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Booker Ryan Ehresman, Town Hall Pub bartender Chris Robles, and DJ-about-town Rich Cole (aka DJRC) came up with the Flipside concept early in the summer; Ehresman says he was inspired by parties he went to in college where people would play tunes off their iPods. "I just upgraded [it]," he says.
Considering it's a vinyl-only affair, Ehresman, Robles, and Cole initially thought the Flipside could be more than just a gussied-up iPod party. "We joked around about it being a hipster date night," Ehresman says. He initially envisioned attendees comparing their records, trading insights about favorite bands, and maybe even exchanging numbers at the end of the evening.
No one exchanged numbers when the trio debuted the Flipside back in July—at least not to Ehresman's knowledge—but Ehresman was nonetheless happy with the event and the tunes pumping out of the PA. Ehresman brought a Benny Goodman album to kick off the evening, Cole played some Brazilian music, and Michael Jackson's Off the Wall got plenty of play time.
It all sounds like an unusual playlist for the evening, but Ehresman is drawn to trying out unconventional things in a live setting. Last September Ehresman presented his first show, the live debut of Willis Earl Beal's short-lived Ghostones project; comedian Dereck Smith emceed the concert and tested out his routine between musical performances. At times it felt as though Smith's act just didn't work with the bands on the bill, which is part of what made that event so memorable. Ehresman wants people to "get the fuck out of your comfort zone once in a while," and he's got a pretty good vision of how to curate events that toy with attendees' expectations and make it fun.
Ehresman has been putting on events at bars all around Chicago—including weekly Breaking Bad viewing parties at Lakeview's Holiday Club he organized with his girlfriend during the show's fifth season—and recently landed a regular booking gig at Lincoln Square's Horseshoe. ("I walked in and got the job of my dreams," he says.) He says he hopes to turn the Flipside into a monthly party, but for the time being Saturday's event is the only one scheduled, and it all starts at 9 PM. Don't forget to bring your little black book—it is, after all, a night dedicated to analog.