Four years ago, an announcement appeared on the Grateful Dead subreddit. “Casting Knowledgeable Deadheads for Pilot of Grateful Dead Game Show Podcast — Prize for Winner,” the message read. “It’s called Guess the Year.” That was followed up three months later with an Uncle Sam-style recruitment poster, featuring a skeleton pointing to the viewer. “We still need contestants!”
These posts were written by host Mike McClure, who launched Guess the Year in October 2022. The podcast is as self-explanatory as it sounds: each episode, several Deadheads join a Zoom call, listen to the first part of a Dead live track, and guess the year it’s from, based on clues like guitar and vocal style, song selection, keyboard playing, and so on. And just like a Final Jeopardy! round, contestants silently submit their answers to McClure via chat. He then reveals the answer, and whoever is furthest off is eliminated.
As McClure wrote on Reddit, Guess the Year is “a very fun combination of intense game show and completely relaxed hang between Heads.” But as he tells Rolling Stone during a Zoom call last spring, he had reservations about it at first. “I was mortified that I was just taking up everyone’s time, just annoying them, basically,” says McClure, 35. “They’d agreed to do this for this random kid, and now they’re just waiting to get off the call. But the moment I realized it was a good idea was when everyone started playing. They seemed to have a good time.”
Guess the Year is indeed a good time — a fascinating look into the minds of Deadheads as they contemplate where a song fits into the band’s 30-year career (strictly within the Grateful Dead catalog, as offshoots like Phil and Friends or Dead & Company are not included). Listen to a single episode and you’ll hear experts from all over the globe debating minute details casual listeners would never think of. Is this “Jack Straw” from January 1978, when Jerry Garcia had laryngitis and couldn’t sing? Is this “Franklin’s Tower” from 1991, given the euphoric keyboard sounds — as one contestant put it — like Vince Welnick winning Mario Kart? What about this crisp “Eyes of the World,” and how it seemingly has just one drummer, which narrows it down to 1971 to 1974, when Mickey Hart was out of the band? Or maybe this “Scarlet Begonias” is from 1977 because it just sounds…absolutely perfect?
Mike McClure at Sunshine Daydream Festival.
Dillon Cameron
Unlike other music expert podcasts, this one is stripped of any mansplaining or ego — picture just a bunch of music lovers in a room, sitting by a fire and going deep on how young Bob Weir’s vocals sounded in 1970. And you don’t need to be a Dead scholar to participate. “People think that I’m auditioning somehow,” McClure says. “If you email me, you will get on the show.” There’s also a guest each episode selecting the songs; past curators include longtime Dead publicist Dennis McNally, Phil Lesh’s sons Grahame and Brian Lesh, and others (including this writer). Guess the Year is such a delight that Chuck Klosterman, famously not a Deadhead, joined the show for an interview.
As a host, McClure is relaxed and lovely, a vibe he says he channels from the late Alex Trebek. He also only offers commentary when necessary. “That’s not a privacy thing,” he says. “It’s just an aesthetic choice. There have been times when people have gone to my same high school or been to the same show I have. And I make a rule. I’m not going to say, ‘Oh, me too!’ because it never goes anywhere.”
And like most podcasts, he has to edit when conversations drift off. “Someone will go on for 20 minutes about their time in the can, listening to the Dead,” he says. “One time there was this old guy who had just gotten out of prison and he was in his kitchen just chain-smoking cigarettes, going on and on. And a lot of it’s entertaining, and a lot of it’s not.” It’s only once they’re eliminated that contestants give a brief exit interview, explaining how they got into the Grateful Dead (we liken it to getting “on the bus”) in the first place. “People can tell everything about their life through that answer,” McClure says.
McClure currently lives in San Rafael, California — fitting for a Deadhead — and was raised in nearby Marin. “I was vaguely aware that in this town, there were two famous people: Sean Penn and Phil Lesh,” he says, noting that he played little league baseball with Lesh’s son, Brian. But despite hailing from the Bay Area, he didn’t grow up listening to the Dead. Instead, he loved 2000s rock revival-era groups like the Strokes and the White Stripes, and even preferred Sublime’s cover of “Scarlet Begonias” over the original.
Posters by Dillon Cameron
He finally got on the bus in July 2015, when he attended the first of the three Fare Thee Well shows at Chicago’s Soldier Field, the band’s 50th anniversary celebration. He remembers hopping the fence with his pals, and realizing a Deadhead was watching them. “I was like, ‘Oh my God, that guy spent a thousand dollars for this show, and he’s going to tattle on us,’” he recalls. “And then he came running back 20 seconds later and he’s like, ‘All good, man! The coast is clear! No security!’”
After attending Indiana University and briefly living in Chicago, McClure moved to L.A. to become a screenwriter and got a job working as an assistant to the U.K. singer and actress Kate Nash. He became obsessed with the cringe classic Nathan For You, Nathan Fielder’s hit Comedy Central series, and began the podcast Assisting, which he admits was an “exact rip-off” of the show.
“I pretended to be an assistant for an actor that didn’t exist,” he says. “I would call businesses around L.A. and try to get him a reservation, like, ‘Well, I’m X’s assistant.’ And they’d be like, ‘Okay, what does that mean?’ It was kind of that joke over and over again: My boss who didn’t exist would give me a task. And then my buddy got a law degree and told me casually one time that it’s really illegal to record people, and that I probably shouldn’t do that.”
During the pandemic, McClure got deeper into the Dead world, and got in the habit of guessing the year of whatever the band’s Sirius XM channel was playing — until he realized that it would make for the perfect podcast. He drew on his screenwriting experience to structure the episodes (“Screenplays are incredibly boring, so you want to keep people entertained until the end,” he says), deciding to eliminate the contestant with the furthest guess each round, and having winners return for as long as their streak lasts. The reigning champion is Steve Urbauer, who won six episodes in a row (and 10 overall, if you count the Tournament of Champion runs). McClure calls him “The Ken Jennings of Guess the Year.”
In 2024, Guess the Year got a shoutout in The New York Times, which led to an increase in followers, including SNL alum Bowen Yang. “He unfollowed me within an hour,” McClure jokes. With a fifth season on the way, Guess the Year is just getting started. But McClure isn’t that worried about its success. “I stopped trying to make it big and just make it so that the people who like it really like it, and I really like it,” he says. “That’s ultimately what matters.”
