Jeremy Cahnmann, founder of Brain Bash Trivia. Credit: Matthew T. Kuehl

LINCOLN PARK – “In the fourth episode of Season 1, what color does Angela say is whorish?”

It’s just another night at work for Jeremy Cahnmann, Chicago’s trivia king. He’s authoritatively spouting off questions about NBC’s “The Office” at Joe’s on Weed Street in Lincoln Park as teams huddle and tentatively answer.

Cahnmann is the 43-year-old founder of Brain Bash Trivia, a company that hosts both television-themed and general trivia events at bars and private parties throughout Chicago.

“The Office” night trivia event is focused on the first three seasons of the irreverent sitcom, and Cahnmann said that the questions he prepared for the competition were more difficult than usual.

Take question No. 23: “In the “Diversity Day episode, which group of people does Michael Scott call ‘explosive’?” Multiple teams incorrectly answered Muslim instead of “Arab.”

“I’m going to make them be precise,” Cahnmann said with a mischievous smile as he grades the pile of score sheets. 

A North Side resident, Cahnmann began his trivia career by filling in for an emcee at Joe’s, about 10 years ago. He was just another host floating from bar to bar, until his cousin Rick suggested he brand himself and start his own trivia company. So Cahnmann, who was already accustomed to making a living out of fun and games — he used to oversee after school programs and kickball and softball leagues for adults through the Chicago Park District — decided to take the plunge.

He never expected Brain Bash Trivia to become so successful, or that he’d receive multiple offers from national trivia companies to buy the company out.

“I thought I’d do trivia for one or two nights a week for a year,” said Cahnmann. “I had no clue that I’d do this full time or that it could be a sustainable business.”

Chicago’s trivia scene has erupted in the last several years. In April, the Chicago Tribune published a list of 100 trivia nights people could go to on any given night. While trivia has historically been a popular pastime — since 1984, “Jeopardy!” has won a record 33 Daytime Emmy Awards and a Peabody Award for encouraging knowledge — Cahnmann credits trivia apps like Trivia Crack and people’s nostalgia for their favorite TV shows with filling bar stools.

At Joe’s, 40-plus teams routinely attend themed trivia nights, and on a dozen occasions so far, more than 100 teams showed up. The first time Cahnmann hosted “Gilmore Girls” trivia, 120 teams packed the space. 

In addition to offering television-themed trivia nights, Cahnmann differentiates himself from other trivia hosts by listening to his participants. After younger contestants complained that they didn’t know the answers to trivia questions geared towards older generations, Cahnmann decided to start offering millennial trivia nights. While he believes there are some things everyone should know, Cahnmann tries to make trivia accessible for those who may not know who Phil Collins is, but can recite the lyrics to Avril Lavigne “Sk8er Boi” by heart.

Jeremy Cahnmann in his element. Credit: Matthew T. Kuehl

Because he’s been doing trivia for so long, Cahnmann struggles to keep his material fresh and challenging — especially for his regulars. He watches hours of television on loop and looks for inspiration in the mundane drudgery of life to create questions. He once got the idea to ask about paint after driving past a Sherwin-Williams.

“My process for coming up with questions is really observing everyday life and what comes with it. If I’m watching something, I’m always thinking, ‘What can I pull out of this?’” he said. “I don’t want the same people coming in thinking they can win just because they’ve come to ‘The Office’ trivia a couple of times before. I want it to be new every time.”

As fun as themed trivia can be, it can also get heated.

“I hate to be that guy,” that guy in a suit interrupts Cahnmann with as he calculates the prize winners. “But just to clarify … that question with Angela and the whorish color. What was the answer?”


“I thought that’s what you said, but online it says orange,” the contestant says, shoving his phone in Cahnmann’s line of vision.

“The answer would be orange if I asked for the ‘Benihana Christmas’ episode, but I asked for ‘The Alliance’ episode.”

“You sly dog!”

Mastering trivia is a learning curve. But for those looking to hone their trivia skills, Cahnmann offers the following advice to instantly improve: “R.T.F.Q.: Read the f—–ng question.”

“Often times people mess up with because they’re answering the wrong question,” he said. “Also if you have nothing else, but your answer’s in the ballpark, give it a shot. People are so afraid of being wrong. But they know more than they think they do; they just have to access that information.”

Blanca Montoya,  the sales manager at Woodie’s Flat in Old Town, said her bar sticks with Cahnmann for trivia because he always brings a crowd and doesn’t need any hand-holding from busy bar staff.

Woodie’s is part of Big Onion Tavern Group, which also runs Fatpour, Derby and other bars throughout the city. 

“Company wide we’ve been using Brain Bash for a few years,” Montoya said. “We use them at all our bars, for all our trivia nights. Jeremy is amazing to work with and has a great crew behind him. They have a very loyal following in the city so I can safely say, if I do an event with them it will always be successful with minimal effort on my part.” 

While Cahnmann appreciates the love, he said he’s glad there are other people running trivia nights in the city — because he likes to play, too. 

“I don’t try to poach other customers and if I can’t handle a bar or I have another bar in the same area on the same night, I’ll recommend other companies depending on what they want,” he said. “I like to go out and play trivia too so I’m glad there’s other companies out there.”

Keep up with Brain Bash trivia nights by following their Facebook page here.