Over the past couple of months, Wednesday has become one of the busiest nights of the week for Capitol Hill’s St. John’s Bar and Eatery. By 6:30 p.m., the line for the bar stretches to the door.

By 7 o’clock, people have squished themselves into every booth and around every table. The bar recently started bringing its weekend bouncer in on Wednesdays to help with crowd control, co-owner Michael Lee said. 

The buzz builds as the clock ticks closer to 7:30 p.m. Then, illuminated by the glow of the bar’s wall-length dinosaur mural, Leah Caglio clicks on her mic: It’s time for trivia. 

This is Head in the Clouds Trivia, the Seattle-based trivia operation making a name for itself across Capitol Hill and beyond. In Seattle, you can play every other Monday at Optimism Brewing Company, Tuesdays at Hopvine Pub and Wednesdays at St. John’s. 

Head in the Clouds is popular in part because it’s a labor of love. It’s pure fun to play because it’s pure fun to make. And the game comes from an underrepresented source in the trivia world: two queer women.

Caglio and her best friend, Sally Neumann — both trivia whizzes with “Jeopardy!” wins on their résumés — started Head in the Clouds last year during the thick of the pandemic. It was a natural outlet for their lifelong trivia obsession.



Growing up in Phoenix, Caglio would regularly arrive an hour late to tennis practice because “Jeopardy!” aired at 3:30 p.m. (“Clearly, Arizona doesn’t consider it prime-time entertainment,” she said.) Neumann says she would keep score for herself while watching “Jeopardy!” as a kid.

The pair became friends during their senior year at the University of Washington. Soon, they were regulars at weekly trivia nights deep in the bowels of Schultzy’s Bar & Grill on the Ave. They spent the next seven years on the same trivia team at Eastlake Bar & Grill. 

Fast-forward to a world ravaged by COVID-19. Neumann coped with a shutdown Seattle by hosting a monthly trivia series for her friends in the backyard of her Rainier Beach home. Soon after, she and Caglio hatched the plan to turn their love of trivia into a business.  

They started out doing private events, but as pandemic restrictions eased, Head in the Clouds began in-person trivia at Optimism last September, then St. John’s in November, and most recently expanded to Hopvine in April.

The growth feels quick for the grassroots company, especially considering both Caglio and Neumann have day jobs — Caglio is a librarian and Neumann is a therapist. Their trivia’s popularity isn’t surprising, though. There’s something special about Head in the Clouds. 


What’s the big idea?

Head in the Clouds Trivia feels more like “Jeopardy!” than standard pub quizzes, but a version of “Jeopardy!” where the writers have a sense of humor and aren’t 75% male. 

“Trivia has a tendency to make people feel alienated,” Neumann said. “What we’re doing is touching on a lot of things that are smaller parts of knowledge.” 

Think visual riddles about Broadway musicals, and questions on the chemical composition of lipstick or the history of the Canadian tuxedo (coined when Bing Crosby wore denim on denim in Vancouver in 1951).

A big part of making the game more inclusive is expanding who writes the trivia questions. 

“What has become canon in trivia culture basically says what is worth knowing,” Neumann said. 

For the most part, white and male perspectives inform trivia quiz questions and set the standard for what mainstream trivia is. “Jeopardy!,” the gold standard for quizzing, remains overwhelmingly white and male — something Maya Angelou called out in the 1990s. Men are behind well-known pub quizzes across the country such as Geeks Who Drink, King Trivia and Sporcle.


Head in the Clouds feels unique because Caglio and Neumann are smart, funny people writing questions they find interesting. They’re also queer women, a revolutionary demographic in trivia. 

“I don’t know what it is,” Caglio said with a shrug, “but queer people just have better taste.”

Head in the Clouds’ content and construction feels refreshing. The first round is general knowledge, which can either be a potpourri of random questions or a bunch of different questions about one topic, like, for instance, cheese. 

The second round is the “common bond” round, where the answers to different questions relate together by a secret theme. Guessing the common bond earns a team two bonus points. 

Caglio and Neumann write questions with different ways to reach the answer. Usually, there’s an academic and a pop culture route to each solution. During one common bond round, one question was: “What 1996 Muppets movie shared a name with the 1883 Robert Louis Stevenson novel?” 

If a team didn’t know right away, they could work backward from the other answers in the round (Flamingo, Excalibur, New York-New York, Mirage) to find the missing answer: “Treasure Island.” The common bond? Las Vegas casinos.


“We base a lot of rounds on puzzles,” Neumann said. “We do that really intentionally to give people a pool of knowledge to draw from.”

The same strategy can work in the third round, an audio round where either the artist or song relates to an overarching theme. “Waterfalls” by TLC, “Ivy” by Frank Ocean, and “Cry Me a River” by Justin Timberlake appeared on a “bodies of water” audio round, for example. 

When it comes to making up questions, Neumann and Caglio aim to make each other laugh.

Neumann loves the unhinged Photoshops she makes for the fourth round’s visual puzzle. She recently edited Princess Jasmine from “Aladdin” so she wore a basketball jersey to make — any guesses? — “Utah Jazzmine.” 

Recently, Caglio joked with Neumann about doing an “Is It Cake?” visual round, referencing the ridiculous Netflix game show where contestants guess whether an object is real or made of cake. In their version, Head in the Clouds laid out 10 different images of all-white male bands and tasked teams to figure out which was the band Cake. 

“I was quarantined [with COVID-19] and just looking at pictures of Cake and building this deranged ‘Is it Cake?’ round while I had a fever,” Neumann said. 


Neumann said she’s planning a “Who’s your daddy?” visual round for Pride Month, and she and Caglio plan to make all of June’s trivia “super gay.” 

Round five can be any sort of word puzzle, like “rhyme time” (one recent answer: “fallopian tube, Jiffy Lube”) or “before and after,” where teams mash two answers together for a hybrid answer. (E.g., “A model, singer and performance artist with a famous red pout and a soccer team 175 miles from Seattle” was “Amanda LePortland Timbers.”) 

“A kind of cheesy thing we say is we try to work out every part of the brain,” Caglio said.

This strategy tends to scratch at the cobwebby corners of triviagoers’ brains, inspiring fact recall for things people didn’t even realize they remembered. 

The final round also features a consolation prize: The second-place team from the week prior gets to choose the last category. Runner-up categories have included public transit, WWE wrestling and Trader Joe’s. The little bonus keeps teams coming back and inspires Caglio and Neumann to research new and interesting topics. 

“We have so much fun writing and I think that comes through,” Neumann said. “We want to make things off the wall. We get a lot of inspiration from triviagoers.”


A boon for the community

After two years of on-and-off restrictions for indoor gathering, Head in the Clouds has been a blessing for local bars.

Hopvine Pub bartenders told Neumann and Caglio their trivia was the best thing to happen to the bar in five years. St. John’s reaches capacity well before trivia starts every Wednesday, and the bar recently set caps on the number of people per team so more groups can play. They also fixed the outdoor speaker so people can sit on the patio and play trivia, co-owner Lee said.

“Having an event is definitely a clear and tangible sign the world seems to be reopening,” he added. “I wouldn’t call it a sturdy bridge into the future, but like a solid lily pad we’ve landed on.”

If you go

On Capitol Hill in Seattle, you can find Head in the Clouds at Optimism Brewing Company (1158 Broadway) every other Monday, at Hopvine Pub (507 15th Ave. E.) every Tuesday, and at St. John’s Bar and Eatery (719 E. Pike St.) on Wednesdays.

You can book Head in the Clouds for your own event at headinthecloudstrivia.com.