As you may have seen, Lawrence “Skip” Long of East Bend, North Carolina has become an instant legend thanks to the following things:

I wrote about all of this in this week’s free newsletter. But! I’m lucky enough to know Claire McNear, a reporter with The Ringer who wrote what I consider to be the definitive Jeopardy! book, and also broke a story that led to the eventual resignation of new host-in-waiting Mike Richards. She knows the show, its producers, its mechanisms, and its contestants like few do. So, I asked her to explain how Skip Long was able to make the most of his time on a show that leaves very little room to show personality.

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Jeremy: Explain the format of the show. It feels like the only spot dedicated to personality is right after the first commercial break.

Claire McNear: Yep, and that's by design. Each episode of Jeopardy! features just 22 minutes of the actual show—which is not a lot of time to squeeze in the 60 total clues of the Jeopardy! and Double Jeopardy! rounds, plus Final Jeopardy! and its doo-doo-doo-doo-doo-doo... deliberation tune. So the only time we get with the contestants that isn't watching them play is when they wave (stare, shellshocked) at the camera during their introductions, and then whatever chitchat they get in with the host after the first commercial break.JM: Everyone prepares really hard to be a Jeopardy! contestant, it seems. How hard do some contestants prepare for their chit-chat with the host? How scripted or rehearsed is it?

CM: This is something that contestants have a tendency to obsess over. If you get chosen to be on Jeopardy! (and that's hard to do; only about 400 people get the nod out of the approximately 125,000 hopefuls who apply each season) the odds are pretty good that you can hold your own with trivia. That doesn't mean that people don't spend weeks and months drilling themselves on Canadian geography and famous impressionists, but broadly speaking, they probably know what they're doing most of the time.

The chitchat segment is totally other. Contestants are acutely aware of this being their one moment to show another side of themselves on national television, which can be nerve-wracking. I've talked to more than a few who have dramatically embellished or outright made up their stories. Generally, the way it works is that before they play, each contestant has to write down a handful of personal anecdotes that might work. The contestant minders then look through those, identify the ones they think are strongest, and usually ask the contestants to do what's essentially a run-through bit of banter with them to see how it might go onstage with the host.

Weirdly, the onstage chitchat segment is the one moment that contestants get to talk directly with the host: Because the host has been staring at the answer sheet all day, they're not actually allowed to talk to players off camera, lest any shadiness go down. (See: Quiz Bowl, which is about the 1950s game show scandals that led to this policy.) In the Trebek era, a lot of players would memorize their opening line—I have collected ceramic caterpillars since I was seven!—and decide in advance that no matter what Trebek said in response, they would reply, "That's right, Alex!" But this could go sideways. The contestant minders would prep notecards for Trebek with all the players' anecdotes and whatever they thought was the best one highlighted. But Trebek would sometimes go rogue and choose whichever one he wanted to talk about on the spot. (So yeah, he really was making fun of people sometimes.) Contestants were often as excited to meet him as they were to actually go on Jeopardy!, so let's just say that nerves could become a factor here.

JM: Unusual occupations are commonplace in, like, the second line of a contestant's chyron on The Bachelor. But the jobs usually listed on Jeopardy! seem fairly vanilla. How, then, did something like "Stay-at-Home Uncle" get through?

CM: Austin Rogers, who won 12 games in 2017, became a fan favorite right off the bat in large part due to his willingness to be a lot zanier than your average Jeopardy! contestant. He's talked about how he thinks that part of the reason he actually got on the show was that he was (and is) a bartender and was introduced as such. Previously, he'd worked in marketing, and he's said that he thinks breaking through—with fans, but maybe also with the casting department in the first place—was much easier as a bartender instead of as someone with a more "boring" (or at least traditional in a Jeopardy! sense) job. We see a lot of stay-at-home parents on the show. I'm not sure we've ever seen a stay-at-home aunt or uncle, but presumably that is indeed what he does.JM: It seems like there's no shortage of qualified contestants out there. Do producers pick some contestants based on interesting backstories? Like, maybe, being a stay-at-home uncle?

CM: Absolutely. Like I said, it's really hard to get on Jeopardy!—even if you're an absolutely brilliant trivia whiz, the odds are just so steep. What's interesting about Jeopardy!, though, is that with so many people (with love: nerds) to choose from, the show doesn't just look for the smartest people it can find. That's certainly a big factor, but it's not the single decisive factor. At its core, Jeopardy! is a TV show, and the folks upstairs want it to be entertaining. They know, too, that a lot of the fun of watching Jeopardy! is this idea that anyone might be able to hack it onstage, from your ex-disco queen on down. So, yeah, I'd say they're acutely aware that having an affable everyman come play—especially one who is clearly very good at trivia—is something people want to see.

JM: Jeopardy! seems like a show that's really built on its format. How hard is it for a contestant to become memorable, beyond the ones who go on to have record-setting (or near record-setting) streaks?

CM: I first started writing about Jeopardy! about five years ago, and the things I would write about were usually these funky viral moments that break through in some sort of bigger pop culture sense. This actually happens a lot on Jeopardy!, whether it's an especially interesting or entertaining contestant, or a bunch of dorks not knowing anything about football, or a game going disastrously for everyone. Part of what's behind that is that the show's audience is so massive—it really is one of these last monoculture holdouts. But part of it is that the show is really built around this ironclad, 61-clue, unchanged-for-decade-after-decade-after-decade format. When something weird happens, it's fascinating.JM: Do you have any inside info on Skip?

CM: Sadly, my shadowy insider sources are holding out on me with uncle intel. But if he wins his fourth game on Thursday, he's got a very good chance of getting into November's blockbuster Tournament of Champions. Five wins guarantees you a spot, but they've been known to tap fan favorites with less than that.JM: No, come on, do you?

CM: OK, OK—Jeopardy! films five games straight through on each tape day. Contestants generally bring three outfits with them just in case. Which means once they get to four or five games, they're often forced to scrounge around for whatever they can find. Sometimes they mix and match previous getups. Sometimes they borrow from other contestants (even—gulp—ones they've just beaten). In the old days, sometimes they'd even borrow a Trebek tie. So let's just say things might start getting weird with America's dapper uncle.

UPDATE: Skip came in third on Thursday night, thus ending his run. We’re not sad it’s over, we’re happy that it happened.