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These days, fans celebrate Bob Odenkirk for his more serious work in Better Call Saul. But he entered the entertainment industry as an aspiring comedian from the Chicago suburbs. As a young, ambitious man desperate to make his way out of his small town, Odenkirk took on jobs at Saturday Night Live and Second City at the same time to advance his career.

The constant travel was tough on him, but the comedian had no real problems doing it until a robber held him up at gunpoint. Considering Odenkirk’s persona in most of his roles, he wormed his way out of the situation in a way you might not expect.

Bob Odenkirk pulled double duty to make his way as a young comedian

Odenkirk recently appeared on Dax Shepard’s Armchair Expert podcast to discuss his career, family, and new book, Comedy Comedy Comedy Drama: A Memoir. His first comedy job was writing for Saturday Night Live in 1987. Two and a half years into his stint on the sketch comedy show — he eventually left in 1991 — he received a job offer closer to home. 

“I got a phone call from my friend Tom Gianas, who is going to direct the next main stage show at Second City [and he asked], ‘Bob, do you want to be in the next mainstage company?'” Odenkirk agreed to take the gig. Second City is a premier comedy club, comedy theater, and school of improvisation.

At Second City, Odenkirk worked on bits with future stars Chris Farley and Tim Meadows. One character they created, motivational speaker Matt Foley, became a beloved personality on SNL.

Doing both jobs meant committing to an intensive routine full of tight deadlines as Odenkirk flew from New York City to Chicago and back. “The second half of the season at Saturday Night Live, I was flying back to Chicago after read-throughs,” he explained. “So there are three improv sets I would do after their main stage show and we’d write during the day, and then I would fly back to SNL.”  

An attempted robbery interrupted Bob Odenkirk’s Second City/’Saturday Night Live’ routine

Comedian Bob Odenkirk acts in a Saturday Night Live skit in 1990
Bob Odenkirk (C) in a Saturday Night Live skit in 1990 | Raymond Bonar/NBC/NBCU Photo Bank

Odenkirk kept his schedule close to the vest. The only people who knew what he was doing were Robert Smigel and Conan O’Brien, two writers he created an improv comedy show with called the Happy Happy Good Show in 1988 in Chicago. 

Understandbly, Odenkirk wasn’t sleeping much with two jobs and constant travel. Anyone who has experienced sleep deprivation knows it’s hard to focus in that state. However, if anything will snap you back to reality, it’s having a gun pulled on you. 

“I was leaving the show with my girlfriend at the time in Chicago,” Odenkirk told Shepard. “So it’s probably 1 am after the improv set, and I’ve been up since Tuesday morning at 10 am in New York. It’s now Thursday morning at 1 am. Somebody pulls a gun. It looks like a s—-y zip gun … But it’s a gun gun.”

Odenkirk went on to explain that he was so tired that he felt numb while being robbed. His wallet was, in all seriousness, in his other pants. So, he had to convince the robber to let him open the trunk to get his cash, all while his partner freaks out in the front seat. 

“I take out my bag, and I put it on the sidewalk, and I finally get the bag open. And I know I have a lot of money in there — at least $300 cash ’cause I was traveling. I figured I can make him happy.” A nice thought, but the robber decided to go for the whole shebang and demanded his girlfriend’s jewelry as well.

Odenkirk had a surprising way of getting out of the situation

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At this point, most of us would just give up the valuables and move on. But a fatigued Odenkirk reacted in a way that sounds like something out of an alternate version of Nobody. 

“I’m going to credit this not to my bravado or my courage, but to how tired I was,” Odenkirk explained. “I go ‘What the f**k!’ I said, ‘Look how much money you got. Get the f–k out of here! You should go!’ And [the robber] stands there, right by the window of the car, not sure what to do. And I go, ‘Run! Go!’ And he does. He leaves.” 

Odenkirk believed that the assailant didn’t want to escalate the situation and use the gun. Later, a police officer told him that if anyone pulls a gun on you, it’s safe to assume they are willing to use it.

Odenkirk ended his anecdote with a good piece of advice: “You should always give merchandise or money and get the f–k out of there.”