2020 N. Oakley Ave. (2000N, 2300W)
Chicago IL 60647
"Home of free music in Chicago"
Though it's the only bar in Chicago I've ever seen with a Leinenkugel's sign hanging outside, Gallery Cabaret is a Certified Purveyor of the Miller High Life for its cheap drink specials (often Leinie's), ode to local artists inside and out, free food served often, and never a cover for nightly music and open-mic three days a week. This is why people love their favorite Bucktown dive bar, endearingly referred to as "GalCab" by regulars.
Gallery Cabaret is located at the southwest corner of Oakley & McLean Avenues, just north of Armitage and near Floyd's Pub, Charleston and Map Room. Gallery Cabaret is rather easy to spot with its bright red-painted brick façade and intriguing wooden sign hanging over the door with urban cityscape over minstrels proclaiming, "Spirits, Music, Art, Combos" (the latter being a jazz reference). An impressive series of graffiti murals are also found along the bar's northern exterior wall.
Step into the entry alcove and through the wooden door and you'll find a long barroom with black & white linoleum tile, a forest green-painted drop ceiling with many old-fashioned ceiling fans to dissipate the smoke that once collected thickly in the air before the smoking ban, and a long, linoleum-topped wooden bar that runs the length of the northern wall. A rotation of track-lit artwork hangs throughout the room. I once saw two paintings of a green woman with orange hair and, yes, the carpet matched the drapes... The owner and bartender Kenny also showcases a few of his works above the bar.
If you're lucky, grab one of the two black vinyl booths as you walk in, next to the Golden Tee, otherwise you'll want to snag one of the cocktail tables next to the restrooms, halfway down the southern wall. Otherwise, belly up towards the far end of the bar so that you can have a good view of the stage at the western end of the room where bands play on an elevated stage every night in front of a backdrop of the Hancock Building as if looking over the rowing lagoon in Lincoln Park. Like nearby Mutiny on Western Avenue, Gallery has a cabaret license, which means that music can be performed but only without charging cover. The stage at GalCab features indie rock, jazz, blues, horns, comedy, and open-mic every Tuesday, Thursday and Sunday night. Even Smashing Pumpkins, Urge Overkill, Material Issue, and Liz Phair all played here before they hit it big. When the band takes a break, music is played from a wall-mounted TouchTunes internet jukebox in-between sets.
GalCab features 14 beers on tap, 17 more in bottles and an eclectic array of spirits. They even serve glögg during winter, making them the only bar in addition to Simon's in Andersonville to serve this delectable, hot spiced wine. While there is no kitchen at Gallery Cabaret, they often feature, "Beer, Blues & Beef" on Wednesdays and a free buffet on Sundays. More importantly: both Arturo's Tacos and Lazo's Tacos (open 24 hours) are located just around the corner on Western.
"Sometimes you walk into a place and think to yourself 'REALLY!!! I CAN'T BELIVE THIS PLACE EXISTS!!!' It is amazing and breathtaking, with all the feel of your grandpa's basement hideaway if he had picked up painting later in life as a hobby."
– Mervin J. on Yelp (August 28, 2009)
What few Bohemians still living in Bucktown are probably found nightly at Gallery Cabaret, when not packing Charleston, along with the few of us in the know outside the neighborhood as this bar is hard to find with its somewhat obscure location. The mood is super chill, attracting a wide swath of humanity—I once saw two belly dancers walk out, and they weren't even performing!
Gallery Cabaret originally opened in 1990 by owner Ken Strandberg, whose intent was to harken back to a time when, "You could walk into a joint, buy a drink, and enjoy live entertainment like comedy or music just for being there and being a patron." As such, walking into Gallery Cabaret is like walking back in time... For more information, check out the Gallery Cabaret website.
"It took a while, but a few years back the management finally came around and started kicking out the truly crazy people and homeless guys who would crash out in the seats. The crowd scene is now more yuppie-friendly but most of those types are sucked into a nearby "pub" before they find the Gallery. Also, the folks who really appreciate the Gallery are mostly a diverse bunch of locals many of whom aren't failed musicians. The new crowd has managed to incorporate what I once loved only without all of the irritating factors. There are still few total jagoff regulars that come here, but they aren't too hard to spot and avoid."
– Erik R. on Yelp (August 9, 2006)