I think the "I'm a PC" series of ads was his origin moment - that he fell into those, despite not being an actor or looking for TV work- though I'm pretty sure there's a deeper, more complicated story. (No one builds an entire career by accident.) That led to his work as a correspondent on The Daily Show, somehow - both of which grew out of his prior work at a literary agency, where he was avoiding doing actual writing - and then other TV gigs. [1]
Medallion Status was John Hodgman's book from 2019, specifically the follow-up to Vacationland and the story of "how he's not on TV anymore." (According to IMDB, this may be technically true: he seems to be mostly doing voice work these days, so he's not "saying lines and making faces" at other people on TV shows in recent years. But it seems to be, at the very least, disingenuous.)
The central spine of the book is Hodgman's status level with what he calls "Beloved Airlines." As usual, he presents himself as a self-centered, neurotic type, stuck in his own head and obsessive about the oddest, least useful things. And, as has been true for a lot of similar guys for at least a hundred years, that's a funny schtick - Hodgman does a good version of it, and it works well.
The one caveat I have is that this book seems to use up all of that material, which is non-optimal for someone who wants to sustain a career. But then the meta-point is that Hodgman's career is entirely random and capricious, totally out of his control, because he's not good at any of this stuff anyway.
Medallion has twenty chapters, each one basically a separate story or linked group of stories from Hodgman's being-on-TV life. Being on TV, in this case, includes The Daily Show, though he doesn't talk much about that, as well as his recurring role on the sitcom Bored to Death, what he presents as a bunch of guest roles, and his standup comedy. Hodgman, since he's presenting himself as deeply befuddled and incompetent, doesn't give years or a coherent sequence for any of this - it's just "there was a time I was flying around the country all the time to put my face in front of TV cameras, and now I don't do that anymore, which makes me sad."
The stories are about things like staying at The Hotel in LA - I'm going to guess the Chateau Marmont - his one nude scene, the jobs he had before going on TV, auditions, splurging on vacations with his family out of guilt for spending so much time away from them, and similar things. They're all narrated in that Hodgmanian, unreliable-narrator style, full of arch circumlocutions to avoid saying the names of most things and people (The Hotel, Beloved Airlines, even the names of his family), and the point of most of the stories is that Hodgman is an unlovable, weird man-child who does strange things and got paid what we assume is a lot of money for that for a while, but no longer.
And, again, Hodgman makes all of this quite funny consistently. It's the sad kind of funny, and you hope he doesn't really mean it, but it is funny.
The underlying point, I guess, is that you can fall backwards into a kind of career in public if you have an appealing act - and "John Hodgman" is at least 50% an act by volume - but that craft and hard work and desire need to be part of the mix if you want to continue more than a few years. (Oh, and luck - always, always, a lot of luck.)
So this book is seven years old now, and Hodgman seems to still have a career, however you or he would want to characterize that career. He's not "on TV" the way he was in the late Aughts, and I have no idea if he's touring his comedy, but he's doing voice work at least, I think the recurring writing gigs (Judge John Hodgman and the like) are still going, and probably other stuff. He hasn't had another book since then, for whatever that means.
In sum: if you like the John Hodgman character, this is a big helping of it, fairly pure and well presented.
Two minor notes to close. First, one late chapter is explicitly about the dashed hopes of the 2016 election, which hits much more sourly here in the stupid depths of Trump II than it probably did in the early going of the 2020 election cycle. And, second, Hodgman, that quintessential middle-aged guy, is actually two years younger than me, which makes me feel incredibly old.
[1] Looking at the timeline, an awful lot of that seems to have started in 2006. Again, I find it very hard to believe it was all happenstance or a surprise. Maybe I'm wrong, and it really was a groundswell of casting directors all demanding a John Hodgman type at exactly the same time. But that's not the way the world works, as I understand it. I didn't check all the other activities against the publication date of his first fake-facts book, the publicity tour for which is much more likely to be the instigating moment.
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