At first glance, Pat Whalen is exactly what you'd expect from a late-night talk show host. The 29-year-old is a white man with thick-rimmed glasses who puts on a black suit and skinny tie for his monthly comedic talk show, Good Evening With Pat Whalen. The self-described "late-night talk-show news-alternative" is like the love child of Conan and The Daily Show: the bits are quick and silly, the coverage has a political bent, and there's almost always a musical guest. What's unexpected is the lineup of people Whalen has brought on during the last two years. The actor and comedian has interviewed members of Black Youth Project 100; Ra Joy, the executive director of CHANGE Illinois; and Debra Shore, a commissioner for the Metropolitan Water Reclamation District. It's not exactly a group that screams laugh riot.
"People who deal with these serious issues want to be seen in a light that isn't so serious," Whalen says. "They're people. They like to laugh and go out on a Friday night too."
Since 2014 Whalen and his team have hosted Good Evening on the first Friday of every month at Edgewater's Frontier theater, hoping to inspire social and political change through entertainment. The show, episodes of which are also filmed and posted online, features comedic monologues and sketches as well as conversations with some of the city's most prominent movers and shakers.
But after two years of cramming into the Frontier's 45-seat theater, Good Evening is expanding, starting with a special free show at Truman College on Saturday, May 14, as part of Uptown Saturday Nights (a ticket normally runs $10). In addition to an interview with playwright Ike Holter and a musical performance by Chicago standbys White Mystery, the evening will include a pretaped sit-down with 46th Ward alderman James Cappleman.
"We're going to address what, unfortunately, some people associate with Uptown, which is violence and homelessness," Whalen says. "How the hell are we going to talk about this without stepping on the alderman's toes? Walk into his office and ask for his help."
It's a tactic Whalen uses often—his flexible day jobs as an actor and Uber driver allow him the time to put on his best suit and "show up where I'm not supposed to be." One such place is City Hall, where he'll spend hours standing around just waiting to get face time with aldermen, city officials, or anyone who has something to say about the current state of Chicago. Once people realize he's serious about what he does, they're usually OK with coming on the show, Whalen says, and are more worried about being entertaining than anything else. "I tell them, 'It's my job to make it funny, you just be yourself.'" But he does have a list of dream guests who have yet to get on board, such as Governor Bruce Rauner, artist Theaster Gates, and blogger Samantha Irby (the Reader's own Ben Joravsky also makes the list).
It's not lost on Whalen that he's yet another straight, white male trying to penetrate the world of late-night comedy. "The Pat Whalen White-Privilege Guilt Show doesn't really roll off the tongue," Whalen jokes. He makes a point of diversifying his lineup to accurately reflect the makeup of Chicago's population—the idea of too many white men on one show's lineup "haunts my dreams," he says. A new phase of that effort starts with the Uptown show, which he hopes to be one of many neighborhood-specific one-offs.
In the meantime, Good Evening continues its monthly run at the Frontier until it finds a new home in a bigger space for bigger guests. "I'm patient, and in the past two years I've seen it grow in a way that surprises me, big time," Whalen says. "The goal is to be the late-night talk show of Chicago." v