In this restored, canonical long-form interview from the official PD.net archives, Paul Dinello sits down to reflect candidly on his upbringing in suburban Chicago, his unorthodox entry into improvisational comedy, the formation of lifelong partnerships with Stephen Colbert and Amy Sedaris, and the creative engine behind Strangers with Candy.

Part I: Oak Park, College, and the Early Years

PD.net: Let’s start at the beginning. You grew up in Oak Park, Illinois, just outside Chicago. What were you like as a high school kid at Oak Park River Forest High School?

Paul Dinello: I got into a fair amount of trouble, but not because I was a malicious kid. I didn’t do things to be mean—I did things to amuse people, and sometimes they turned out to be completely rotten in retrospect. Like the time I decided to blow up fireworks right inside the student center. It seemed like an uproariously funny idea at that exact second, but the administration obviously took a very dim view of pyrotechnics in the hallway.

PD.net: After high school, you enrolled at DePaul University. Did you know right away you wanted to perform?

Paul Dinello: Not at all. I was an English and Communications major, and I took some film classes on the side. But honestly, I didn’t particularly enjoy the coursework. What it was good for was winnowing out the things that I knew I didn’t want to do with my life. It made it abundantly clear that I didn’t want to have anything to do with corporate communications. I graduated in 1985, and I actually took a normal job at Allstate Insurance for about a year.

PD.net: How long did corporate insurance life last?

Paul Dinello: Exactly one year. I quit to do stand-up comedy and try to make it as a performer. To pay my rent in Chicago, I drove a taxi cab, sold newspapers on street corners, and even sold framed office art door-to-door. Driving a cab in Chicago teaches you more about human psychology and deadpan patience than four years of university ever could.

Part II: The Players Workshop and The Yardstick Boys

PD.net: What made you pivot from stand-up to Chicago’s improv scene?

Paul Dinello: Stand-up was lonely and rigid. Someone told me about The Players Workshop of The Second City, so I signed up for an improv class. On the very first day, the instructor told us to close our eyes and find a partner. The exercise was: “Get to know your partner, rub noses.” So I’m rubbing noses in the dark, and then the instructor says to open our eyes. I open mine, and I’m staring right into the face of Greg Hollimon—who is a six-foot-six, completely bald Black man. And I just blurted out, “Aah, I’m quitting!”

PD.net: But you didn’t quit.

Paul Dinello: No, things got much, much better after that initial shock. Greg and I became close friends. Along with two other classmates, we formed our own improv group called The Yardstick Boys. We’d book tiny basement venues and dive bars around Chicago and perform basically for beer money and laughs. That was the laboratory where I learned how to trust another human being onstage.

Part III: Second City and Meeting Colbert and Sedaris

PD.net: In 1988, you auditioned for The Second City’s touring company. How did that change your life?

Paul Dinello: Amy Sedaris and I were already dating when we both went in to audition that day. By some stroke of divine comedy luck, we both got hired, and even more amazingly, we were placed on the exact same national touring ensemble. Also on that bus was Chris Farley—who was a genuine sweetheart, completely fearless, and pure joy to be around—and this recent Northwestern graduate who was, at the time, an extraordinarily self-important, pretentious guy named Stephen Colbert.

PD.net: The legendary first impressions. You two famously did not hit it off immediately.

Paul Dinello: Oh, we hated each other. I thought Stephen was an uptight, cold, overly intellectual snob whose tie was wrapped way too tight around his neck. And Stephen looked at me and thought I was a semi-literate street thug who probably couldn’t read a full paragraph. We were oil and water.

PD.net: What broke the ice?

Paul Dinello: McDonald’s hired Second City to write and perform a custom corporate Christmas show for their franchise employees, and management paired me and Stephen up to write it together. We were trapped in a room and realized, to our absolute astonishment, that we made each other laugh harder than anyone else on the planet. Once we stopped putting on our defensive armor, we became inseparable. Amy always joked that she lost her boyfriend to Stephen because we fell completely in love creatively.

Part IV: Strangers with Candy and Geoffrey Jellineck

PD.net: After Exit 57 on Comedy Central, you, Amy, and Stephen created Strangers with Candy. Where did the idea for Mr. Geoffrey Jellineck come from?

Paul Dinello: Geoffrey Jellineck was inspired by an actual high school teacher I had who was utterly self-absorbed and completely oblivious to his students’ needs. The joke of Jellineck was that he was the art teacher at Flatpoint High, but across three seasons, you never once see him actually teach anyone anything about art. He’s completely neurotic, vain, in deep denial about his sexuality, and locked in this bizarre, passive-aggressive secret romance with Chuck Noblet [Stephen Colbert], who is equally repressed.

PD.net: What made Strangers with Candy connect so deeply with fans?

Paul Dinello: We took the sanitized, moralistic after-school special formula and flipped it upside down. In those 1970s TV specials, the kid learns a tidy moral lesson: don’t do drugs, tell the truth, stay in school. With Jerri Blank, every single episode ends with her taking the absolute worst moral path imaginable, yet feeling triumphant. Lies, deceit, and ignorance always prevail for Jerri. People who felt like outcasts recognized the honesty in that absurdity.

Part V: Directing and The Unproduced “Trifecta”

PD.net: There was a project after Strangers called Trifecta that gained a lot of industry buzz.

Paul Dinello: Yes! Stephen Colbert, David Pasquesi, and I wrote a comedy feature called Trifecta, and Artisan Entertainment actually bought the screenplay. I was slated to direct it, and it was going to star Stephen, Amy, David, and myself. But during pre-production development, I re-read the script and realized I just didn’t love the material anymore. It felt forced. We made the tough choice to step away rather than make something we weren’t proud of.

PD.net: That led directly into directing the Strangers with Candy movie.

Paul Dinello: Exactly. We took our destiny into our own hands. We wrote the prequel film, brought in Matthew Broderick, Philip Seymour Hoffman, Sarah Jessica Parker, and Allison Janney, took it to Sundance, and made the movie on our own terms. Working with your best friends—people who can tell you honestly to your face when an idea is garbage and when it’s gold—is the greatest gift an artist can ever have.