Luck of the Irish: Sean Flannery Has Lived Through Ten Near-Death Experiences And Still Manages To Laugh

Sean Flannery has had an unusual life, one in which he’s faced down hilarious near-death situations and managed to survive. He’s driven a car off one highway at seventy miles-per-hour during a blizzard, careened down a ravine and wound up landing perfectly on another highway below.

He’s also electrocuted himself at a job interview, fallen off a three-story rooftop at a Huey Lewis and the News concert, and attended the wrong wedding twice. And that’s just the tip of the iceberg, as he’s spent the past decade hosting the weekly comic storytelling show “The Blackout Diaries,” in which he’s shared countless stories of being drunk in embarrassing situations.

Flannery will be one of six comics taking the stage March 17 and 18 for the “Shamrock Shenanigans” shows at the Den Theatre with Irish comics detailing unique life experiences as part of a weekend celebrating St. Patrick’s Day. Also featuring Adam Burke, Jeannie Doogan (March 17 only), Chelsea Hood (March 18 only), Joe Kilgallon and Kristen Toomey, the shows will offer an ideal mix of booze and merriment—including green beer, naturally—with drink specials galore for the weekend.

“I’ve done a lot of Irish shows, some at the Irish Heritage Center, some at comedy clubs,” Flannery says. “I prefer to do them at clubs because at an Irish theater, they never let you use the actual theater building because they don’t want beer in their gorgeous theater. You think ‘Oh, this show is going to be great,’ but then you’re performing in a tent. With the Den having undergone some really awesome renovations recently, this is a perfect spot for the show.”

The forty-six-year-old Flannery grew up in an almost stereotypically large Irish Catholic family in which six kids were forced to compete for bed space in a two-bedroom home. His funny recollections about his family and the one he fathers now—with his wife of seventeen years and three kids ages fifteen, twelve and ten—comprise about half of his act.

But it’s the other half that has brought him notoriety on the city’s comedy scene, with his tales of drunkenness as he has hosted a weekly show called “The Blackout Diaries” on Friday nights for ten years at the Lincoln Lodge. The show gives him a terrific opportunity to meet all sorts of Chicagoans in a hilariously unique way.

“I’m proudest of ‘Blackout Diaries’ because it’s everyday Chicago drinking stories. I’ve gotten to meet teachers, nurses, cops, firefighters and just a lot of really interesting people,” says Flannery. “And it really makes you happy to live in Chicago when you just see how many people have a great sense of humor in this city and have all these great stories.”

Stories have always been key to his career in comedy, as his inspiration to pursue the art form came from an extensive series of letters he wrote his best hometown friends about his college exploits. Crafted in a pre-internet age, Flannery grew popular through old-fashioned methodology.

“When my friends scattered across the U.S. at different colleges, I would just keep in touch with them by physical letters,” he says. “Telling them funny stories that had happened to me recently, and it started with a collection of twenty friends at various colleges.

“They started passing them around at fraternities and so on, and then these strangers would write me back asking me to mail my letters to them. I started this mailing list that was just kind of a game and then I got it in my head that I seemed to be pretty good at making people laugh. I eventually went to open mics, I took a comedy class, too, and then I never looked back.”

Sean Flannery performs in the “Shamrock Shenanigans” shows March 17-18 at 7:30pm on Friday and 7:15pm and 9:30pm on Saturday at the Den Theatre, 1331 North Milwaukee. $25, thedentheater.com, (773)697-3830.