Photo via Funny Business Agency
Comedy may not offer salvation, but it can provide direction. For Jim Flannigan, that direction can become a vocation.
“I was drifting through my early 20s aimlessly, and I needed a focus outside of work and hanging out with my friends,” the Chicago comic recollects, “and stand up became it; but I never really thought it would go anywhere. It started off as just a hobby, and then, one day, it had just become a huge part of who I am. Plus, they give you free drinks.”
Flannigan perform at 8 and 10:15 p.m. Saturday, May 1 for live and livestreaming audiences at The Laughing Tap (706B S. 5th St.; 885-0129) and the seats filled for the latest edition of Keg Stand Up at Lakefront Brewery (1872 North Commerce St.; 372-8800) at 6 and 8:30 p.m. At Lakefront, Flannigan will join Darrel Cochran and Katie Meiners in opening for headliner Joe Fernandez. And if that seems like a high comedic workload for one man in a weekend, it's no big deal to Flannigan.
“In a city like Chicago, you grab stage time wherever you can, so this isn’t unique to me at all in that respect,” he explains, but he notes how the two gigs put him in varying positions. “There’s different pressure in the different roles. Saturday, it’s my show and I’m really excited to headline the Laughing Tap for the first time and bring people into my world. Milwaukee Comedy was awesome to let me stick around and do spots on the Lakefront shows on Sunday. Joe Fernandez and Katie Meiners are two of my favorite comedians, so there’s no pressure and I can take different risks in this spot.”
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Laughter is a Family Business
The business side of comedy can be less exciting than the act of making people laugh, but for Flannigan, it kind of runs in the family. “My dad sold irrigation and would take me with him to sales calls at a young age and there’s a huge crossover between the two. So much of the business side of comedy is very similar to sales in that you have to be engaging, build relationships, manage a calendar, and so much more. He also had the best sense of humor and always had a joke to break the ice.” So comfortable is Flannigan in the business world that he became a co-cost of the Brew Your Skill video serie, offering advice and inspiration for entrepreneurs and managers. And if Flannigan isn’t killing on comedy club stages, he could be plying his gifts at corporate events.
As to insinuating himself into that scene, he says, “I tend to work cleaner, but not exactly clean, so my act can translate to the corporate world. I’ve been lucky in that people who have seen me in clubs thought I would be good for corporate events, so they booked me; and it started growing from there. I think the most important thing is just being relatable and as I get older, unfortunately I am probably more relatable to 40-year-olds than college students.”
Finding Inspiration
Flannigan’s mother played a part in her son’s comedic development, too. “My mom also has a great sense of humor and introduced me to stand up as an art form. As a kid, we would listen to Bill Cosby records and watch stand up on TV like ‘Comic Strip Live.’” When it came to the lodestar for his comedy persona, though, Flannigan points to Dave Attell.
“There was just something different about his comedy that I had never seen,” he says of his hero. “It’s dark and personal and clever and irreverent, such a departure from the brick wall comedy of the ‘80s and it just spoke to me in a way that comedy never had before. I think that’s when I started to realize that there's no right or wrong way to do this, as long as you're yourself.” Apart from his dates in comedy clubs and the corporate milieu, Flannigan expresses himself for public consumption by co-anchoring a pair of weekly podcasts: the thoroughly random All Over The Place with Pat McGann and What Do We Know? wherein Flannigan and Hari Rao discuss fields of endeavor about which they don't know much and learn about them from their guests.
As for expressing himself in this weekend’s performances, the relaxation of the COVID-19 has Flannigan stoked to be back in his element. “This weekend is going to be special. These lineups are stacked with great comics and we're all dying to get out there and connect with audiences again.” And though he’s complimentary of online performance—"I really ended up enjoying some Zoom shows, if the audience have cameras and microphones on”—he knows there’s no substitute for actual human contact.
“You want to watch a stand-up comic do bits online? Great. There’s YouTube, and there’s a laugh track and everything!”
Here Flannigan speaks of his bald spot, something to which the 40-year-olds who see him may relate better than the collegians:
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