Old Town Ale House

The History

Old Town Ale House opened in 1958 at 219 W North Avenue in Chicago's Old Town neighborhood, just steps from the Second City comedy theater. From the beginning, it was a bar for people who didn't want a fancy bar — artists, writers, comedians, musicians, neighborhood eccentrics, and anyone else who valued cheap drinks, good conversation, and a complete absence of pretension. The location was key: Old Town in the late 1950s and 1960s was Chicago's bohemian enclave, a neighborhood of folk music clubs, improv theaters, and the kind of creative energy that attracted people who didn't fit anywhere else. The Ale House became their headquarters.

The bar's most famous regular was Roger Ebert, the Pulitzer Prize-winning film critic of the Chicago Sun-Times. Ebert discovered the Ale House in the 1960s and never left. He drank there for decades, wrote about it extensively in his blog and memoirs, and declared it, flatly and without qualification, "the best bar in the world." Coming from a man who had been to every bar in the world, the endorsement carried weight. Ebert loved the Ale House for the same reasons everyone loves it: it was real. No craft cocktails, no artisanal anything, no carefully curated atmosphere. Just a bar, a jukebox, a collection of genuinely interesting people, and the sense that you had walked into a place that existed outside of time.

The bar is owned by Bruce Elliott, an artist and provocateur who has made the Ale House into a kind of ongoing installation piece. Elliott paints nude portraits of politicians, celebrities, and cultural figures — Donald Trump, Hillary Clinton, Barack Obama, local aldermen, neighborhood regulars — and hangs them behind the bar. The paintings are deliberately provocative, frequently hilarious, and absolutely unique to the Ale House. No other bar in America has anything like them. They're a statement of purpose: this is a place that refuses to take anything too seriously, least of all itself.

What Made It Famous

Roger Ebert's endorsement as "the best bar in the world" is the headline, but Old Town Ale House's real fame comes from its pure, uncompromising authenticity. In an era of craft cocktail bars with $18 drinks, exposed-brick interiors designed by consultants, and Instagram-friendly lighting, the Ale House remains a gloriously unreconstructed dive. The lighting is bad. The furniture is old. The bathrooms are an adventure. And that is exactly why people love it. The Ale House is proof that the best bars are not designed — they evolve, over decades, shaped by the people who drink in them and the owner who refuses to change them.

Bruce Elliott's nude paintings are the bar's visual signature, and they're unlike anything else in American bar culture. Seeing a naked painting of the current president hanging next to a naked painting of your neighbor is the kind of experience you simply cannot get anywhere else. Elliott paints constantly, adding new subjects as the political and cultural landscape shifts. The paintings are equal-opportunity in their irreverence — left, right, famous, anonymous, everyone gets the same treatment. They're a reminder that at the Ale House, nobody is more important than anyone else, and everyone is fair game.

The proximity to Second City means that generations of comedians have made the Ale House their after-show watering hole. John Belushi drank here in the 1970s, before he became the biggest comedy star in the world. Bill Murray drank here. Tina Fey, Amy Poehler, and Steve Carell all passed through during their Second City years. The current cast still comes in after shows. The jukebox is legendary — a curated selection that somehow manages to be both eclectic and perfect, reflecting the tastes of the artists, writers, and weirdos who have fed it quarters for over six decades. The Ale House is not just a bar; it's a living archive of Chicago's creative soul.

Key Facts

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