Sean Flannery
written by Michelle Peterson
Sean Flannery’s first jokes were delivered in the most literal sense — in a stamped and sealed envelope.
“My dad was a social worker with six kids, but he was a really old-school Catholic, so he made me go to this fancy Catholic school. The consequence — I mean, I really loved going there — but the consequence was that my friends ended up going to all these really great colleges across the U.S. So I started writing them letters in college,” Flannery said before a recent show. “I started writing them letters, just updating them on what I was doing, and they started sharing them with their roommates or fraternity brothers, and people really liked it. Then people started asking me to send them letters.”
His stories got passed around, and letters to friends evolved into an informal mailing list that turned his interest toward comedy.
“A lot of it was drinking stories,” said Flannery, “and I used to have a really bad job history. That always made my friends laugh and that’s when it occurred to me that I could make strangers laugh, too,” .
The show, the Visitor’s Locker Room Super Bowl Spectacular, was held at the Lincoln Lodge, a Twin-Peaksy underground comedy venue tucked away on Chicago’s north side. The show’s multi-media format is a good illustration of Flannery’s comedy direction: Six years after moving from Cleveland to Chicago, he’s worked his knack for storytelling – and skirting death – into stand-up, sketches, videos and podcasts.
Flannery’s letter-writing habits also changed with technology. Instead of a mailing list, he updates his blog with stories and insights, from likening beer muscles to “Google brain” and how not to treat your kid like a dog.
His most recent undertaking is an amalgamation of video, photos, storytelling and comedy.
“I tell a lot of drinking stories on stage, and I’m trying to combine them all into a multimedia play about all the times I should have been dead,” Flannery said.
He spent two months structuring the barebones of the play, and then spent three months learning the animation software.
“There’s this weird balance,” said Flannery, “I think there’s a lot of interesting things you can do with it all together, but you don’t want it to be some gimmick where people are laughing just because you have a crazy photo behind you,” I want to use it in a way that’s actually advancing the platform of a joke, rather than, ‘That’s a pretty hilarious photo of a fat person.’”
Flannery’s also featured on Blerds.com (that’s blogs + nerds = blerds), a group that fuses stand-up, humor blogs and video. Most of the videos layer a stand-up bit with staged reenactments to illustrate the story.
“I think there are a lot of interesting ways to combine stand-up with animation and video, and I’d like to do more of that,” Flannery said. “Just putting it on video or putting something on a blog doesn’t mean anything. I think there are a lot of people who think, ‘Get it online, man, and it’ll take care of itself,’ but it’s more than that.”
Drinking and near-death stories anchor his stand-up, but they’re chased with smart observations (pretty often about really dumb things).
“I don’t agree with most comics in that the audience isn’t smart enough to get them. I think stupid people stay home and watch ‘Wife Swap,’” he said.
Flannery produces and cohosts the online radio program Visitor’s Locker Room with the show’s creator and fellow comedian, C.J. Sullivan. (The Super Bowl Spectacular is a once-a-year gig tied into the show.) Together, with a lineup of regular guests, they lampoon over-the-top sports broadcasting, fans and professional athletes.
“Everyone watches sports, but you have to go through ESPN, which is this bombastic, ridiculous, terrible channel and no one’s really parodying that,” Flannery said. “No one’s catering to people who like sports but hate that part of it.”
Sullivan created the show three years ago with Pat Brice. Brice, a friend and fellow comedian, passed away unexpectedly a little more than a year ago but his presence is still strong in this circle of Chicago comedy. His parents, for example, came out to see the Super Bowl Spectacular, and mentions and photos of Brice are laced through his friends’ Web sites.
Visitor’s Locker Room airs live at 3 p.m. Tuesday through Friday from the Chicago-based Internet radio station Fearless Radio (www.fearlessradio.com). Flannery – unabashedly thankful that his employers are cool with his comedy schedule – leaves work at 2:30 p.m. on show days to meets CJ at the station. Sullivan, the more natural and avid sports fan, drives the show and Flannery co-hosts.
“Most of the work is actually in consuming sports stories: reading news aggregators, looking for unusual stories; watching ESPN or listening to sports talk for examples of ridiculous reporting,” Flannery said.
The two meet every Sunday night to map out the major stories and segments for the week. Then they exchange e-mails and update a private blog with different ideas throughout the week. There’s usually a second writing session Wednesday or Thursday.
“I have to admit, it’s easy for our writing sessions to blend into drinking sessions, so I shouldn’t act like its laborious work that I hate,” Flannery said.
They have a revolving lineup of great comics, from Chicago or formerly from Chicago, like T.J. Miller, Kyle Kinane and Matt Braugner. The show parodies over-the-top sports media, like ESPN and AM talk shows, and they also cover current events and tell some drinking stories.
“You don’t have to be real into sports to enjoy the show since, when we do talk about sports, we’re usually just ridiculing the people that are too into it,” Flannery said. “I’d say only about 60 percent of our fans are really into sports; the remaining listeners just enjoy the comedy but don’t follow sports outside of the show. I think, in some ways, it’s like a sports equivalent to The Daily Show, in that people who wouldn’t otherwise follow politics absorb some news because they enjoy the show’s comedy.”
Flannery and Sullivan also maintain a blog and other content at www.visitorslockerrom.com. (Fair warning: The site’s been a little wonky since less-than-smooth transition of their servers to a new studio. As of press time, a fix is in the works.)
He thinks the idea is pretty marketable, but Flannery didn’t get into stand-up to be famous. He just likes telling stories, meeting people and writing comedy. And he must enjoy it, because he stretches himself pretty thin to keep all his plates spinning: his wife Jessica and their toddler Colin, a full-time gig, four-day-a-week Internet radio show, regular stand-up and road shows.
“I don’t know if I’ve ever looked into why I like it so much,” Flannery said. “I just really like to laugh, and I kind of make myself laugh, and then you meet so many other people doing it that make you laugh.”
Flannery’s different than a lot of Chicago comics, especially the north side scene, which breeds a lot of middle-class-theater-geeks-turned-comedians. He comes from a blue-collar background, but in the traditional sense, he said, not the way its been “hijacked by hucksters who want to sell NASCAR CDs.” He’s always had a huge circle of friends and held fulltime jobs since he was 16.
“I’ve also lived my whole life like a guy who’s being continually diagnosed with six months to live, so I think the stories tend to be a lot different. There are probably a lot of comics who talk about drinking injuries, but very few who talk about being run over by their designated driver,” he said.
Dan Tefler, producer of Chicago Underground Comedy and fellow comic, sees Flannery at shows all over town – the scene here overlaps pretty regularly.
“Sean knows his own storytelling style very well, and adapts his material in such a way that audiences immediately connect with him. He has a natural confidence and bravado, but at the same time knows how funny it is when he has failed miserably,” Tefler said. “His humility and stage presence go perfectly together.”
“He’s most known to a lot of people for his work on the sports radio show Visitor’ Locker Room, so when I first watched him perform I was starting, he was in his stride, and I was intimidated by him,” he said. “I don’t like sports [and] jocks are who beat me up in high school. But he uses his powers for good.”
Flannery’s no niche comedian, though, Tefler said. “I now know him more for his material about getting married and having a kid, true to life stuff that I am also writing material about. And offstage he doesn’t have any of that huge, sometimes growling presentation. He is a very humble, normal guy who is a lot of fun to have a beer with,” Tefler said.
Chicago’s comedians aren’t desperately trying to seen or looking for instant notoriety, either. There’s a more painstaking pace to making a career out of it, thanks oftentimes to family obligations or the relative ease of living in a city that moves at a flyover pace. A lot of comics — Flannery included —talk a lot about moving to New York or L.A. eventually.
“This play is what’s really important to me, and I can do it here in Chicago where I sort of have credibility and people know me,” he said. “I love the scene here, but you do reach a point were you’re just sort of like … if you want to try and make more money, you just need to hit the road, which I don’t really think I want to do, or you go out there to New York and try to sell one of those ideas.”
For now, he’s focused on putting up his one-man show – he’s got a curtain date of May 4 at a special Chicago Underground show at the Beat Kitchen – and buying enough credibility as a comedian to eventually do what he wants.
“I want to be able to quit my day-job eventually and I just want to make a living doing what I love, and humor is something I’m very proud of,” he said. “I never got into comedy to be famous. I just love getting up there and sharing stories and jokes that make me laugh and make other people laugh. You just meet so many insane people, and I love insane people. Like, everyone you meet is insane. It’s ridiculous and I love that.”
Michelle Peterson is a writer from Chicago.
For more on Sean Flannery, visit www.WorldsDumbestMan.com.