Little Jim’s Tavern Is Big on History Forty-five years on, the Boystown mainstay is an intergenerational mosaic of Chicago’s gay community. June 27, 2019, 8:00 am Little Jim's Tavern (3501 N. Halsted St.) is Boystown's oldest extant gay bar. According to general manager Jeff Shand, the bar replaced a shuttered grocery store on the street corner in 1974, back when the neighborhood was still known as "New Town."Photo: Pat Nabong Al Treb, 94, poses in front of two portraits of himself taken decades ago, which are displayed on the bar’s wall. Treb attended Little Jim's opening night in 1974.Photo: Pat Nabong Treb knit the rug that hangs on the wall of Little Jim’s. He made it for Jim Gates, the original owner of the bar.Photo: Pat Nabong Big Jim’s, a newer bar connected to the original storefront, is decorated with pictures and memorabilia that evoke old Chicago.Photo: Pat Nabong Longtime customers chat over a drink while people pass by on Halsted. Originally, you couldn't see through Little Jim’s windows for safety reasons. “In the '70s and '80s, [the bar was] very dark," Shand says. "The windows [were] almost painted out, and [when] the police came into the bar, you couldn't hold hands. Little Jim's kept it dark to keep them away."Photo: Pat Nabong The bar's longevity makes it a popular attraction for visitors and returnees. "[Customers] go, ‘Wow, I remember this place. I came here when I was 20 years old; I met my lover here,'" Shand says. "Some of [the couples] met here and have been together for 32 years."Photo: Pat Nabong Cody Knight, Ben Windholz, Kate Ambrose, and Will Silberman visit the bar for the first time. “It's really interesting how they pay homage to the history here but still maintain a modern sensibility,” Windholz says.Photo: Pat Nabong Big Jim’s offers more space to dance than the adjacent Little Jim’s.Photo: Pat Nabong David Waymer and his partner steal a kiss.Photo: Pat Nabong A rare quiet moment at the bar.Photo: Pat Nabong