Talking to the 2019 Boston College grad (“I really broke the mold with that one: BC guy moves to Southie. Call me a trailblazer.”) feels like talking to a stand-up comic who happens to be good at trivia. Which is basically his job, he says, as a costumed tour guide on Boston’s Freedom Trail.
The job is “a weird combo of teaching a history class and stand-up comedy. You have to keep people entertained and roll with the punches, because you’ll get people who walk by and heckle: ‘There’s Redcoats afoot!’ I never know what to say to that.”
A three-day winner in December 2022 who won $80,401, McShane is now part of a field of 27 contestants in “Jeopardy!’s” Tournament of Champions, which runs through at least March 14. The first contestant to win three games scores $250,000 and a spot on the upcoming “Jeopardy! Masters” primetime event on ABC.
“Jeopardy!” nerds like me will be tuning in to see how this super-bracket plays out — especially as it’s the first tournament of champs to include a “Celebrity Jeopardy!” winner: actor/comedian/writer Ike Barinholtz plays March 4.
Aside from McShane, two others have New England ties, according to show info: Jake DeArruda, originally from Ludlow, Vt., competed Feb. 28. Brown University sophomore Justin Bolsen — the show’s first-ever “Jeopardy!” High School Reunion Tournament Champion — competes March 5.
I caught up with McShane — who will watch his episode at Southie’s Woody’s L Street Tavern — to talk about his Long Island fiasco, the WBZ video that shocked him, and embracing Southie.
Q. How did you first land on “Jeopardy!”?
A. I have a group of friends; we go to the L Street Tavern to watch “Jeopardy!,” our Monday night ritual. They’d been telling me for months, “You should take the test!” I was like, “I’m going to, I’m going to.” Which is Sean-speak for: I’m not going to.
Then one night [they were pushing] so I took the test. That was January 2022. In September, I got a call: “Hi, Sean, this is Corina from ‘Jeopardy!’” I sat up in my chair. She goes: “Are there any dates in the next two months that wouldn’t work for you?” I was like, “No, no, I’m wide open!” Then she goes: “OK, bye.”
I was like: What was that? Five days later, I get a text: “Can you come out October 24 to tape?” I was freaking out.
Q. How did you find out that you qualified for this tournament?
A. Out of the blue, the week of Thanksgiving, I get an email from a guy at WBZ, the CBS affiliate. He said they’re doing a piece on the Wildcard Tournament and wanted to speak to a past local contestant. I go in. It’s all the stock-standard questions: “Were you nervous?” ”What do you do with the money?” Then at the end, they tell me they actually have a message from “Jeopardy!” They play a video. It’s Ken Jennings. He says, “I’m sorry to tell you we will not be able to invite you back for the Champions Wildcard competition.” I’m like, “OK, this seems kind of mean-spirited.”
Then he goes, “Because you’re going straight to the Tournament of Champions!” My reaction was genuine shock. I never saw it coming.
Q. So you moved here in 2015 to attend Boston College. How long have you lived in Southie?
A. I grew up on Long Island. I moved to Southie in 2019. My first run [on “Jeopardy!”], they introduced me as “originally from West Islip, New York.” I changed it to South Boston partially because, since I was first on, friends who grew up in Southie told me I should say Southie. Which I know could be controversial. It’s like in “Jaws.” “You’re not born here, you’re not an islander.”
I mean it as an homage. It feels like home, a neighborhood in the truest sense. After my first episodes, I’d go to L Street Tavern, or the supermarket, and someone would grab me: “This is the ‘Jeopardy!’ guy!”…
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