Lyndsay Hailey: Chicagoan of the Week


I am sitting at the Starbucks underneath Second City, a comedy landmark, wearing the hoodie that bears the name of my college improv troupe. Seated across from me is Lyndsay Hailey. She is smiling; I have gotten used to that. Lyndsay wields an infectious positivity that has suited her so well in an art that is notorious for depression behind closed doors and brilliant but bi-polar performers. I have a list of things that I want to discuss with her, but we are both improvisers. I decide to leave enough wiggle room, and try to make sure I am listening.

Lyndsay is a busy woman these days. Most days, really. Since moving to Chicago from Richmond, Virginia her life has been a consistent comedy cyclone. Lyndsay performs every Saturday at 8pm at iO in the Deltones, a completely improvised long-form show. She also plays with Armando at iO, which is sort of like an all-star game for improvisers, on Monday nights at 8:30pm. Saturdays she runs the Hangover Clinic and Tuesdays/Thursdays are improvadance. She is running a sketch show at the Fizz Bar sketch test all through November, and the music video she produced for her song “Balls” is currently in post-production. I asked her what she likes to do to unwind from all of her hard work. “Nothing. My down time is exactly that,” she replies. More on that later.

I have known Lyndsay longer than I have known almost anyone else in the city. She was my first teacher when I started classes at iO, and she still teaches there amidst her busy performance schedule. When it came time for some friends of mine to pick a coach for our team, she was our logical choice. Oh, did I mention? Lyndsay coaches outside teams. She uses her prowess for comedy and her knack for encouraging exploration to foster creativity in those who want to learn. Speaking of coaching, she also started the pilot improv section of After School Matters, an extra-curricular program for inner-city youth. Describing yourself as a homebody might not apply if you are never at home, and I can’t imagine how much time she has away from this community. But that is exactly why Lyndsay is here. I asked her how she got to Chicago from Richmond, and she couldn’t really say. All she knew is it kept coming up, the idea of improv, of doing comedy in Chicago. One day she packed up and moved. She said is was extremely difficult, because her entire family is in Richmond, but that “everything was pointing to Chicago”.

“You must get out sometime,” I prod, hoping for some juicy Chicago morsels I know nothing about. Finally I pull something out of her besides Law and Order SVU and Haagen Daaz: “I love thrift shopping & vintage clothes. I could probably tell you every thrift shop in the city.” Suddenly, as if yes-and-ing her admission, she is off like a shot. “Toro Sushi, go early; try the Chai Tea Latte at the Bourgeois Pig, I get at least one a day; south of Humboldt Park is a restaurant called Feed, best southern food in the city…” I cut her off at this point and shoot back with Smoque, my little BBQ nook on Pulaski. “I’ve never been,” Lyndsay admits. I tell her we’ll have to trade, as I have never tried Feed. Like any good improviser, she doesn’t drop her thought, and goes on: “The Green Mill off Lawrence has some of the best Jazz music, and old Al Capone stuff; Blues on Halsted, too, I take my dad there when he visits; any dance clubs where people actually want to dance, places like Berlin.” It seems that Lyndsay gets out after all.

Once in Chicago, Lyndsay wasted no time. She was put on an iO house team right out of classes and soon auditioned for the Deltones. She was also cast in an Annoyance Theatre show, “Love is Dead,” which ran for two years and won best music/lyrics at the Fringe Festival. Lyndsay has achieved so much, and without so much as a harsh word about anybody. Lyndsay tells me the same support taught on stage carries over to the social network in the Chicago comedy world. To her, the Chicago style of comedy is about honest relationships and exploration. Having studied on the East Coast myself, I know what she’s talking about. There is something so genuine about the community of performers in Chicago. People really want to learn the art. And Lyndsay has really learned the art. She has auditioned in front of Lorne Michaels, of SNL fame, twice in Chicago and has even been flown to New York for an SNL audition. I don’t know about you, but I have never spoke with someone that deep in the industry, let alone someone as kind and modest as Lyndsay. I am sure everyone wants to know how she did it, how she got to that point. Her answer might be maddening to those cut-throats, the people whose only goal is to climb the social ladder: “you can’t force the ‘how’.”

Here again is that bottomless well of optimism. “It would be a waste to compromise that pool of sincerity,” Lyndsay says of the people she has worked with in the city. “I have people who are willing to shoot my music video for free with their thousands of dollars of equipment. Why not do a show set in Chicago? We have an NBC here.” Lyndsay sees the path that so many people have taken; study in Chicago, move to New York or L.A. But you can’t argue with her credentials, or her smile.

Phil Kranyak

About Phil Kranyak

Phil grew up in small town in southeastern Pennsylvania. His family still lives across the street from a cornfield. Phil tried working at the farm when he was too young to get a real job and he left after one day because the farmhand was total creep city. He showed up to Phil's front door the next day wondering why he wasn't at work. Now Phil lives in Chicago and he thinks it was a pretty good choice.

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