Credit: Michael Brosilow

For years, a Chicago illustrator named Bill Utterback created ink drawings to commemorate Second City revues, catching company members in caricature as they did some signature piece of business. If you’ve been to Second City you’ve seen those drawings on the lobby walls—silly yet iconic images ranging back to the mid-1970s. Utterback died last year, so there won’t be any more Utterback art. But a couple times during the new Second City E.T.C. show, Sky’s the Limit (Weather Permitting), I felt a little like I was channeling him. Like I could see how he would’ve handled certain moments, gestures, faces. Some bits just looked to me as if they were already up there on the lobby wall.

Does that mean they’re instant classics? Or that they’re so exaggerated that they simply come across as cartoons? Well, yes. Both.

At least one sketch in Sky’s the Limit is an honest-to-god candidate for the greatest-hits collection. That’s the one in which Tim Baltz plays a guy with social anxiety disorder, trying to make it through a first date by referring to a pile of three-by-five cards on which he’s written conversation points. (“You don’t say! Please elaborate.”) Though he’s lucky enough to get inadvertent help from his waiter—Michael Lehrer, directing such ridiculously crass pick up lines at the date that a leg-humping pug would seem suave by comparison—the SAD guy’s inhibition is so extreme that you just have to accept the notion that he’s willing to try anyway, and that his date, played by Mary Sohn, is willing to sit there patiently while he does so. But in the end, it’s exactly that implausible willingness that makes the sketch so charming. Delicately wrought on both sides, Sohn and Baltz’s pas de deux is a celebration of tenacity in the face of loneliness—very much in the best traditions of Second City’s bittersweet relationship narratives.

Way over on the other end, with the cartoons, sits a piece featuring Baltz and Brendan Jennings as neighborhood CAPS volunteers who get a little overzealous as they investigate a crime. Shots are fired. But, more important, funny walks are walked and electric-tape mustaches are worn. The sketch is completely incomprehensible, loud, silly fun. Jennings, who occupies the Chris Farley spot in the ensemble, has a canny way of using his odd looks so that he can come off simultaneously unhinged and teddy-bear huggable. He’d have made a great subject for Utterback.

As would Sohn. Her restraint in the social-anxiety-disorder scene notwithstanding, Sohn mostly plays things very, very big—and for some reason, despite the fact that she appears to be of Asian heritage—black. As a mother in a sketch about sons acting out their bad-boy fantasies, and again during a song in which the female cast members rail against the conservative “war on our pussies,” Sohn seems to be going for an updated version of Flip Wilson’s Geraldine. Not that I mind. I mean, she’s very good at it. It’s just a little puzzling.

Lehrer, by contrast (and maybe by design, when you consider how many outsize personalities there are in this cast of six) is usually deadpan subtle. During a sketch opposite Jessica Joy—another relationship scene, in which he’s a 35-year-old, substance-abusing, but self-aware washout (“I’m not better than this.”) and she’s his hapless, endlessly hopeful girlfriend—Lehrer acts the character and lets the jokes take care of themselves, to strong effect. Even his version of outlandish has an interiority about it. He doesn’t give up anything easily.

If you can stand that much hilarity, you might want to see both Sky’s the Limit and the current main-stage show, South Side of Heaven. They make an interesting pair. Both are basically concerned with how fucked we are, on a micro as well as macro level. But South Side of Heaven is a lot more pessimistic—even, at times, savage—about it. Sky’s the Limit, meanwhile, is like the girlfriend Joy plays: always ready to believe. And, now that I think of it, like the SAD guy Baltz plays: blessed with an implausible willingness.