The most celebrated American film critic of the century, of course. But just as important to this list, someone who wrote reviews that were equally accessible and compelling, insightful and understandable. Ebert towed the line between the art of criticism and the art of appealing to mainstream readers perfectly in a way that reflected the city around him. He possessed a dry wit that was not showy but was plenty cutting and scoffed at films that were overly pretentious without anything at their core. He was also an independent spirit who frequently went against grain of a movie's overall critical reception. A true Chicago original.
There have been writers from Chicago that were more popular on a national stage but Mike Royko was the quintessential chronicler of the city for over 40 years. Starting as a political reporter, Royko's penetrating and skeptical commentary earned him the admiration of readers and the hatred of city bosses (including Richard Daley, who Royko wrote an unauthorized biography of). Once his popularity was cemented, he was given a daily column which he used to comment on all aspects of Chicago life. Throughout his career he maintained an almost impossible work output for a writer. He also never lost touch with the culture of his hometown, helping to popularize his favorite haunt, Billy Goat Tavern, including the famous Billy Goat Curse, and frequently “conversing” with fictional blue-collar Chicagoan Slats Grobnik. Few people understood and loved Chicago like Mike Royko.