Roeper was born in Chicago, Illinois. He graduated from Illinois State University in 1982 and began working as a columnist for the Chicago Sun-Times in 1987. The topics of his columns range from politics to media to entertainment, and he has written several books on film criticism and urban myths.
After Gene Siskel, of Siskel & Ebert, passed away in 1999, Roeper was offered the opportunity to co-host the popular film review show with fellow Chicago Sun-Times columnist Roger Ebert. The show benefitted from Ebert and Roeper's chemistry and often heated debates after several months of rotating co-hosts. The show was shortly thereafter renamed Ebert & Roeper.