Sit Down with Richard Roeper

Chicago native Richard Roeper has always known he was destined to write. While growing up in the south suburb of Dolton and attending Thornridge High School, he quickly learned math and science weren’t for him and writing would be his future.

Now 54, Roeper’s writing has made him a well-respected film critic and news reporter and he is interviewed by celebrities like Conan O’Brien and Jimmy Fallon. Roeper is also known for working with Pulitzer Prize winning critic Roger Ebert on the popular television show At the Movies.

Below is the condensed version of an interview I conducted with Roeper.

Did you know right away that you wanted to be a journalist?

I loved to read and write growing up, so yeah I wanted to be a writer of some kind for sure.   I was a huge fan of radio/TV, but wasn’t really sure if I was going to really do that.

That seemed more like a pipe dream to me.

Were you working right away in college?

When I was a senior I was submitting ideas to the Sun-Times and I would just write to them and say “I’m a freelance writer and I’ve got an idea for a story.” I actually had a couple of stories printed while I was still in school, and then when I got out of school I got a features article at the Sun-Times.

So right out of school pretty much I did a couple of odd jobs here and there, but I was trying to make it as a freelance writer. The Sun-Times hired me as what they call an “editorial assistant,” which is really just a glorified way of saying you’re going to answer the phones and get lunch; get your foot in the door.

How did you find your way into entertainment?

I was always into pop culture. I mean, I’m still into hard news to this day, but I was always more into pop culture, music, TV, especially movies. So I started gravitating toward the features department more, getting to know the editors there.

To this day they do this thing where they send a bunch of reporters from all over the country to go to LA or New York and interview the stars of the Divergent movies or whatever, so I started doing that.

So what is your process when you’re writing?

I’ll go to the screening, a seven o’clock screening usually, say the movie ends around nine, I usually drive straight home and fire up the computer and write my review while the movie is fresh. I usually dive right into it.

What direction do you see your future going in your career?

Well I’m still doing radio and I’m still doing TV. I just think it’s more about using the technology and acknowledging it. I love sites like Funny or Die and that kind of stuff.

Can you tell me a little bit about your relationship with Roger?

When I started at the Sun-Times, Roger was already a Pulitzer Prize winning film critic and kind of a legend in the newsroom. Talk about a guy who was really ahead of his time with technology! I didn’t get to know him really well until I was there for a few years; he never wanted there to be a second film critic, not because he was threatened by it but more like he thought it would make him too complacent, but he was really cool about my stuff.

Did he influence who you are as a writer?

Roger, he was a great writer, but he wasn’t a pretentious writer. He’s as smart as anyone you’d ever know. He could have peppered his film reviews with references to the German masters, like silent films and all that, and he knew he was writing for someone who was picking up the Sun-Times on their way to the train or the bus. So he wasn’t dumbing it down, he just wrote it in a way that you’d talk.