John Hodgman's last book, Vacationland, was a kind of absurdist memoir of a weird kid who'd grown up to the kind of self-aware grownup who really wanted to dig into how he got to where he was, with bone-dry wit and real heart (I compared it to Steve Martin's Cruel Shoes, but for adults who'd outgrown it); in his new book, Medallion Status: True Stories from Secret Rooms, Hodgman offers something much more uncomfortable (if no less funny), a series of vignettes that explore the hollowness of privilege, the toxicity of comparison, and the melancholy of accomplishment.

Medallion Status tells the story of Hodgman's post-TV life. After lucking into a role in a series of Apple TV ads, Hodgman went on to semi-regular stints on The Daily Show under Jon Stewart and a series of medium-sized parts on well-regarded sitcoms, but these have dwindled, and while Hodgman has many other claims to accomplishment and fame, they're not TV fame (and arguably, as Hodgman points out, even TV fame isn't TV fame anymore in our fractured world of streaming services). TV fame is a weird kind of fame, a stopped-in-the-street kind of fame, a fly from New York to LA every week and stay at the Chateau Marmont kind of fame. It's the kind of fame that gets you invited into the swag room at awards-shows where you can be measured for complementary custom-made leather shoes or take home a really amazing pair of jeans.

For Hodgman, as riven with insecurity as the next person (especially if the next person is a white, straight dude from a middle-class background who has a keen appreciation that he's living life on the lowest difficulty setting and is likely being serviced and fawned over by people who work harder and are more talented than he is), the gradual withdrawal of the trappings of privilege are a constant, nagging confirmation that every jolt of impostor syndrome you've ever felt was fully deserved.

This becomes the basis for an extended meditation on the many ways in which privilege feels gross and upsetting for the privileged: the systems around you are designed to tempt you to strive harder to attain the next level of privilege, where, you are assured, you can rest up from your anxious climb and enjoy the summit. But each summit reveals another summit, and higher, more promising, more tantalizing summits you can attain.

This is both the literal and metaphorical life of a frequent flier, of course: each tier in the airlines' customer loyalty program is designed to remind you of how terrible things are on the tier below you and how marvellous things would be if you could only rise up by one more level. And each tier is designed to panic you as the year progresses and you realize that you might not re-establish your status. And it is status, exclusivity, a secret society for one percenters, celebs and looters, all rubbing shoulders and eating chef-prepared meals and drinking free whiskey at 30,000 feet in a lie-flat bed.

At this point, you might be thinking that if being privileged is such a burden, you should try having no privilege at all. Hodgman agrees with you: indeed, the story of Medallion Status is about how badly this works out for everyone.

From his perch on the middle tiers of celebrity, Hodgman is able to compare himself to people who are in much smaller cohorts than his own: if he's in the 15% of people-on-TV, he's comparing himself to people in the 5% or even 1%, and yet, whenever he comes close enough to tug at those tailored and exclusive shirt-tails, he realizes that those people are every bit as miserable and insecure as he is.

And therein lies the message of Medallion Status, latent amidst the very funny jokes and the charming asides and the disarming honesty: that the whole system of privilege and inequality isn't serving anyone: it makes you miserable to be at the bottom, sure, but it also makes you miserable to be at the top.

And worse: as Hodgman travels through, and finds some accomodation within, these rarified heights, he sees how privilege turns the privileged into monsters, including Hodgman himself, whose impulses are warped and stunted under its ferocious gravity. As funny as Hodgman is -- and he's very, very funny -- there is a kind of horror in this book, something appropriately Lovecraftian (given both Hodgman's dedication to New England and Lovecraft's revolting worship of elitism). What Hodgman describes is a horror-movie form of compartmentalization, in which the protagonist finds themself committing terrible acts, knowing that they are terrible, unable to stop themselves.

My absolute favorite mode of humor is "ha ha only serious." One of Hodgman's anxieties is that he's not serious enough to be a comedian: that making a career out of inventing untrue facts about orchestral instruments or being the straight man on The Daily Show makes you funny, but not a comedian -- not someone using humor to disarm power so that it can have truth spoken to it.

But Hodgman is speaking truth to power here: he's spilling the rich, white guy tea, which is that they're absolutely miserable. Not that the wealthy and powerful deserve our sympathy -- but it's important to understand that the system is frailer than you think, because the only reason its supporters defend it is because they're afraid that if they're not defending the hierarchy, they'll end up on the bottom of the pyramid.

This is the moment for that message, with an election only days away and the most egregious example of self-parodying, useless and overprivileged whiteness in the White House. Trump's whole "poor person's idea of a rich person" schtick is the living embodiment of the idea that comparison is the thief of joy. Trump is insecurity manifest, a would-be dictator whose manifesto could easily be titled Mein Angst.

The difference between a monster and a mensch is self-awareness. Hodgman's Medallion Status is the opposite of narcissism: it's an honest and terribly funny peek into a world that very few of us will get to see, one that is frank enough to admit that the only thing the people in that world enjoy about it is that we're not allowed in it.

Medallion Status: True Stories from Secret Rooms [John Hodgman/Viking]

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Medallion Status: comparison is the thief of joy, and John Hodgman is the thief-taker - Boing Boing