A city filled with bars, Milwaukee naturally has no shortage of trivia nights. Most of these know-it-all brawls are run by Quizmaster Trivia and America’s Pub Quiz, among the first trivia companies to launch here almost 20 years ago.
The idea for America’s Pub Quiz came to Michael Landmann in 2007 while playing golf with a trivia-host friend. What started as a hobby project grew into a heavyweight as the company expanded into Madison, Minnesota and even as far as California and Texas.
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Its contemporary, Quizmaster Trivia, similarly exploded out of coincidence. In 2006, British-born Ryan Wickens was a college student and bartender for Shorewood’s now-closed The Brit Inn when “the owner decided we should do a pub quiz, and it fell on me to host,” he says. Leaning on the game’s British roots, Wickens shaped up his own homemade style of humorous trivia that’s now in bars all over town.
How well do you know these Milwaukee titans of trivia? Test your knowledge:
How much cash does the winning team take home in the America’s Pub Quiz statewide tournament?
A: $1,000
America’s Pub Quiz hosts a statewide trivia tournament in Wisconsin three times a year. “As long as you finish in the top 50 teams in Milwaukee, you’ll probably get invited,” Landmann says. To determine who qualifies, they take each team’s top 20 scores for the 16-week season and add them up. The more games you play, the higher your chances. Landmann has seen teams play over 80 times in one season to ensure top scores and entry into the tournament.
How many trivia questions has Wickens written for Quizmaster since 2006?
A: More than 100,000
Wickens estimates that he’s written over 99.9% of the Quizmaster content, much of it rarely recycled. “I have some of my hosts help me with specialty topics where I’m not an expert,” he says. “But because I plan them far enough out, I do my research. I watch the shows. I watch the movies. I have a database that I’ve been saving content in for almost 20 years.”
America’s Pub Quiz and Quizmaster host over 110 local trivia contests a week. Hit up americaspubquiz.com and quizmastertrivia.com to find one.
What specialty trivia topic had Quizmaster’s biggest turnout in 2025, with more than 481 players?
A: Harry Potter
When Quizmaster hosts outdoor trivia at The Landing at Hoyt Park in Tosa, the community really shows up. But it was the Wizarding World last summer that drew the company’s biggest crowd ever. “481 players – and those were just the people I could count,” Wickens says. “It was 84 teams and absolutely nuts, but super fun, and everyone there is a good sport.”
What’s the name of the extra-difficult question category in America’s Pub Quiz?
A: Mission Impossible
This brain-buster has its own cash prize, which grows every week until it’s correctly answered. “I always joke that everyone knows who Attila the Hun is – but can you name his nanny?” Landmann says. It varies by location, but typically the pot starts at $25, with the bar throwing in $5 every week the question goes unanswered. At now-shuttered A.J. O’Brady’s, a Mission Impossible pot once reached $700 after the bar began adding $25 every passing week.
