Pep-pering jokes from YAMO, to SNL, to Boom Chicago

Pep-pering+jokes+from+YAMO%2C+to+SNL%2C+to+Boom+Chicago

When I think of Amsterdam, the first things that come to mind are bikes, canals, art and—I don’t know—tall, skinny buildings? The point is, when I was in Amsterdam back in 2019, I was not thinking about comedy. 

But Pep Rosenfeld was. 

Rosenfeld sees comedy everywhere in everything and was lucky enough (well, talented enough) to make a whole life out of his humor… in Amsterdam of all places.

From ETHS to Northwestern, YAMO to SNL, Rosenfeld found his calling at Boom Chicago; the English-language comedy theater he founded with his best friend, Andrew Moskos, in 1993.

I attended my first improv comedy show at Boom Chicago when I was in Amsterdam, and it left quite the impression. The remarkable uniqueness of the show and the connection the actors formed with the audience stuck with me… but we’ll get to that later. 

To tell Pep’s story, we first need to go back to the 80s, when he was in high school at our very own ETHS. 

“I was on the YAMO governing board. I was the script co-chairman,” Rosenfeld tells me through the Zoom screen (his chosen background is Central Perk from the tv show Friends… just thought I should mention that; a Zoom background says a lot about a person).

YAMO is an entirely student-run, musical-comedy extravaganza that ETHS has been putting on for over sixty years. It’s one of the key aspects of Rosenfeld’s early life that eventually led him down the road of comedy, specifically writing. This is no surprise considering all YAMO has to offer; working with other students that had the same interests and passions as Pep made him realize that maybe he could do this for a living. 

“I think [YAMO] really just put a little message in my head; we can do this, you know, I can do this.

Co-founder of Boom Chicago and long-time best friend of Pep, Andrew Moskos, also has fond memories of their time in YAMO. 

“It shaped me for sure,” he tells me. 

Moskos and Pep met in 3rd grade and “were best friends immediately.” In high school they “hung out every day,” and they’re still best friends to this day. 

“Pep is smart and talented,” Moskos says. “What takes me time and work, he can do seemingly effortlessly.”

Pep didn’t really have a clear idea of his life “plan” until college—well after college, really—but it seems he had the skills to do pretty much anything he wanted. 

Rosenfeld ended up going to Northwestern and majoring in economics and psychology, but that’s not the most important thing that came out of his college experience. 

“There was this show at Northwestern called the Mee-Ow Show. That was it. That was the game-changer.”

Think of the Mee-Ow Show as a more sophisticated YAMO. It offered yet another opportunity for Rosenfeld to experience the magic of comedy, this time with improv. 

Not only did the Mee-Ow Show confirm Rosenfeld’s knack for comedy, it also became the origin of Boom Chicago years later. A considerable amount of the original cast of Boom Chicago came directly from the Mee-Ow Show (including–you guessed it–Moskos).

But it was after college that things really started to come together for Pep. 

When I ask him how he and Moskos came up with the idea for Boom Chicago, he simply tells me, “It was just a dumb idea over drinks!” 

He and Moskos were doing the “classic post-grad trip to Europe,” which brought them to Amsterdam first. 

While there, “we had a couple of drinks, and sort of thought to ourselves, hmm, they speak English. It’s a beautiful city. There are a lot of tourists. I’ll bet we could do an English language comedy show here,” Pep recounts.

And that’s exactly what they did. 

“We were in the back of someone’s salsa bar the first summer. But the next year, it was a real theater, and then it just got a little bit bigger every year,” the comedian says. 

Rosenfeld tells me that he didn’t think it would last at first. According to him, it was just going to be a summer project until they realized they could really do it for a living. 

“The mix of hard work and real fun was phenomenal,” says Pep. “It was just unbelievable to do it with such a good friend.”

At this point, I just had to ask; where does the name Boom Chicago come from? 

Rosenfeld laughs and tells me; it’s actually a really funny story. (Of course.) 

“We wanted a name that would mean the same thing in every language, you know? Something’s happening, and it’s coming from Chicago,” he explains “So we thought BOOM would be a great word. Well… it turns out, there’s a Dutch word, spelled b-o-o-m, that means tree,” he says, laughing.

Nevertheless, the name stuck. 

The first few years of Boom Chicago were crucial in the development of the theater and brought in a lot of attention from people in Amsterdam and, really, around the world. 

One of the unique things that earned them that attention, according to Rosenfeld, is that they “really try to make shows that are both really funny and have a point. We don’t like it when things don’t have a point. And we don’t like it when things aren’t funny.” 

This is a more uncommon take on humor that stems from Pep’s interest in news and the “real world.” 

Rosenfeld also explains that they “really like being connected to the audience. I think we’re one of the few theaters that really celebrates that feeling.”

When I was there, I definitely felt this. The actors on stage were able to put on a show that was both hilarious and involved the audience more than any show I’d ever been to before. This effectively created a memorable night that would no doubt draw viewers in for another show. 

Whether Rosenfeld was writing, directing or acting in the shows himself, the experience of creating something so profound with his friends was something that became really important to him throughout his life. 

In fact, this key aspect of his life was put to the test in 2000, when he went to write for SNL. 

“It was crazy exciting. It was fantastic,” he tells me. “My whole job was reading the newspaper and writing jokes about the news. I mean, I was doing that anyway, just for fun, so that was great. It was a fantastic experience, a mind-blowing experience, a really unique experience.”

Rosenfeld really emphasizes how great the experience was; obviously, it’s SNL—the dream of all comedy writers. But at the same time, it seems like he felt that something was missing. 

“There was something phenomenal about being on the floor during the taping of SNL when one of your jokes gets said, it was fantastic,” he tells me, tapping into one of the good things that came out of the experience, “but at the same time, it’s one of those things where you kind of go, oh, it’s not really what I wanted it to be.

Pep tells me that he loved living in New York but always found himself thinking, “Hey, it’s kind of like Amsterdam, but with too many cars!”

And as it turned out, the city wasn’t the only thing he missed. When Moskos called Pep up to congratulate him on SNL, he also promised that if Rosenfeld ever wanted to come back to Boom Chicago, there was a space for him. 

“I was like,” Pep says, reflecting on Moskos’ offer, “that is what I want to do. I love my life in Amsterdam, at Boom Chicago.” 

So, when SNL didn’t renew Pep’s contract after six months, he was not entirely devastated. After all, he realized he had something even better in Amsterdam. 

“I really am proud of the fact that Andrew and I built this place that makes all sorts of people laugh.”

But there’s more to Pep Rosenfeld than just laughs. One of the points that friends of Rosenfeld bring up the most is Pep’s absolute and unblemished kindness. He has a kindness about him that not everybody who is funny has. A lot of people make fun of others as a part of their humor, for example, but Pep was never that way.

“[Funniness] is not just you being mean to someone else, because that doesn’t count. That’s too easy,” Rosenfeld says. 

Pep never shied away from a challenge—creating Boom Chicago, writing for SNL or raising his kids. When I ask Pep what he thinks his biggest accomplishment is he doesn’t say Boom Chicago or even SNL, he says, “If in 10 years, my kids have happy lives, that’ll be my greatest accomplishment. Right? Gosh, what a sappy thing to say, but I really do mean it. If my kids are happy, then it’s all worth it.”

Sappiness aside, it’s important to note that, minutes later, Pep does stop me mid-question to tell me that maybe his biggest accomplishment is actually making Obama laugh. What?!

More important than the laughter of former presidents is the effect that Pep has on those closest to him.

“Pep is smart and talented and, let’s be honest, funnier than me,” Moskos admits. “He makes me laugh.”

So Pep Rosenfeld has had a pretty cool and crazy life, but what’s even more amazing than his many accomplishments is that he didn’t lose himself along the way. Pep Rosenfeld is still that charismatic, kind and hilarious guy that he was when he was in high school: the guy that everyone loves.

“Take all the opportunities you get,” Rosenfeld says, naming his best piece of advice. “Better yet, make your own opportunities. And remember, you’re better off doing something with a trusted friend than you are trying to do it all by yourself.”