Roeper joined the
Chicago Sun-Times as an editorial assistant in the features department in 1986. He initially did freelancing columns before advancing to his role as a news reporter. In his early years, Roeper covered a range of general news and local events, while developing a particular focus on sports, including extensive reporting on the Chicago White Sox that reflected his lifelong fandom. His assignments as a cityside reporter involved shifting between beats to build a broad understanding of Chicago, encompassing everything from neighborhood changes to cultural happenings, which honed his observational skills. which was released in the first quarter of 2010. Roeper was a radio host on
WLS AM 890 in Chicago. 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. His columns have been syndicated by
The New York Times to worldwide publications. Roeper has written for a number of magazines, including
Esquire,
Spy,
TV Guide,
Playboy,
Maxim, and
Entertainment Weekly. In 2001, he was named one of
People magazine's most eligible bachelors. Roeper has been a frequent guest on
The Tonight Show,
Live with Regis and Kelly, ''
The O'Reilly Factor, and countless other national programs. He also hosted Starz Inside
, a monthly documentary series that aired on the Starz network. Roeper appeared on the first episode of the fifth season of Entourage, where he reviewed a fake movie titled Medellin
with Michael Phillips on At the Movies. In April 2008, Roeper was the central figure on an episode of Top Chef'', where contestants served up movie-themed dishes to Roeper and his friends (including
Aisha Tyler). In February 2009, Roeper launched his website, which features movie reviews, blog entries, photos, and
Twitter posts. In December 2009, he launched a video section that featured on-camera reviews of movies. The video segments were originally produced in partnership with the Starz premium cable channel. Beginning in December 2010, Roeper began producing video reviews for ReelzChannel. He stopped reviewing movies for ReelzChannel in February 2015; his final review was for the
Jude Law disaster film
Black Sea. From April 12, 2010, to October 7, 2014, he co-hosted
The Roe & Roeper Show with
Roe Conn on Chicago's
WLS 890 radio station from 2-6 pm CST. He signed off from that morning TV show on October 18, 2017. On February 2, the
Sun-Times released a statement stating that their investigation did find that Roeper purchased over 25,000 fake followers. The paper later reinstated him, though he was required to begin using a new account on which he was explicitly disallowed from buying followers. In November 2025, Roeper provided a voiceover for a Mr. Submarine 50th anniversary ad campaign, reviewing humorously one of the chain's subs as part of a series featuring
Chicago notables.
Film critic In the mid-1990's, Roeper assumed the role of film critic at the
Chicago Sun-Times, initially filling in for
Roger Ebert on film reviews while continuing his general column work. His contributions grew beginning in 1999, as Roeper took on more dedicated film duties, including daily reviews that were nationally syndicated through the newspaper's network. By the early 2000s, Roeper had established himself as a key voice in print film criticism, producing consistent coverage of new releases that reached readers across the United States. After
Gene Siskel of
Siskel & Ebert died on February 20, 1999,
Roger Ebert co-hosted the show with nearly 30 guest critics. After ten appearances on the program, Roeper was offered the opportunity to co-host the popular film review show with Ebert permanently. The series was renamed
Ebert & Roeper and the Movies in 2000. Beginning in August 2006, while his co-host Roger Ebert was recovering from cancer surgery, Roeper was joined by numerous guest critics, including
Clerks director
Kevin Smith,
The Tonight Show host
Jay Leno, and singer-songwriter
John Mellencamp. On Sunday, July 20, 2008, Roeper announced that he was leaving the show in mid-August and would return with a new show later in the year. However, plans for a new program starring Roeper failed to materialize. Between 2009 and late 2010, Roeper contributed video reviews to
Starz. In August 2014, Roeper became first-string film critic for the
Chicago Sun-Times, where he made his debut reviewing
Guardians of the Galaxy. During this time, he expanded daily reviews to include TV and streaming content while maintaining syndication. He is a member of
Chicago Film Critics Association. Since 2021, he has hosted a podcast entitled
The Richard Roeper Show (formerly
Screen Time with Roe and Roeper which he hosted with Roe Conn until 2022) for American Eagle, which airs every Tuesday and Thursday. In 2025, the program evolved to address timely issues, most notably an October 2025 episode dissecting the NBA gambling scandal involving figures like
Jontay Porter and its broader implications of
sports betting integrity. On March 19, 2025, Roeper revealed that he accepted a buyout from the
Sun-Times to terminate his employment, ending his time at the newspaper after a 39-year run. Despite this, he is expected to keep reviewing movies on his podcast and for
Windy City Weekend on
WLS-TV. Roeper's last review for the
Sun-Times, published on March 20, 2025, was for
Snow White. In 2025, Roeper became a regular contributor to
RogerEbert.com. Later that same year in October, he launched the podcast
The Movie of Your Life which explores connections between life experiences and beloved films. The series premiered on October 17, 2025, with a November 3 episode featuring an in-depth discussion with
Chaz Ebert on her preservation of
Roger Ebert's legacy, the evolution of
film criticism, and the influential movies in their lives. ==Critical style==