Lady Gaga hat spin-offs. The same subversive spirit fuels the show's still-potent signature bits, including splatter-crazed "paint drumming." The secret of their cerulean success? Understanding that laughter and thought can be BFFs. —Lawrence Bommer $49-$59
A holiday hangout in your grandparents' basement in the wee hours, with inebriated uncles and cousins telling tales of woe and failure (they were drunk then too)—it's a little like that. Comedian Sean Flannery's The Blackout Diaries returned to the 70s-style Lincoln Lodge this past January, having begun there with a short run two years ago before moving to a monthly gig at the Beat Kitchen. It's weekly now, with a Malort sponsorship to boot (and a podcast launching May 1). No qualms about it, the show is about drinking (and occasionally smoking) yourself into enough of a stupor that a great yarn comes from it—and hopefully some shocking photo and/or video documentation, as well. It finds humor in the bleakness of the bender. Each week's stories come from a mix of comics—I was fortunate to catch both Chris Condren and Brian Babylon during a recent visit—and everyday Chicagoans, many of whom Flannery probably met while hugging a mug of Old Style at a bar, and many of whom probably have stories to outshine the pros. Example: The amiable postal worker and former speakeasy owner, known simply as "Floyd," who once had a time in Malta that consisted of the attempted liberation of a sex slave and the maniacal bare-fisted bashing in of a small automobile. And that's just the CliffsNotes version. Flannery is a sharp, expert host—benefiting, no doubt, from the show's increased frequency—who keeps the flow of guests steady without appearing hurried. He supplements the Q&A portion with clever inquiries if the audience isn't speaking up. Regardless of the heavy content—drinking until you climb on top of something and then fall off that something isn't actually always a blast—the mood is unceasingly light, and you're probably drinking anyway. So go make a memory. —Kevin Warwick
For someone mourning the lack of live studio audiences in Chicago since Oprah's departure, this late-night talk show provided welcome relief. And drinks, not Kleenex, were free flowing. On the night I attended, host Tom Bambara interviewed members (human and canine) of the Dog Saving Network and graphic designer Kevin Scarbrough. The dogs' cuteness factor was high, but Bambara's distaste for slobber and witty banter were equally amusing. Then he introduced "more tame but equally as hairy" Scarbrough, who reminisced about drunken tattoos and crazy clients like Big Ass Dog pet food. Andi Woody was charming as Bambara's less-flustered cohost, and musical accompanist James Manno coolly played the sunglasses-wearing Paul Shaffer to Bambara's Letterman. —Marissa Oberlander
I'm pretty sure I fall outside the Cupid Players' target demographic. Judging by this show's content, the troupe's ideal audience member is young enough to be weirded out by the thought of his parents having sex but old enough to worry that he's starting to act like his dad. He dreads romantic rejection almost as much as he fears commitment. And he's not above a hand of strip solitaire. A longtime married man with kids, I don't merely fail to fit the profile--I may be its antithesis. But I had a great time with Cupid Has a Heart On all the same. Directed by Brian Posen, who also plays piano and sings barbershop bass, this late-night show takes a standard element of improv revues--the satirical song--and makes it a raison d'etre. A charmingly goofy cast of ten performs no less than 15 original ditties, mostly keyed to the sensibility of the young, single, heterosexual urban male on the make. That this doesn't result in an unwatchable testosterone fest is testament to a wit that's always firmly based in character and in situations that remain truthful however far they get pushed. Also see this Reader's Choice review and video clip from the 2008 Best Of Chicago issue. --Tony Adler $20
Baby Wants Candy--a tight troupe now famous for its improvised musicals--began in 1997 as one of the dozens of ImprovOlympic teams formed every year. Somehow they've avoided the usual dissolution of such groups. More impressive, they've never experienced the artistic conservatism that paralyzes improvisers eager to "do it right"--and reap the reward, presumably, of a career in NYC or LA. Instead the troupe has become the very model of smart, physical, quick-thinking, and just plain silly long-form improvisers; they still play well together and manage to entertain. Inspired by the improbable suggestion "So this is it" at the show I saw, nine actors (backed by the five-member Yes Band) improvised a complicated, hilarious, tongue-in-cheek tale of three partnerships on the rocks--two marriages and a professional relationship--and the narrator who helps bring the couples back together. --Jack Helbig $15
At the start of each show an all-star ensemble creates a tableau onstage, then asks after a blackout, "Where in Chicago did that take place?" "Soccer practice" was the response the night I was there, and after an hour the improvisers--intensely alert and feisty--had crafted a veritable community, complete with idiosyncratic characters, unpredictable backstory, and tragicomic intrigue. Veteran T.J. Jagodowski, recognizable from a series of Sonic commercials he's done with quick-witted cast member Peter Grosz, played a thick-accented German coach. Abruptly launching a new scene by charging to the front of the stage, he squatted and gestured as he yelled at his coed youth team, "I will yank on your nuts like the Hunchback of Notre Dame working a bell!" --Ryan Hubbard $8
Susan Messing's weekly show, where she pairs off with a guest "friend" for an hour of purely improvised comedy, is one of the funniest entertainments in town. Messing is deeply talented: her acting is focused and nuanced, and she's got one of the the sharpest shit-detectors around, allowing her to cut or extend scenes like a good director. She works with a different "friend" at nearly every performance, often for the first time ever, and each prods her in unpredictable ways. But Messing stays on her toes, finding newer and quirkier characters—like a chatty old lady who sings musical numbers and pop songs at work or a wife from a 1940s screwball comedy who encourages her husband to tie her up—and the proportion of what works to what doesn't is a testament to her congeniality, experience, and broad intelligence. Messing was my pick for Best Improviser in the Reader's 2008 Best Of Chicago issue. --Ryan Hubbard
$5
Music, poetry, comedy, monologues, and more are welcome. $10
Five-minute performances by stand-up and sketch comics. $5
Hosted by Bretty Lyons and Nathan Jansen, audience members are invited to perform improv with some of iO's "best veterans."