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SIDETRACK: The little bar that could.
When it opened in 1982 many folks thought that Sidetrack’s concept was a foolish one. A video bar? Who’ll want to go to a bar to watch television? Sidetrack was one of the first video bars in the country, certainly the first gay video bar in Chicago.
The folks behind Sidetrack were true pioneers. Keep in mind that MTV and other music video stations were in their infancy at that time. With a less than stellar selection of videos available at the time, Pepe and the other VJs often created their own, which eventually developed into Sidetrack’s signature style.
Over the years, Sidetrack has grown from one room with less than 1000 square feet to a collection of spaces spanning more than eight storefronts and multiple levels and can now host more than 1000 people at a time. Sidetrack was recently named one of the best gay bars in the world by Out.com. Here’s how they did it:

1984 The bar expands to include the next storefront to the north, doubling in size. A white tile façade is installed, still without an exterior sign.
1988 The first version of the BackBar opens, it is a three season space, with pull-down garage doors as walls.
1994 Sidetrack expands another storefront north. The new addition is dubbed “CherryBar” because of the predominate wood used for décor, overlooks the main bar. A small sign and a window on Halsted opens up the space for the first time.
1998 The BackBar is remodeled and insulated for year-round use.
1999 The property expands another storefront space, this time to the south. Replacing the Gallimaufrey Gallery (which moved to Lincoln Square), the new space is dubbed GlassBar” for the wall of windows facing a courtyard, which becomes the bar’s main entrance. A stainless steel kiosk with the bar’s name is featured.
2001 Expanding another storefront to the north, replacing a laundromat, allows for the expansion of CherryBar with CherryLounge. Behind the scenes, a new video production facility, expanded storage and offices are added.

2007 The CherryLounge is expanded even further.
2009 Expanding another storefront to the south allows for the installation of an expanded coat check, an expanded video production center and the cozy SideBar, which features access to courtyard.
Over the years Sidetrack has hosted a variety of events that have become local traditions. Among these are; “Night of 100 drag Queens”, Mardi Gras, a chili cook-off and wine tasting parties, in addition to the monthly “First Friday” cocktail party to benefit Equality Illinois.
There probably isn’t a not-for-profit associated with our community that hasn’t held a benefit at Sidetrack, which accounts, in some part, for their extreme customer loyalty. Finally, if you want to avoid looking like a rube, remember there is no “S” at the end of the bar’s name. It’s not “Sidetracks”; it is Sidetrack, plain and simple. And successful
A LARGER COCKTAIL , PLEASE
Cocktail, is one of the most inviting, playful bars in Lakeview, appealing to a broad-based clientele that is short on attitude and long on fun. Not too log ago, the bar was remodeled. The front room, with window seats that provide a panoramic view of Halsted, features black crystal chandeliers, an onyx-lit bar imported from Greece. Away from the windows, the scene gets a bit more lively, thanks in large part to a stage area that hosts the “Spank Go-Go Boys” five nights a week and a DJ.
Not content to rest on its design laurels, Cocktail is expanding into the space formerly occupied by the quirky pizza palace, Pie Hole. This intimate space will feature a second bar, and black crystal chandeliers, gold leafed ceiling and a fireplace. The name of the back room remains a mystery at this point, but it will be able to be reserved for private parties and has a separate sound system allowing for the bar’s music to flow from room to room or be site specific.
In addition to the interior expansion, there is an addition to the exterior as well. The sidewalk along the side of the bar facing Roscoe will be flanked by an outdoor patio, aka, “The Garden.” English box hedges will establish an urban oasis featuring modern furniture for a lounge area that will include table seating.
Those tables will come in handy as the aptly named Erin Baker takes over food management. The menu will be small, but formidable. Among the offerings will be a trio of sandwiches and salads, as well as house made ice cream. A garden Party brunch will be held each weekend staring at 11:00. All or most of these changes should be in place by the time this issue of boi hits the streets.