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
Seven strapping men in swashbuckler shirts improvise a two-act Shakespearean play based on a title suggested by the audience. At the show I saw, "The Taming of the Jew" inspired the Bard's usual themes (religion, family, betrayal) and plot devices (murders, disguises, fortunes gained/lost) as well as an uncomfortably funny circumcision. Director-performer Blaine Swen, a veteran of long-form Shakespearean improv who swears they don't conspire during the intermission, has assembled a vigorous ensemble of actors and proven improvisers. Their experience doing Shakespeare flowers in the language: they relish iambic dialogue, execute perfectly timed asides, occasionally utter rhyming couplets (some hilariously forced: "Let us be quick-sa, and get to the bar mitzvah!"), and drop parodic phrases ("scurvenous knave," "midfortnight report") and well-placed anachronisms (the bar mitzvah had a DJ). Even the ending echoed the real plays: story lines resolved tidily--and uproariously. (RH)
$14
If pimpin' ain't easy, pimprovising must be even harder. But the five members of Pimprov project a scary ease as they dress and cavort like "Super Freak"-era Rick James (only with more accessories) and smoothly assimilate audience suggestions into thug-themed short-form games. The group stays heavily engaged with the crowd throughout this high-energy show, bringing people on stage and carrying on multiple side conversations during and between bits. What I enjoyed most were their hilarious, spontaneous dancing (from tap to b-boying) and varied characters. These are no one-trick pimps: at the show I saw they shrewdly played everything from north side trixies to blue-collar Chicagoans. --Ryan Hubbard
$12, BYOB
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
The current incarnation of director Jason R. Chin's production is smart. On the night I attended this show, based on audience contributions of news stories, a sketch involving Bipedal Locomotion Enterprises would have taken a prize for vocabulary alone. The ten-member ensemble also made casual references to Ernest Hemingway, Norman Mailer, and William Golding. And how many twentysomethings can do an accurate Alfred Hitchcock impression extempore? Instead of going for the broad and vulgar, these folks more often opt for the microcosmic. A patriarchal defense of polygamy is transformed into a wife lamenting the responsibilities of having multiple husbands. A report about terrorists plotting via Internet cafes sparks visions of subversive activities impeded by spam, pop-ups, and IMing. The players exhibit a genuine rapport: articulate dialogue unfolds logically, swiftly, and concisely. --Mary Shen Barnidge $14
Every Saturday at midnight, The Hot Karl folks start their gig by announcing that they're going to create the foulest, most disgusting fully improvised show in Chicago. Then they do it. The group's name comes from a sex act that involves pooping on your partner, and when I recently saw the show, the MC set the tone by asking for audience suggestions while riffing on the subject of fisting. The long-form improv that followed involved anal and oral sex, breast grabbing, and lots of dick jokes (hardly surprising since six of the eight performers were men). The material was very funny and very blue--much bluer than when I last caught The Hot Karl in 2002. The odd thing is that the grosser the players got, the more expertly they improvised: they were all in tune with one another, they never stumbled, and they treated the other performers' ideas with a respect only the best, most trusting troupes manage. Even an obvious accident, when one person initiated a montage sequence just when the scene was taking off in a different direction, was called back several times. Just as impressive are the rich, uncliched characters, deftly created almost as asides as the performers make their way to the next smirking reference to a muff or johnson. --Jack Helbig
$10
Starting today, Eno Wine Room in the Fairmont hotel will offer blind tastings every Sunday evening; people who can correctly identify five attributes (like age, region, country, and grape) of three wines get their flight for free. There are two levels of difficulty, one aimed at the average wine drinker and the other created for aficionados. —Julia Thiel $25-$30 per wine flight
A comedy supergroup consisting mainly of former members of People of Earth, 3033 creates some of the liveliest, most consistently solid improv around. Members Andy St. Clair and Alex Fendrich have been highlights of recent Second City E.T.C. shows; Rush Howell, a lawyer by day, is one of the scene's wittiest performers; and Bill Arnett and Danny Mora are personable comedians with off-beat senses of humor. Unlike most troupes at iO, 3033 doesn't stick with the Harold improv format. Instead, they play it loose, letting an audience suggestion and Jason Chin's playful music and light effects steer them. At a recent show the topic of gangs inspired a hilarious 70s-era game show. --Ryan Hubbard
$5