“A Chicago Tavern Classic”

Photo courtesy of Jeremy BilesIf your crazy uncle opened a bar, it would be the Charleston. Even with its gothic decorations and feel, it is a classic neighborhood bar – a classic Wicker Park neighborhood bar, that is, which would make it an eclectic Bohemian hangout anywhere else.As you walk up the steps, under the homemade Charleston sign, you are greeted by a bizarre sculpture of a reptilian women with massive thighs wielding a sword in the front window (this has replaced the stuffed goat named Juan that used to be propped up by a stuffed armadillo – thankfully, the armadillo remains). Inside, you will find a dark wooden bar that runs along the south wall, a second hand store’s variety of tables and chairs, a linoleum floor, a lamp made out of a ram’s head, coasters claiming “We’re glad you’re here!”, stuffed ducks in mid-flight, photographs by locals on the wall, a stuffed swordfish adorned with red string lights with the sword part broken off, and a regulation size pool table in the back. Behind the bar, you will see a large mirror and several carved versions of Cupid, the one in the center of the bar being the same one printed on their sign and matchbooks. To the left of the bar is a framed poster-sized photograph of Fidel Castro and what looks like Jerry Garcia. The bar offers 10 beers on tap and at least twice that many in an old-fashioned, wood paneled cooler. American beer connoisseurs will appreciate the availability of Schlitz and Pabst. The men’s bathroom is located in a wooden closet at the west end of the bar, which I originally discovered only by process of elimination due to poor labeling and even poorer eyesight.

The middle of Charleston is where a variety of acoustic folk, jazz musicians and alternative bands play regularly, some of which utilize the upright piano and the powered Mackie mixer above it (next to the upside-down mannequin legs. During the Winter of 2000-2001, I observed two giant paper maché tree branches jutting out into the middle of the room and Christmas lights in the shape of little green Christmas trees. This effect was complimented by a winter scene on the back wall lit by blue Christmas lights.

On New Year’s Eve 2001, after a traditional lunch of Mexican food at Tecalitlan on Chicago Avenue, a few friends and I rolled into Charleston only to find the eerie tree replaced with a much smaller Christmas tree, adorned with red cardinal lights, and a jovial Santa Claus. The interesting thing about this particular Santa was that he was stretched along the length of the entire bar, on the ceiling, and his giant head hung upside down along the back wall with a gas meter for one of his eyes. The surroundings were perfect for enjoying several pints of Guinness and a few shots to warm ourselves up for the festivities had later at Subterranean. Talk then turned to a man that was once observed in Barcelona wiping his bum with the world.

Photos courtesy of Lorilea

Photo courtesy of Jeremy BilesThe Charleston bills itself as an old-fashioned bar: no televisions, pay phone, Golden Tee, pinball, or any other machine that is coin operated. When you play pool, just make sure you deposit your $0.50 in the metal can on the side – it’s on the honor system. A small label with “PAY” written on it, reminds you to do so on the triangle. Normally, you’ll see locals reading newspapers during the day and Monday night is movie night.

The pool area is the source of many interesting adventures. One night an exceedingly drunk, obnoxious woman was taunting competition while claiming to be the best friend of the wife of the man she was with (follow that). This woman and her man-friend were run from the table by the friendly pool sharks that hit the scene around 10:00 p.m. All of this was observed by a man perched on a stool that looked like the Gordon’s fisherman, sans slicker. And here’s a tip: if you’re playing pool and need to use the short boy, use the longer of the two they have available.

On New Year’s Eve 2000, I had a spanking good time at Charleston while drinking Guinness all afternoon while watching all the New Year’s celebrations taking place all over Europe. The Charleston is exactly like that – the kind of place where one can enjoy hanging out in a very relaxed environment that is extremely conducive for conversation. I was even given a free round of drinks on New Year’s Eve 2002 when after the bartender sternly told me that cigar smoking was not permitted. In one such conversation at the Charleston, I learned about the almost fictional game of “Smiles.” I say almost fictional because for most guys it’s a fantasy, but for the one I talked to it actually happened. To play, all you need is a bunch of guys sitting at a table and a girl (preferably naked). Each guy then takes down his pants so that he is completely naked from the waist down. The girl, unseen under the table, proceeds to please one of the guys and all the others have to try to see if they can tell who is getting the action – especially by watching to see who smiles. Once the game was over in this case, the still naked girl was then invited to play basketball, which she did.

Writers of the Official Chicago Bar Guide (1994) describes, “So homey, a cat fell asleep on our lap while we wrote the review,” and “Precisely the reason folks move to Bucktown,” (2001). Since opening in 1986, when the neighborhood was still rough, owner Wendy Pick has made Charleston one of the best bars in Bucktown and just strange enough to hold your interest and keep you searching the room for new, previously unseen oddities. And let’s keep our fingers crossed they get the boa back, which was stolen from Juan. For more information (kind of), check out the Charleston website. Keep on smilin’.