On a recent wet Saturday evening in New York’s Chelsea neighborhood, a bar full of sweaty, beer-buzzed people were screaming at Tony Hightower. For his part, Hightower—shaved head, microphone in hand, and clad in a black Rosencrantz and Guildenstern Detective Society T-shirt—couldn’t have looked more pleased by the chaos. Both he and the crowd were there for one reason: trivia.
“If you don’t have a drink in your hand, for God’s sake, get one!” he yelled into the microphone, as One Star bar’s flat screens played college football and ’90s alt-rock blared in the background. Then, as he has done at least 2,500 times, Hightower launched into a series of trivia questions—and the pens of a dozen teams began flying across paper.
Hightower is the founder and CEO of Trivia NYC, which has taken the casual quiz night and turned it into an enterprise. The company, which has 40 employees and works out of New York City’s WeWork 27-01 Queens Plaza N, hosts hundreds of trivia nights each week, a range of corporate gigs and bar clients like this one. Attendees range from Jeopardy! champions and geek celebrities (Gilbert Gottfried is a One Star regular) to tourists and locals who happen to wander into a competition. Hightower leaves most of the hosting to his team—he’s too busy figuring out how to run a business he basically invented—but he still hosts on Saturdays, a way to keep his hand in the core of what makes his business work.
The road to Q&A glory was accidental but perhaps inevitable for Hightower. In the 1990s, he was living in Toronto, singing in a band. Looking for its next big move, the band relocated to New York—and then broke up. Hightower took whatever odd jobs he could find. (“I was largely a temp—office jobs, pharmaceutical, legal, whatever I could convince the agencies I was qualified for. I did spend a year as an assistant to David Bowie, which was cool.”) Then in 2006, friends recommended he host a trivia night at Dempsey’s Pub in the East Village. Hightower had two things going for himself: As an avid reader, he had lots of trivia knowledge, and his experience fronting a band prepared him for the crowds: “I was loud and could handle being heckled by drunk people,” he says. The Drunken Smartass Olympics, Trivia NYC’s longest-running event, was born.
Hightower was such a success, requests began to pour in from other bars and for corporate gigs. At the same time, he was achieving quiz glory on the television circuit. In 2008, he snagged $1,400 on the game show Cash Cab. In 2011 he appeared on two episodes of Jeopardy!, winning $23,600. And in 2015 he walked away from Who Wants to Be a Millionaire with $250,000.
Hightower’s trivia reputation was growing, and he began to recruit and train staff to take on the new flow of inquiries. Based on his vast experience, he knew exactly what to look for. “There’s almost no limit to how competitive otherwise mild-mannered people can get,” Hightower says. “If that’s not a thing you learn how to deal with, then you can’t be in this business very long.”
The typical trivia player is extremely driven, he says. “We’re not giving away real estate at these things. We give away books or a round of drinks or something. People have jobs and could buy these things. But they will fight so hard for it, it’s amazing. It’s like Lord of the Flies or something. They just go nuts, and once you figure out how to keep the energy moving, it’s oddly intense.”
Despite the cutthroat side of live quizzing, Hightower sees it as a force for good. He appreciates that it provides an analog way for people to interact who may not otherwise, or learn things about each other that they wouldn’t have if they weren’t trying to compare brains and solve a quiz. “You’re learning something about other people,” he says, “and hopefully yourself.”
And then there’s the ego boost. “You get to show off what you know in front of other people,” he says. “If you’re the only one who knows the first movie to win the best picture Oscar, there’s a rush of superiority that you’ve earned. May not mean anything in term of your retirement plans—but for 15 seconds you think you’re awesome. A little of that is important.” (Wings in 1929, by the way.)
Such was the case with Teresa Candori and Brett Cott, a married couple playing on a team together at One Star on that wet winter night. The couple soared through the first two of five rounds at Hightower’s trivia night with a near-perfect score but were nervous heading into the third round of music questions. “We can get crushed on the music stuff,” Candori said as a song played overhead for a question.
“Is that Lionel Richie?” Candori asked.
“No, it’s Kenny Rogers!” Cott replied. (It was.) They quietly jotted the name down, hoping to best a pack of schoolteachers sitting in the corner who often finish first.
As these rivalries played out, Hightower kept calling out his questions. There was more trivia to come. “I thought I was competitive, but I’m nothing compare to this,” says Hightower. “People let their inhibitions go, and it’s delightful.”