Bruce Elliott started drinking at the Old Town Ale House in 1961, three years after it opened. Back then, the place was hoity-toity and played classical music. After it burned down and reopened across the street, the crowd got rougher, but Elliott kept going. He liked to paint raunchy pictures, and soon they were hanging on the bar’s walls. Today the Old Town and its most faithful barfly are a living connection to a long-gone version of Chicago, one where the drinks were cheap and the regulars were weird as hell. And here’s the best part: For the past 12 years, Elliott has owned the joint. Which just goes to show you, he says: “If you drink at a bar long enough, they’ll eventually give it to you.”