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Triumph the Insult Comic Dog, former Gov. Rod Blagojevich and former Cub Ryan Dempster. Credit: Provided; Colin Boyle/Ecoglobalsociety; Creative Commons

WICKER PARK — It's hard to believe the same comic mind is behind “Da Bears,” Triumph the Insult Comic Dog and the animated superhero team of the “Ambiguously Gay Duo.” But all three, and many more, are the creations of Robert Smigel.

Robert Smigel. Credit: Provided

Smigel grew up in New York but moved to Chicago after college, where he became involved in the improv scene with friends like Bob Odenkirk. He left Chicago when he got hired as a writer on “Saturday Night Live” in the mid-'80s, and then became head writer for “Late Night with Conan O'Brien,” where Triumph the Insult Comic Dog was born.

Although he now lives in New Jersey, Smigel said he has only the fondest memories of Chicago, leading to Triumph's upcoming game show on Monday at the Den Theatre in Wicker Park. “Let's Make a Poop,” is in a “Jeopardy”-style format, and will feature prominent locals like former Cub Ryan Dempster, Wieners Circle legend Poochie Jackson and former Illinois governor Rod Blagojevich, hosted by WGN weatherman Paul Konrad.

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“Da Bears” Becomes An Iconic Catchphrase

A longtime sports fan, Smigel said he first found inspiration for “Da Bears” crew, which he calls “my biggest claim to Chicago fame,” not at Soldier Field, but at then-Comiskey Park soon after he moved to Chicago in the early '80s.

“My first week in Chicago, I am a giant sports fan and I went to Wrigley Field
was just thoroughly charmed by the fans and how much cooler they were and how fun were. I was sitting in a pretty nice seat behind the dugout that I was able to get just walking up to the box office. Crazy enough. But then I noticed everybody in the bleachers is having the best time. ‘Right field sucks,' ‘left field sucks,' throwing homerun balls back. I was like, ‘Man, this is cool.'

“Then I went to Comiskey Park to watch a White Sox game. And that's where I really saw a lot of guys with the walrus mustache. You know, the badge of virility? And the aviator shades and it was like a uniform, and then the garish T-shirts with Sox logos on them. And they had kind of a swagger to them. [Dons Da Bears accent] ‘Yeah, it's gonna happen, my friends. No doubt.' And I just loved that misplaced arrogance.”

Smigel said years later, when Chicagoan Joe Montegna was hosting “Saturday Night Live,” Odenkirk suggested that Smigel introduce the “Da Bears” characters (which he had first tried out at a live sketch show). Montegna was host Bill Swerski, along with Superfans Mike Myers, Chris Farley and Smigel, playing Carl Wollarski.

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“It just took off here in Chicago,” Smigel remembered. “[WLUP DJ] Jonathan Brandmeier in particular just kept playing it over and over. And then George Wendt happened to host for the last show that season as Bob Swerski [Bill's brother], where it was all about the Bulls … and then the Bulls won the championship out of nowhere!

“The whole thing just exploded after that. We appeared at the Super Bowl. We went to ring ceremonies for the Bulls. It was crazy. I had more fun with the characters outside of ‘SNL' … It's amazing to me that the catchphrase still exists.”

Triumph The Insult Comic Dog Takes Off

Although Smigel was only in Chicago for a few years, he said his love for the local teams, especially the Cubs and the Bears endures. In fact, when the Cubs finally won the pennant in 2016, instead of attending Game Seven in Cleveland, he instead hung outside Wrigley Field with Triumph, leading fans in chants like “F*ck that goat!” (the source of the Cubs' legendary Billy Goat Curse).

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“I thought to myself, I don't want to be in Cleveland. So I was like, let's just remote with Triumph right outside Wrigley Field. If they win, it's going to be the greatest night ever. If they lose, it's still going to be funny … that remote is just one of my favorite memories.”

Triumph, crafted from a puppet that Smigel and his wife found in a furniture store with an accent he said is based on his Eastern European grandparents, arose out of the “Late Night with Conan O'Brien” team's desire to break apart from the show's predecessor, Smigel said.

“When I started the ‘Conan' show, I wanted it to be different from ‘Letterman'. That's who we were replacing. He'd set such a bar, certain kinds of humor, but it was mostly like found humor, based in reality. He'd have stagehands delivering lines, or he would have the Westminster dogs just run through the aisles of the studio.

“So when I started the ‘Conan' show with Conan and all these great writers, I imposed all these rules. I was the head writer and one of the rules was like, ‘Dogs are going to talk with Russian accents. Any talking bird is going to sound like a parrot.'”

Smigel said he then got the idea for the dog puppet to be an insult comic, a far cry from a Westminster dog. Triumph's first appearance was taking on film critics Gene Siskel and Robert Ebert — another Chicago connection. “This character was able to insult everybody that Conan interviewed. So [O'Brien] would have people on like John Tesh, and he'd be too polite to make fun of them himself. Then Triumph would come out in the third act of the show and tear into John Tesh, and it was cathartic for the audience. [Laughs.]”

Triumph then sat in on Conan interviews with celebrities like “David Hasselhoff, William Shatner, Pauly Shore, anybody that we knew the audience would enjoy seeing. And finally I got to do Don Rickles,” the ultimate insult comic himself. A few years later, Triumph started going out on remotes, to “Star Wars” premieres, concerts, celebrity roasts and of course, Weiners Circle.

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“In Chicago, It's About The Work”

While in Chicago, Smigel lived in Lincoln Park near the performance classes he was taking. He described, “For a New Yorker, it felt so amazing. I would try to explain it to people like, ‘Imagine if Queens was fused with the Village.' So you had all these fun, cool people around. But it wasn't overbearing with skyscrapers like Manhattan. … In Lincoln Park, I still feel like Chicago has this livable quality that I've never found in Manhattan, or in New York in general. And I don't think it's just the geography. I think it's also the attitude of the people. I've talked to friends from the Midwest who just feel like people are more content in the Midwest. In New York, a lot of people move here and they're incredibly ambitious. And there's just this inherent stress I feel sometimes just from being around all these people ‘on the go'.

“[SNL producer] Lorne Michaels, he's very quotable man. And one of his quotes about Chicago was always [Dons perfect Lorne Michaels/Dr. Evil accent] ‘In Chicago, it's about the work.' In Los Angeles, in New York, people making it there are always thinking about what's this going to lead to? In Chicago, people have ambition there, obviously, but they're not in that mindset to the same degree.

“And I gotta be honest with you, before I was hired at ‘SNL', when I got that, there was a little part of me that was like, I wish this happened later. Because I was very content [in Chicago], with the work I was doing. I was in a sketch comedy group, and we were making enough money for me to not have to do any other work. I was living not in a fancy apartment at all; I was sharing an apartment. But I was doing fine. We were making our own shows, and we're changing the show and improvising on Friday nights. It was, in many ways, the happiest time of my life. And part of it was because I didn't feel like, ‘What's this gonna lead to?' I was more like, ‘I could do this forever.'”

Smigel returns to his beloved Chicago as Triumph the Insult Comic Dog on Monday. “Let's Make a Poop” is a one-night-only show — featuring former Cub Ryan Dempster, Wieners Circle's Poochie Jackson and former Illinois Governor Rod Blagojevich, with surprise guests and WGN weatherman Paul Konrad as host — 8 p.m. at the Den Theatre, 1331 N. Milwaukee Ave. Tickets are available here.

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