Less than 24 hours after arriving in Baltimore, the comedy writers sitting at the Pete’s Grille counter are already looking a little worse for wear. On a bracing October morning, T.J. Shanoff, 36, an affable guy with a receding hairline and wire-rim glasses, clutched his coffee cup and tried out sleepy one-liners on the waitress. Megan Grano, 32, a lively brunette in the grips of a racking chest cold, tapped out notes on her smart phone. The pair—writers for Chicago’s famous Second City comedy institution—had already sampled Natty Boh, gotten an earful about the Colts’ betrayal, and discussed whether Baltimore resided in the North or the South. But with just four or five days to absorb all things Baltimore in preparation for writing a show about the city, they had a long way to go. Shanoff inadvertently brought that point home midway through a post-breakfast driving tour. “I noticed on one of those blue police lights it says ‘Believe,’” he observed somewhere between West Baltimore’s “highway to nowhere” and Reservoir Hill. “What’s that about?”

Grano and Shanoff’s finished product, The Second City Does Baltimore, opens Dec. 30 at Center Stage. It is a commissioned piece, one of a series the company has done in other cities, such as Atlanta, Boston, Denver, and Pittsburgh. Its reception rests on whether the writers have managed, despite their outsider status, to move beyond cliché bits about hons and crab cakes and the not-so-hilarious murder rate to something deep in the city’s psyche we haven’t fully mocked yet. Judging by reviews from other cities, the odds are fairly even.

“Beantown served canned, clichéd,” a Boston Globe headline groused about the Second City show that opened there in April. “It’s the perfect place to send tourists, out-of-town guests and anyone who thinks Bostonians are nothing but Sox-obsessed loudmouths with a mumbling mayor and an inability to use the letter R,” read a story in Metro Boston, a free daily. But the Atlanta Journal Constitution praised last year’s show there for “dar[ing] to utter what we’ve all been thinking about some of our town’s sacred institutions.” And the Pittsburgh Post-Gazette had this to say about a 2008 production: “[T]he charm and humor of these performers wards off any indictment for carpetbagging.”

Grano and Shanoff are aware that they are treading on sensitive ground. “What’s a little tricky—and we’re anticipating this in Baltimore—is that we’re gonna have reviewers come in saying, ‘Who the hell do these people think they are?’” Shanoff says. “We’re not trying to say we’re experts. But Second City has a certain pedigree, a certain way of doing things that’s very unique.”

> Email Andrea Appleton