You’ve been a Chicago staple for the past 25 years as a trusted author, columnist, film critic and radio host. What aspect of your career are you most proud of?

This right here, I’ve been waiting for A Drink With! You know, I’ve been very blessed. Growing up in the south suburbs I was always a huge fan of WLS Radio, we subscribed to the Chicago Sun-Times and I watched “Siskel and Ebert” so I got all of these jobs at places that I idolized as a kid. I’ve had a lot of great career breaks and great opportunities but I really think the first one and the job that I still love the most is writing the column for the Sun-Times. I started working for the paper when I was 24 years old and I was lucky to get my foot in the door and I’m lucky to still be there. I’ve been writing for the paper now literally half of my life so that to me is what I’m most proud of.

Has there been anything you’ve written and later regretted?

I look back at some of the columns I wrote a long time ago and think, “Okay, my views have changed,” but I try to be as fair as possible. If I’m criticizing someone, I’m criticizing their work. I don’t go after them personally. I try not to take cheap shots about anybody’s looks or their personal life. Now if their personal life becomes the story like Lindsay Lohan, you’re going to write about it but you try not be cruel. Especially now as I’m older writing about younger people I try to be a little more forgiving because, God, if someone was following me around when I was 22 I wouldn’t be here today!

Who are the people you look up to?

One of the great things about Chicago is the rich tradition of journalism. People are really smart and into the news here. You go to L.A. and people don’t really watch the local news that much. In New York they do a little bit more but in Chicago the 10 o’clock news anchors are like superstars in this town. And they should be! We have Ron Magers on our show and I love Ron, he has a million great stories. When I worked at Fox I worked with Bob Sirott, he’s a Cubs fan and such a great Chicagoan, a real talent. He’s also very generous with his time and advice. Those are the kind of people I look up to, people who are secure enough and have done enough that they like helping and mentoring. Roger Ebert was always like that with me.

What is one of your fondest memories from working with Roger Ebert?

The minute I signed on to do the show he was like, “We are equals, we’re partners. It’s gotta be fifty-fifty and you can’t act like a guest on my show.” Our first time on “The Tonight Show” they were like, “Okay, Roger sit next to Jay Leno and Richard will sit on the couch,” and Roger was like, “Next time Richard is going to sit next to Jay and we’ll switch.” You learn from that and I try to be the same way with young producers here or younger writers at the Sun-Times. I never force it on people but if they ask I’m thrilled to help.

Do actors try to get on your good side when they have a film coming out?

Some do! Some are tired of sucking up and some don’t talk to me anymore.

Are there ever times where you still get starstruck?

Yes, I still do but I think it goes back to your place in the world chronologically. When I meet somebody who I looked up to as a kid, I’m still awestruck. I recently had dinner with Robert Redford—I’ll drop that name—at the Sundance Film Festival. So you’re having dinner with Robert Redford but you are also thinking, “I can’t believe I’m having dinner with Robert Redford!” Another time at Sundance someone said, “Al Pacino would love to get a beer with you,” and it didn’t seem real to me because I think of the 12-year-old me watching “The Godfather”. It’s still really cool! The same thing with athletes. We had Dick Allen in here yesterday, he played for the White Sox when I was a kid and going to games all of the time. He’s 70 now but to me he’s still this 30-year-old guy. Meeting people like that who I really looked up to as a kid, that’s when I get starstruck.

You were once named one of People Magazine’s most eligible bachelors. Is bad taste in movies a dating deal breaker for you?

First of all, what I say about that is that I’m also eligible for the NBA draft but that doesn’t mean anyone is ever going to pick me. You know, just to be eligible? Big deal! As far as dating, I’m seeing a great girl now. She’s fantastic and very understanding of my schedule but she’s had to learn what everyone else I’ve already dated had to learn, which is we’ll never go on a movie date because that is the last thing I want to do on the weekend!

Where is a place you can go in the city to just be yourself?

I have a place but I’m not going to tell you where it is! I’ve lived in the city for a long time. I live in River North and it’s a great area because you can walk out of your place and there are a hundred places to go. If I want to go to a restaurant or get a beer even if it’s snowing sideways I can walk outside and just go half a block to be sitting in a warm neighborhood place. I’m not a big foodie, I appreciate good restaurants but I’d rather go to a place like the Kerryman and have a salad and sit outside.

What do you do for fun?

I was [in sports leagues] for years and this is my first year not playing in one because of my schedule. I was playing 16-inch softball and had broken my finger so I was like, “This isn’t good for someone who has to type.” People were like, “You’re a grown ass man and you have a splint on your finger like you’re a 12-year-old in little league!”

Best piece of advice you’ve ever been given?

I think the best piece of advice is to watch and learn from people who have done very well in the business and to observe. See people who have achieved a great deal of success and how hard they still work and how they treat the people around them.

What would you be doing today if you didn’t make it in this industry?

It would be something where I was still expressing myself creatively. It might have been trying to do more on the fictional side of writing like screenplays or stand-up comedy, something where I would still get a chance to express my opinion. If not, I would just be the most annoying guy in the law office.

If you could have a drink with anyone, who would it be?

Now that I’ve had one with you guys? That’s a great question. I mean the obvious would be, how could you not want to sit down with the president? I am so lucky to have met the last four presidents. But who would I sit down with? It would have to be Barack Obama but I would have to be getting the real Barack. Not that he isn’t the real guy but I would want to hear like, “Okay, no one is ever going to know about this.” That would be the best!

Photography by Neal Agustin