Ryan Long, a Philly Uber driver, just keeps winning on ‘Jeopardy!’

Jeopardy!’s reigning champion might seem familiar if you’ve taken an Uber or Lyft in Philadelphia recently.

Ryan Long, a 39-year-old rideshare driver, continued his winning streak on Jeopardy! Thursday, bringing his five-game winnings to $105,801. His fifth win also qualified him for the show’s annual Tournament of Champions, and is the longest streak since Canadian tutor Mattea Roach popped off 23 victories before losing earlier this month by just $1.

“It’s been really surreal,” Long said of his success. “It didn’t feel real until I saw myself on television, and I was like, ‘OK, so this is a thing that happened and it wasn’t a fever dream.’”

Long is an easygoing guy with a demeanor that hides some of the struggles he’s overcome. He was born in Philadelphia but moved to Bensalem with his parents when he was nine years old. They ultimately separated when he was 13, but his father died before the start of his senior year, forcing him to move back to the city and live with his mom. He said he “barely” graduated from George Washington High School.

“I was probably not the most conscientious student,” Long said. “I was distracted by other things. ... I didn’t go to college right away, I went to work.”

In January 2021, Long was hospitalized for several weeks after contracting COVID-19. When he was released, he returned to his job as a paratransit driver for SEPTA’s Customized Community Transportation program, but quickly realized he was no longer physically able to perform the work.

He eventually turned to driving for various rideshare services to keep the lights on and provide for his 8-year-old son, Nathan. So when Jeopardy! called in February asking if he wanted to be on the program — 16 months after he passed the show’s initial test — it couldn’t have been at a more welcome time. Especially now that he’s in line to take home at least six figures in winnings.

“If this opportunity hadn’t come up, I don’t know what I was going to do long-term,” Long said.

Still, after living paycheck-to-paycheck for more than a year, Long needed some help to afford the plane ticket to California. He also only packed two dress shirts, because that’s all he could afford. He said the show’s wardrobe department has helped him stretch out his look as his continued success kept him on the show.

And if you’re among those who noticed him squinting on the show, there’s a simple explanation — he left his glasses back home in Philadelphia.

“There was a video clue category on Swedish history, and there was a photo of a king with his sword. ... I could not see what that clue was. I just took my best guess, and of course it was wildly wrong,” Long said. “When you watch it on TV, the clue is blown up big and everything, but when you get there the video clue screen is way across the stage, and it’s not that big. So if you don’t have good vision, then good luck to you, pal. You’re going to be struggling.”

When Long arrived at Jeopardy!’s studios in Burbank, Calif., he initially felt he was at a disadvantage because other contestants had flash cards or were discussing their strategy. Some even talked about reading a book about buzzer-beating techniques.

“I didn’t study or anything. I probably should have perused something, but I just didn’t,” Long said. “I just kind of went in and did my thing.”

His willingness to trust his own gut certainly paid off. Long hasn’t been afraid to make big bets on Daily Doubles, including two game-changing bets of $8,000 each. He won both. It wasn’t a strategy — just a feel of where the game was going at those particular moments.

Lengthy winning streaks have become more common on Jeopardy! in recent years. Since 2003, when the show removed a rule that limited a contestant to five consecutive wins, 13 contestants have had winning streaks of 10 or more games. Seven of those have occurred in the last five years.

Four contestants have amassed streaks longer than 10 wins in this season alone. Matt Amodio started the season by adding 20 wins to a streak that would ultimately end at 38 games, the second most in the show’s history — until it was topped by Amy Schneider’s 40-game streak. Roach’s 23-game streak was preceded by Jonathan Fisher’s 11 straight wins.

Regardless how long his current run continues, Long is looking forward to meeting Amodio and Schneider during the yet-to-be-scheduled Tournament of Champions. But for now, he said his Jeopardy! experience is so fresh, he’s not thinking much about the bright lights or the studio wardrobe.

“I want to take my kid fishing,” Long said. “That’s really where my head is at.”