It’s the Wednesday evening before the Oscars, and all of the TVs at O’Brien’s Irish Pub in Santa Monica have been tuned to ABC. The bar is screening the first night of the new Jeopardy! All-Stars Tournament. Onscreen Brad Rutter—the show’s all-time money winner—is engaging in some moderate trash talk with his fellow contestants: a little verbal sparring with Buzzy Cohen, the bespectacled music executive who won the 2017 Tournament of Champions, a little more with Pam Mueller, the redheaded think-tank policy researcher who is not only a former Jeopardy! college champion and an All-Star but my personal game-show idol.

Weirdly, as we are watching Brad, Buzzy, and Pam on TV, the live versions of the trio are also in the unpresuming bar, just a few feet away from me. While I am stuffing French fries into my mouth, Buzzy is introducing his family to Brad and Pam.

This isn’t an isolated incident. Every Wednesday for the last five years, I have been testing my trivia mettle against Brad, Buzzy, Pam, and a host of other “Jeopardy! people” at the O’Brien’s Irish Pub Quiz, which regularly draws some of the most recognizable game-show champions in the world. Buzzy won nine regular games and the Tournament of Champions; Brad has won more than $4,455,000 playing Jeopardy! and has never lost to a human opponent (his sole defeat having been delivered by Watson, the IBM supercomputer).

This also means that I lose on a regular basis.

But I’m OK with it. I’ve earned my stripes among this group of trivia elites. You see, I am a Jeopardy! person: I won on four episodes last December. (Although, four-game winners are in no short supply at O’Brien’s, and by the time you hail the barkeep, chances are you’ll have rubbed elbows with a half-dozen one-and-done champs.) I’m also an alum of two other game shows, Who Wants to Be a Millionaire? and The Chase. Turns out trivia is like any other competitive activity—even if you’re smart, you’ve got to work at it to get good, and eventually you have to go up against people who are smarter than you.

O’Brien’s quiz regulars are the kinds of people who correct the dates on Timeline history cards at your weekly game night. The kinds of people who, when asked what the capital of Sri Lanka is, bypass “Colombo” and respond by explaining that the legislative capital is Sri Jayawardenepura Kotte, a suburb of Colombo, which is only the commercial capital of the country. The kinds of people who know that Scotland isn’t technically a country but rather a somewhat autonomous region (as are Wales, Northern Ireland, and England).

But O’Brien’s wasn’t always this way.

Turns out trivia is like any other competitive activity—even if you’re smart, you’ve got to work at it to get good, and eventually you have to go up against people who are smarter than you.

In the early days the O’Brien’s quiz was a garden-variety pub trivia contest with a regular host and straightforward questions on a plethora of topics. The environment was collegial. Players hopped on and off teams, and newbies could simply drop by and join a table that needed a teammate. Winning was nice, but it wasn’t the point.

All of that changed in January 2006, when a former Jeopardy! champion named Jerome Vered stopped in on a whim. Jerome, a writer and former researcher for the show Win Ben Stein’s Money, was no one-and-doner. He was a Tournament of Champions runner-up as well as a finalist on the 2005 Ultimate Tournament of Champions.

Impressed with the quality of the questions at O’Brien’s, Jerome returned a week later with a few fellow Tournament of Champions vets in tow. Unsurprisingly, they won, and the first O’Brien’s superstar team was born. Several more would follow. Not everyone was thrilled.

“People were resentful of them at first,” says Beth Milnes, a legal assistant who has been playing the quiz since 1999 and once served as its weekly host, “but we were losing our regulars to new jobs and kids. The Jeopardy! people are the reason the quiz survived.”

Today the quiz is thriving, though Beth—who went on to become a Jeopardy! champion herself—no longer hosts every week. Rather, players take turns writing and asking the questions, which lends the contest an entirely different flavor week to week. Some hosts favor accessible, pop culture-heavy topics: Who was the first actor to have two different characters he’s played made into Lego minifigures (1)? Others prefer more obscure subjects that provoke fist-pounding arguments among teammates: Name four of the nine countries that have a subway but no Subway (2).

The quiz also draws its share of out-of-town Jeopardy! contestants for whom a visit to O’Brien’s is a must-do L.A. attraction, right up there with Disneyland and the Getty Center. Thanks to various secret Facebook groups and an annual trivia convention in Las Vegas, they often already know many of the regulars and are eagerly welcomed onto one of the six to 14 teams competing for $150 in prizes. (Unlike most pub trivia contests across L.A., the spoils at O’Brien’s come in the form of cash, not free booze.)

This being Los Angeles, the most glittering night of the year at O’Brien’s is the annual Oscars Quiz. Which brings us back to Brad, Buzzy, Pam, and me with a mouthful of French fries.

The first night of the 2019 Jeopardy! All-Stars Tournament happens to fall on the same night as the 2019 Oscars Quiz, making this Wednesday evening a particularly star-studded affair.

In addition to Brad, Buzzy, and Pam, some two dozen former champs are milling around, including the evening’s host, Inception and Avatar actor Dileep Rao. Dressed nattily in a dark pinstriped suit, Rao sweeps through the room and distributes copies of an oversized handout that looks like a Sweet 16 bracket on steroids. To refer to this handout as expert-level movie trivia is an understatement; what makes it even more difficult is that teams must complete it while simultaneously answering rapid-fire questions that Rao reads over the bar’s PA system: Name the three Los Angeles hotels that have hosted the Academy Awards (3). Who is the only person to win both an Olympic medal and Oscar? (4)

Psychologists call this a “divided attention” task, though the rest of the world usually just calls it multitasking.

Christopher Fowler

Whatever you call it, it’s not easy. On the televised All-Stars series, Brad, Buzzy, and Pam did well enough to qualify for the finals (and Brad and company would go on to win the $1 million first prize). But even they didn’t prevail at the Oscars Quiz. The movie trivia expertise in the pub tonight is too deep. Another team—a haphazard mix of Jeopardy! and non-Jeopardy! people—walk away with a grand prize of $80 and the right to have an MVP of their choosing wear the O’Brien’s fez in the winner’s photo (a tradition whose origin no one can quite remember).

But finishing in the middle feels like an achievement at O’Brien’s. And should you be the only one in the room who knows an answer—which happens more often than you might think—the experience can be downright addictive. There are no endorphins quite like I-knew-something-Brad-Rutter-didn’t endorphins.

As much as we love winning—whether it’s $80 or $1 million—what makes the O’Brien’s pub quiz different from its more conventional contemporaries is the community it has created. Players often get together on weekends to go to a museum or lunch. And in March we all came together in support of the ultimate Jeopardy! person: Alex Trebek. Though most of us have met Alex only once or twice, he’s been a towering figure in our lives for decades. The announcement that he was suffering from stage 4 pancreatic cancer was like a punch in the gut.

And so, a few weeks after Alex announced his diagnosis, all of the Jeopardy! people gathered outside O’Brien’s to record a message of support for the man who has inspired us to learn more about our world. As I huddled in the wind with Brad, Pam, Jerome, Dileep, and the rest of the crew, I realized that these cutthroat know-it-alls are not just friends. They are family—win, lose, or draw.

Answers: 1. Harrison Ford; 2. Algeria, Armenia, Azerbaijan, Belarus, Iran, Kazakhstan, North Korea, Ukraine, Uzbekistan; 3. the Hollywood Roosevelt Hotel, the Ambassador, the Biltmore; 4. Kobe Bryant.

RELATED: What Surprised Me the Most About Being a Jeopardy! Champ

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