© The Chicago Bar Project
Written by Sean Parnell

The Redhead is a classic piano bar and, if not the most popular, it is certainly the most recognized in Chicago, even when you consider stiff competition from Coq d'Or, the Back Room, Zebra Lounge, and Davenport's.

For those "appropriately attired" (even the busboys wear white shirts and bowties), the Redhead is not hard to find. Just head to River North and look for the large white blinking sign with a winking, redheaded woman on it. While the woman looks like a naughty version of Daphne from Scooby-Doo, the bar was actually named after the former owner Eileen Wolcoff. Step through the wrought iron gate, under the red canopy, and walk down a few stairs to this red cocktail chamber – dark, yet inviting.

As you walk through the wooden-framed, plate glass door, you will encounter a polite yet critically observant doorman clad in a tuxedo, red bowtie and red cummerbund that serves almost more in a maitre'd's capacity. While he is pleasantly mannered, be sure that you'll be refused if you are not dressed nicely. I have worn jeans and a pair of Vans in there before, but that was definitely pushing it. My recommendation: wear pants and a collar.

Once inside, you will notice a piano on your left-hand side, surrounded by a horseshoe-shaped counter and located in front of the windows overlooking Ontario Street. Recently, I took in some piano playing by the burliest piano player I've ever seen, but the music was good and the atmosphere pleasantly loungey. There is a different piano player every night of the week, so come back often and you won't be bored, particularly as the music ranges from pop to jazz, rock to blues. If you feel like making a request, try to be more creative than Piano Man, Daniel, Sweet Caroline, or American Pie and remember to put a tip in the requisite giant bourbon glass / jar before the song. The Redhead never charges a cover.

There is a nice cherry wood, rectangular bar in the middle of the room, which is decorated with red paint, framed sheet music, and hundreds of photographs of actors that have never visited the Redhead (it's only been in business for 10 years). On one night I was there, there was an authentic redheaded women bartender, complete with standard Redhead Piano Bar attire: white tuxedo shirt, red cummerbund, and red bowtie as well as a red pen light to highlight the drinks menu. She also had red pens to write with and the check came with that ubiquitous saucy Redhead logo.

While beer lovers may be disappointed by the lack of microbrews (except for the token Sam Adams), martini connoisseurs will revel in their imaginative selection of over 20 martinis. These martinis include "The Redhead" (surprise), the "Madhattan," "Wendi's Dark Side," and "Madame Rouge." The Redhead also boasts a fine selection of red and white wine, champagne, cognac, port, bourbon, tequila, and single-malt Scotch. Everyone will appreciate the many bowls of Chex mix on the bar, which help stimulate your thirst. Cigar aficionados will be pleased with a selection of 16 different cigars to choose from (including the chocolate variety), located in a glass case in the back. You can't miss the case, as it is located next to the bathrooms and the brightly lit Redhead merchandise case filled with baseball hats, jackets and t-shirts for the cheesiest of tourists. On the way to the bathrooms and the cases, I noticed a curious nook with a brass plate signifying it as "Booth #2." Strangely, the Redhead has no booths – only tables – of which one of them was stuck into this alcove. Hmmm... Also of note was a cordoned-off area in the front of the room that looks like they are still waiting for Al Capone to arrive.

The crowd consists mainly of well-to-do middle age types that are either couples, conventioneers, tourists, older men taking out their daughters (or girlfriends of their daughter's age), and some swanky after-work types looking for a cocktail following dinner. The Redhead is rather small, so if you want a seat at the piano or the bar, get their early (the bar opens at 7:00 p.m.) Lounge lizards take note: The Redhead closes at 4:00 a.m. Sunday through Friday, and 5:00 a.m. on Saturday; an environment suitable to pick up someone either twice your age or half of it. Also seen was a waitress that looked like she was wearing a men's blazer, red bow tie, nylons and nothing else. Swing, baby.

"The Redhead Piano Bar is not the place to go if you're alone. That is, if you want to sit by yourself and just enjoy the music. If you want to meet an expense-account-bruising, traveling businessman, that's another story."

– Shelly Ridenour, excerpt from "Meet the dudes who croon the tunes" appearing in New City Chicago (1998)

Formerly known as Outtakes and the Fish Head (an alternative reggae bar), the Redhead has proven itself a worthy tenant of a great bar, even though they decided to get rid of the 900 gallon fish tank that made up part of the bar. For more information on The Redhead, or to buy an authentic Redhead t-shirt, check out the Redhead Piano Bar's website. Fans of the Redhead may appreciate the painting Piano Bar by Anne Aderman. Additionally, don't confuse the Redhead with Redhead II (Eileen Wolcoff's new bar, located at 42 E. Superior), which instead of a piano bar is an "ultralounge" – a story for another day.