He has also written seven books on topics ranging from movies to urban legends to conspiracy theories to the Chicago White Sox.

In 2009, Roeper appeared on Howard Stern's show and said he had written a book on gambling, entitled Bet the House,[8] which was released in the first quarter of 2010.

He also hosted shows on WLUP-FM, WLS-FM, and WMVP-AM in Chicago.In the early 2000s, he was the film critic for CBS in Chicago for three years.

Roeper has written for a number of magazines, including Esquire, Spy, TV Guide, Playboy, Maxim, and Entertainment Weekly.

[9] Roeper has been a frequent guest on The Tonight Show, Live with Regis and Kelly, The O'Reilly Factor, and countless other national programs.

[11] In February 2009, Roeper launched his website, which features movie reviews, blog entries, photos, and Twitter posts.

[15] On February 2, the Sun-Times released a statement stating that their investigation did find that Roeper purchased over 25,000 fake followers.

[18] After ten appearances on the program,[19] Roeper was offered the opportunity to co-host the popular film review show with Ebert permanently.

[7][21][22] Beginning in August 2006, while his co-host Roger Ebert was recovering from cancer surgery,[23] Roeper was joined by numerous guest critics, including Clerks director Kevin Smith, The Tonight Show host Jay Leno, and singer-songwriter John Mellencamp.

On September 12, 2013, it was announced that Roeper will replace Roger Ebert as the main movie critic for the Chicago Sun-Times after his death on April 4, 2013 at the age of 70.

[26] In August 2014, Roeper became first-string film critic for the Chicago Sun-Times, where he made his debut reviewing Guardians of the Galaxy.

[28] Roeper has cited The Maltese Falcon, The Godfather trilogy, and Ferris Bueller's Day Off as among his favorite films.