Fan Favorite Ryan Long Reveals How ‘Jeopardy!’ Helped Him Break Out Of His Shell

When most fans watch Jeopardy!, they assume that the contestants have always been known for their intelligence. How else could one person retain so much information on a wide variety of subjects? While this is true for many contestants, Ryan Long just doesn’t fit this stereotype. In fact, the 16-game winner barely graduated high school!

When Long won his first Jeopardy! game on May 13, he quickly became a fan favorite. Though the quiz show usually attracts professors, graduate students, and attorneys as contestants, Long was introduced as a rideshare driver. Viewers took note and loved the humility he showed every game he won. By the time his 16-game winning streak ended, he became the ninth-longest winning contestant.

From College Dropout To 9th Winningest Champ

In a recent episode of This American Life, Long shared his journey of “trying to coax himself” to admit his intelligence to the world. Growing up in Philadelphia as a “husky” kid with a mixed-race identity, Long wasn’t quick to show his smarts to the world. In fact, Long barely graduated high school. Then after one year of community college, he became a college dropout.

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“I’ll oversleep, or I’ll be late, or won’t show up, something like that,” Long remarked about why things like school are difficult for him. “It happens a lot, especially for things that could potentially benefit me. Because some part of me is either ‘this is stupid’ or ‘you don’t deserve it’ or something. And I’m pretty sure that’s depression.”

For someone who is so reserved and has a difficult time admitting how smart they are, it took a near death experience for Long to even take the Jeopardy! entrance test. After being hospitalized with COVID-19 in January 2021 for three weeks and then being diagnosed with diabetes, Long knew he had to make some changes.

“I felt in the moment like I’d wasted my life thus far,” Long reflected. “I hadn’t done anything I wanted to do. I hadn’t gone anywhere that I wanted to go. I started feeling like maybe I didn’t have a huge amount of time left.”

So the winner took the quiz show’s entrance test, got a call from Jeopardy!, and headed to California thanks to money he received from friends and family. Even though he was invited to audition, Long still thought it was a long shot for him to win.

“These are people that all year long they study, buying books on the buzzer technique and all that,” Long said. “When I’ve found out that people did that…I felt like, oh, should I have studied? I guess, maybe.”

Turns out, there was no need for Long to study. After winning 16 games and $299,400, the college dropout became the eleventh-highest money winner in regular play history. He even spent some of the money on himself, a foreign concept for a man who has always taken care of his family first. Plus, he’s now able to work less, something he never thought possible.

“They say money can’t buy happiness, but it buys everything that makes you happy—even time,” Long wisely said.

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