The Most Legendary Moments in Second City History

Courtesy of The Second City (edited)
Courtesy of The Second City (edited)

Since opening its doors in 1959, The Second City has served as a comic incubator for everyone from Jim Belushi and Bill Murray to Steve Carell and Stephen Colbert. While the theater is well known for its on-stage hilarity, some of its iconic moments have taken place off stage. To compile a definitive listing of the comedy institutions' legendary moments we've tapped the knowledge of Andrew Alexander, Second City CEO/Executive Producer, who's been with the company since 1973, and Mike Thomas, former Chicago Sun-Times features writer and author of The Second City Unscripted to dish out the dirt on Second City's history both on and off stage.

Courtesy of The Second City

Bill Murray bounces a heckler then finishes his set

One night during a show in Toronto in 1974, Bill Murray decided he’d had enough of an annoying heckler who was tipsy and yelling at him throughout the show. The patron was told to shut up repeatedly but kept interrupting the show until suddenly Murray declared, “Ladies and gentlemen, there’s someone who’s been interrupting the show all night, but he won’t do it any longer!” He then jumped off stage, grabbed the guy, tackled him, and took him out into the alley, beat the hell out of him, and reportedly broke the heckler’s arm twisting it [Source: Mert Rich, The Second City Unscripted]. Then, according to Alexander, “Billy came back and continued the show.”

“Back in those days we were so desperate for an audience," says Alexander, “there was a beer hall right across the street from Second City in Toronto, and people were standing out in line waiting to get into this beer hall. And I’d say, ‘I’ll give you a round for free if you come over to our place.’ They weren’t necessarily coming to see the show. We were just trying to find an audience, and in Toronto we weren’t that well known, we were trying every trick in the book just to get warm bodies in there. Some of those warm bodies were warmer than we would have liked.”

Courtesy of The Second City

Adam McKay makes Steve Carell cry

The Second City Touring Company was booked to play a month-long run at a theater in Dallas, where the owner specifically asked for a show that was "edgy." They probably should have known there were going to be problems after learning the show following them was Love Letters featuring Charlton Heston and his wife. The audience hated them, but that didn’t stop the cast from doing some ‘improvisational experimentation.’ The cast included Adam McKay and Nancy Walls, who was then dating an unknown actor from Chicago named Steve Carell. When he came down to visit Walls during the run, Carell and McKay cooked up the idea that they would pick Carell from the audience as if he were just another audience member. When he got on stage, McKay would then ridicule Carell until he started sobbing. So they ran the bit, but they didn’t really think about how to wrap it up. So the audience was just stunned and then angry at Adam for being so cruel.

Courtesy of The Second City

Bill Murray gets arrested for pot at O’Hare, Second City bails him out

Who would you call if you were busted with FIVE bricks of marijuana? For Bill Murray, there was only one logical choice. As the story goes, on September 21st, 1970 (on Murray’s 20th birthday) he made an ill-advised joke about a bomb while waiting to board a plane to Denver, and federal agents were summoned. While they didn’t find a bomb, they did find 10lb (yes, pounds) of marijuana valued at $20,000, or about $117,000 today. He was arrested and taken to jail, where he called Bernie Sahlins, co-founder/owner of Second City at the time, to bail him out. Murray was eventually sentenced to probation.

Courtesy of The Second City

Poop rains down on the cast at Second City Toronto

In the '70s, Second City Toronto was in financial straits, cast members would make $145 a week and had to rush to the bank to see who could cash their checks first before the money in the struggling theater's account ran out. Dave Thomas (you may know as Doug McKenzie from Strange Brew) was backstage during a performance when, in the middle of a show, a pipe burst above their heads and rained sewage all over their hair and costumes. Alexander rushed backstage to apologize, saying, “One day you’ll look back on these days as the best days of your life.” Amazingly, Thomas seems to agree. [Source: Dave Thomas, The Second City Unscripted]

Courtesy of The Second City

Chris Farley on shrooms pretends to be a seal on icy Lake Michigan

One night, at the suggestion of improv guru Del Close, the 1989 cast, which included Chris Farley, all decided to take mushrooms as a bonding exercise at one of the cast members’ summer homes in Michigan. They went down to the beach, and all assumed hastily invented characters with Farley taking on the role of the “whale boy,” shirtless and diving around on sheets of ice on Lake Michigan. “This is razor-sharp ice, and he’s just diving on it, pretending to be a seal or a whale,” recalls cast member Joel Murray. “And we just laughed our butts off that night.” [Source: Joel Murray, The Second City Unscripted]

Courtesy of The Second City

John Belushi gets out of a drug bust by name-dropping Second City

Before his breakout on SNL, John Belushi was a beloved cast member of Second City Chicago. He was friends with everyone; however, Belushi’s friendship with an unsavory local character named “Dr. Psychedelic” took a most unfortunate turn when Belushi found himself in handcuffs on Dr. Psychedelic’s couch in the midst of a drug bust. Cast member Tino Insana swung by the place to pick John up to go home for Thanksgiving, and when he walked in, Belushi -- who was apparently pleading his case to police at the time -- said to the arresting officer, “He’s in Second City, too!” So the cop took off the cuffs and let them both leave. Then, according to Insana, they ran out of the place “like something out of Animal House.” [Source: Tino Insana, The Second City Unscripted]

Courtesy of The Second City

John Candy walks around an LA party with Chevy Chase in a headlock

In the summer of 1977, Alexander rented a house for the cast to work out of in Los Angeles, where Harold Ramis was a head writer on Animal House. Not only did the cast party there, some of them (including John Candy and Catherine O’Hara) even lived there for the summer. According to Alexander, “It became a bit of a party house.” Candy, who was the big party guy, threw a giant bash where Steven Spielberg showed up alongside Bill Murray, Chevy Chase, and a whole generation of up-and-coming comics. In true Second City form, Candy had Chase in a headlock for two hours walking around the house as if nothing was out of the ordinary.

Courtesy of The Second City

The cast does a show for two people

Back in the ‘70s, Wednesday nights were not a popular night at Second City. One particular Wednesday night, the cast looked out and saw a grand total of two people out in the audience. George Wendt went out to talk to them, planning to inform them that there would be no show that night and he would buy them lunch instead. But Wendt got to talking to them and found out it was their 25th wedding anniversary and that they drove all the way down from Wisconsin, got a sitter, and had to be home by seven. Wendt and cast member Tim Kazurinsky couldn’t say no to such a sweet story, so in a 500-seat theatre, they did a show for two people. According to Kazurinsky, “It was one of the best shows we ever did.” [Source: Tim Kazurinsky, The Second City Unscripted]

Courtesy of The Second City

John Belushi and Dan Aykroyd open a private bar across the street from Second City

When they were in town filming Blues Brothers in the summer of 1979, John Belushi and Dan Aykroyd opened a private bar called Blues Bar across the street from Second City for cast members to hang out and socialize. They had bouncers at the door, and cast members would run over and say they were with Second City, practically begging to be let in to hang with the Blues Brothers and company. At the bar, The Blues Brothers jammed with The Eagles, and the cast would party there until dawn four or five nights a week. Aykroyd called it “one of the greatest summers of my life." [Source: Dan Aykroyd, The Second City Unscripted]

Courtesy of The Second City

Jim Belushi does whippets on stage

If you don’t know what whippets are, first off, congratulations; second, it's when you suck the gas out of whipped cream can to get an intense high lasting about a minute, brain cells be damned. In the early ‘80s whippets were becoming a thing around Second City, and one night Jim Belushi and cast member Danny Breen took their whipped cream cans on stage and attempted to do an improvised bit with the audience after inhaling the nitrous oxide from the cans. In the end, all they could do was laugh at each other. The audience booed. Belushi and Breen didn’t care, they thought it was hilarious. [Source: Danny Breen, The Second City Unscripted]

Courtesy of The Second City

Stephen Colbert locks himself in a bathroom after “blowing it” on stage

In Stephen Colbert's early days at Second City in the '90's, the Late Show host was determined not to laugh on stage come hell or high water. One night while the cast was performing a scene that may or may not have involved false teeth, Colbert lost it on stage and started cracking up -- but the laughter soon turned to anger. “I was so mad that we finished the song and then I fucking blew offstage and went and locked myself in the bathroom like a teenage girl,” says Colbert. “And banged my head against the wall with rage.” [Source: Stephen Colbert, The Second City Unscripted]


Bill Murray steals an Indian rug from a college president

When Bill Murray was with The Second City Touring Company, the cast got booked to play at St. Mary’s College in Indiana. The show went great, and the cast was invited back to the school president’s home for a private reception. Later that night, halfway home on the drive from South Bend to Chicago, Second City producer Joyce Sloane sensed something was wrong. She pulled over the van and saw that Bill had stolen an Indian rug from the president’s home and was holding it through the window on top of the van. She turned around and made Bill return the rug and apologize to the president of the college.

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A former features writer for the Chicago Sun-Times, Mike Thomas is also the author of You Might Remember Me: The Life and Times of Phil Hartman. More details are at

Jay Gentile is a Thrillist contributor and he totally wants to do whippets with Jim Belushi, if any are left. Follow @innerviewmag