The Laugh Factory, 3175 N. Broadway in Chicago.

The Laugh Factory, 3175 N. Broadway in Chicago. (Chris Sweda / Chicago Tribune / May 5, 2012)

In a new feature on The Theater Loop’s Funny page, freelance writer Jason Heidemann trolls Chicago’s stand-up clubs, wandering all over the city and suburbs. In this space, he’ll report back his musings on the jokes, the talent and the moods of the rooms.

- Chris Jones

Beginnings are tough. The comic who steps into the spotlight has maybe 30 seconds in which to capture the attention of a room full of bachelorettes, drunks and awkward first dates before their minds begin drifting irresistibly toward their cell phones.

I’m thinking about this when I run into standup Danny Kallas at  Comedians You Should Know, a weekly showcase he co-produces every Wednesday at Timothy O’Toole’s. He’s not on the lineup tonight, but I see him again on Saturday at the Laugh Factory where he is hosting Chicago’s Best Standup and later ask him how he kicks off a show. “In those first few minutes, getting their attention is much more important than getting them to laugh,” says Kallas. “People got a lot on their minds. They’re thinking about how much they hate their boss, spouse, etc.”

But even if the host is a hit, each subsequent comic to hit the stage has to win the crowd anew. Jeff Steinbrunner, the next guy up, tells me the key lies in taking the temperature of the room. “I'll riff off the host's material, point out things about the room, begin crowd working immediately or, more often than not, simply start with my strongest scripted joke,” he says. Tonight, Steinbrunner goes straight for goofy: “I’m here to tell you jokes. If that doesn’t work we’ll move on to tickling,” he says lurching toward an unsuspecting guy in the front row. Later in his set, he kills it with the best one liner I hear all week: “I believe in karma. Every time I cheated on my last girlfriend I would think, what did she do to deserve this?”

The headliner at the Laugh Factory show is comedian Megan Gailey. Cut from the same cloth as booze hounds like Chelsea Handler and Amy Schumer, Gailey has been nailing it this past year. But even she doesn’t take a single second of her set for granted. “The first few moments on stage are so crucial; they have to like you,” she says. “I think a lot of times crowds see women and immediately think we won't be funny.” Sex is an immediate attention grabber and Gailey knows it. She opens with a joke about using a friend’s Facebook picture to pleasure herself and the awkwardness that ensues when she runs into the person later that day. It receives a medium laugh, but more importantly the crowd is into her. Gailey is safe tonight.

Some rooms, meanwhile, are just plain tough. It is cold and brittle outside when I duck into the cellar at the Crocodile Lounge to check out StandUp, StandUp, a Thursday showcase. There are maybe half a dozen other people in the joint when I take a seat close to the hour; the DJ is spinning "Chicago, Damn" by Bobbi Humphrey.

Though the room eventually fills, the crowd is ornery. The seats next to me keep turning over and the current inhabitants won’t shut up. Host Ken Witzgall kicks off the show with a timely joke about the reopening of government after a two-week shutdown. “It’s nice to know the government is as financially stable as I am,” he says. It lands alright.

Tommy Mac, meanwhile, opens with a bit about his awkward fashion sense and later finds his footing with few savory one-liners including, “It’s nice when a girl calls you babe, but it sucks when she calls you Babe 2: Pig in the City” and, “Type II diabetes is kind of fun because it’s DIY,” but it’s comedian Kevin White whose set intrigues me. White, a charismatic guy with heaps of energy and an irresistible set of pearly whites tends to bend at ninety-degrees when he’s being emphatic, like a physical expression of an exclamation point. When he hits the stage tonight he inadvertently yanks the mic so hard it rips loose from the cord. This error, combined with an already tough room, ends up defining the rhythm of his set. White ditches most of his written material in favor of crowd work and this includes accosting a woman wearing an iPhone around her neck like its a VIP laminate and calling out a Swedish guy who is asleep in the front row. Exasperated by the ongoing silence he finally asks, “Is this an intervention?” White doesn’t win the crowd, but his indefatigable determination wins me.

The last time all this is on my mind is at a double billing at Zanies this past weekend co-headlined by Beth Stelling ("Conan"), a Chicago standup now crushing it in L.A., and the brilliant Drew Michael who is moving to New York this week. I expect only the best from these two pros. Michael opens with a topical reference to the World Series that provides a lead in to a few pointed jabs at sports nuts such as fans who wear the jerseys of their favorite player to the game. “[You wouldn’t] go into a Best Buy wearing a blue Kyle shirt,” he says. Think about that one. Stelling, meanwhile, also hits a home run. “I’ve been going around the country telling jokes and drinking beers,” she says at the top of her set. “I have no idea how many kids I have out there.”

As I pay my tab and shuffle out of Zanies I think about something Louis C.K. at the top of his 2009 live album Hilarious: “I never figured out how to come out and just start talking because the first thing you say onstage always feels stupid.” If the greatest working comic today still feels like an idiot when he first opens his mouth, that’s got to be good news for the rest of us, right?