A self-proclaimed dive, Old Town Ale House doles out drinks until just before dawn in a dim, often-cramped space that exudes an enticing dinginess. Its proximity to Piper's Alley--home to The Second City--as well as to Zanie's Comedy Club and the Orchid Theater almost guarantees a steady crowd of performers and theatergoers who sidle up to the cash-only bar for beers on tap, shots, and cocktails. There’s not a lot of fuss here, but that’s where its charm comes from. The bar is cash-only and a bag of chips is the only available entrée option. Even the jukebox is filled with old-timey crooner tunes and jazz. It’s the type of music that was appreciated by the hotshot newspaper reporters, such as Roger Ebert, that called this place their late-night haunt of choice and their preferred spot to duck in during killer-bee attacks.
Portraits of famous faces stare down from the walls, frozen in pigment by artist Bruce Elliott, whose paintings depict notable Chicagoans, Second City alums, and naked women in equal measure. Visitors can check out renditions of famous Old Town Ale House regulars, such as John Candy and Jim Belushi, and also ogle at paintings that have garnered national attention, such as nudes of Sarah Palin and Rod Blagojevich. Mr. Elliot is not only the bar’s interior decorator, he’s also the one running the show. Mr. Elliot befriended longtime owner Beatrice Klug over the more than four decades that he was a regular at the bar, and she decided to hand over the keys to the joint after she fell ill with cancer. Beatrice bequeathed Old Town Ale House to Mr. Elliot and his wife under the condition that they would not make any changes. Since opening in 1958, Old Town Ale House continues to remain suspended in time.