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The 12 best Saturday Night Live sketches about Chicago

As much as we love the Blues Brothers, Harry Caray, Bill Swerski and Wayne, they did not top our list of the best SNL skits about Chicago

Written by Brent DiCrescenzo
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Though it is a New York City institution, Saturday Night Live might not exist without Chicago. Local theaters and Chicago comedy troupes like Second City, iO and the Annoyance have been a farm system for Lorne Michaels for four decades. (In fact, a whopping 40 SNL cast members have come from Chicago. We ranked them all.) Our city has proven to be fruitful fodder for sketches as well. Some of the show's most memorable comic creations have been Chicagoans—the Blues Brothers, Wayne Campbell and an absurdly science-obsessed Harry Caray. Here are the 12 greatest skits about Chicago from SNL's first 40 years.

The best Chicago sketches on SNL

12. Chicago Weddings: How to be a Beautiful Bride

March 21, 1992

In an obscure spin-off of the Superfans, local product Beth Cahill plays Denise Swerski, giving make-up tips for South Side brides-to-be. 

11. Weekend Update: Rod Blagojevich

October 9, 2013

Our dopey, crooked politicians are comedic gold. Blago's level of cartoonish villainy, and that wave of hair crashing over his forehead, made him an easy and appropriate target. Jason Sudeikis's impersonation shared our local joke with the nation. "It's like beating a dead whore," he says to Seth Meyers, who notes that is not how the saying goes. "Yeah, not where I come from."

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10. Kickspit Underground Rock Festival

December 5, 2009

As much as we don't want to, Illinois can claim this Insane Clown Posse parody as our own. At the time, the annual Gathering of the Juggalos was held in our state, and the festival released promotional videos that were honestly this absurd. Frankly, much of this could apply to many of our local summer music festivals. Chicago is kind of the capital of going to the bathroom in your pants at a concert.

9. Dyke & Fats

March 29, 2014

The newest entry on our list is a cute jab at the old buddy cop show…until guest host Louis CK shows up at the end as the sarge and the clip suddenly, briefly, turns into a brilliant statement on language. We'd watch the hell out of this show, by the way. Or a movie.

SNL: Dykes & Fats from Justin Cochran on Vimeo.

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8. Daily Affirmation: Michael Jordan

Sept 28, 1991

Michael Jordan is widely known to be competitive. Like, on par with emperors of ancient civilizations. Dude knew he was the best, and pushed to extreme levels to be the best. Which is why it's so funny to see Al Franken push him into admitting, "I don't have to dribble the ball fast, or throw the ball in the basket."

7. Andy Samberg as Rahm Emanuel

October 2, 2010

"Do I lack even basic social skills? Absolutely." Ah, so good to return to this before an election. In another Rahm impersonation, Samberg tells Sarah Palin, "Go back to the tundra, you gimmick." It's hilarious. But something about "Are you ready to choke a man over his vote?" seems so timely.

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6. The Blues Brothers

November 18, 1978

The Blues Brothers are not that funny, nor are they supposed to be. Jake Blues is not a Belushi character like Samurai Futaba. As with his Joe Cocker homage, Belushi, a guy from the West Side of Chicago, was paying tribute to the music he loved. It's charm amplified to levels of humor.

Blues Brothers- Soul Man (SNL) from Cole Williams on Vimeo.

5. Bill Swerski's Superfans

January 12, 1991

If you don't think people in Chicago really talk like this, I've known a few Metra train conductors who will convince you otherwise, with their hissing sibilants and blue-collar drawl. "Da Bears" routine grew tiring fast—and people still do it—but the skits offer subtle humor, like Mike Myers's matter-of-fact Bulls prediction.

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4. The Olympia Restaurant

January 28, 1978

Would the Billy Goat be around if not for this skit? Lorne Michaels should get a penny off every cheezborger they flip. What's so great about this, and so different from how the show operates now, is that it feels like a short film, shot live. The panic on Bill Murray's face is priceless.

3. Wayne's World

Dec 1, 1989

Aurora seems like the perfect home for Wayne and Garth—a fading suburban setting that makes you feel like you're going nowhere, but close enough to a massive city to let you think you're in the big time. Hanging out at Stan Mikita's Donuts, an analogue to Tim Horton's we so wished existed, and wearing Blackhawks jerseys, these two burnouts helped make working-class Chicagoland cool.

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2. Harry Caray: Space, the Infinite Frontier

May 17, 1997

"It's a simple question, doctor. Would you eat the moon if it were made of ribs?" Try to find a funnier line than that in the history of SNL. 

1. Matt Foley, Motivational Speaker

May 8, 1993

You might not realize this, but that van was down by a local river, perhaps the Chicago or the Fox. The Matt Foley character was named after a priest in Little Village and developed on the Second City stage by Farley and Bob Odenkirk, who brought the wrecking ball to NBC. That fall in the original skit below was an accident, but it soon became Farley's shtick. In a later sketch, Matt Foley heads to Joliet Prison to scare some prisoners straight, proving that, yes, he is a local. Hooray! We really wanted to claim this one.

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