Roeper began working as a columnist for the Chicago Sun-Times in 1987. The topics of his columns range from politics to media to entertainment. In more recent years, he has been widely considered one of the finest newspaper writers in Chicago, just a notch below the city’s golden-inked “Mount Rushmore” of John Kass (Tribune), Dave Hoekstra (Sun-Times), Jay Mariotti (Sun-Times) and Roger Ebert (Sun-Times).