If reading books were like watching movies or listening to music, I bet pop culture would be a lot different than it is right now.
Except reading books, for most people, necessarily takes longer than a few hours. Hell, reading books for some people takes months. What this means is that when you find a writer you really like, it can be a little complicated to read all of their works, especially if you aren't planning on just reading them. (Not to mention that one of the problems you're bound to face is that it's a lot harder to find all of an author's books than it is to find all of the movies in a particular sequence or all of the music from someone's catalog.)
Anyway, to cut that short, what I really mean to say is, I've just gotten around to reading my second Michael Chabon, after The Amazing Adventures of Kavalier & Clay, and that was a decade ago. I won't be reading another one for maybe another year or so (it's on the Reading List, so I know, and it's The Final Solution). Gentlemen of the Road, though, holds a fairly curious position for me. For dedicated Chabon fans, the essay he includes at the back of the book talks a great deal about how this story is a considerable detour from what he usually writes, or what he wrote last millennium, what he describes as modern naturalism, which is to say stories set in modern times using fairly common modern experiences (he lists divorce in his examples about a dozen times).
He also writes from a Jewish perspective, and isn't shy to admit it, and Gentlemen of the Road, he half-jokes, was almost called "Jews with Swords." From someone who read Kavalier & Clay (a book about a couple of Jewish boys creating a superhero called the Escapist in the Golden Age of comic books, around the same time as the debut of Superman, who was also created by a bunch of Jewish boys) first, it's not hard to see how Chabon ended up writing a period piece about Jewish characters, but that's exactly what my prior experience was. That one won the Pulitzer, and by definition has come to define his literary career, so it's not so surprising that he grew a little ambitious following it (not that he admits as such in so many words in that essay).
What Gentlemen of the Road really is is Chabon going full-ethnic, in the sense that he's no longer an American writer, but a Jewish one, regardless of the period setting. He's no longer writing modern naturalism, but writing, basically, world literature. That may be the real adjustment anyone needs to make in order to read it.
In many ways, it's not so different from what Marlon Brando did when he wrote (or started writing, which someone else later finished, and the transition is clear) Fan-Tan, a book that is chock-full of character details (in the beginning that reads like a typical Brando character sketch) but is otherwise a little aimless. Gentlemen of the Road is about a couple of buddies (which to my experience is the basic Chabon plot) who stumble into a series of developments that snowball into a story, but are really just a series of events, like The Canterbury Tales if each of the pilgrims were relating a single narrative from a different perspective (like a traveling Rashomon, but with plot points that advance rather than reiterate the action).
It's a little tedious, as Chabon immerses himself in details that makes for what some people expect as necessary literary window dressing, and one gets the sense that this is exactly what he was aiming for, to show off his prowess, but then, there's also just enough lucidity that it can also be described as comfortably obscure, the way comic book writers Grant Morrison and Paul Cornell write, so that you don't necessarily need to know or care about everything that's going on, so long as you can follow the thrust of what's happening. The buddies are ultimately detached from everything anyway, and it's enough to know that they survive some crazy things because that's what they do. There are some really good sentences.
Jews throughout history have been the pariahs of society, and part of the reason why is that they've made an artform of sticking to their own. It may be safe to say that the modern entertainment machine has produced more visible Jews than at any other point in history, because entertainment is the only place where you can hide in plain sight, calling attention to yourself while calling attention to something else entirely, whether in a movie, a joke, or a book. Chabon wonders if anyone would take a Jew with a sword seriously, and the answer is yes, because they don't have to picture Woody Allen, even if he is one of the more famous Jewish entertainers today, or that we still have the collective hangover of the Holocaust to be reminded that recently Jews have still had a tough time of it, and that Israel is a country that's been besieged since its inception. You've got someone like Mel Gibson who can be accused of being antisemitic one minute and want to make a movie about Judas Maccabee the next. (This dude was a warrior badass in the Old Testament.) Not surprisingly, because most of us want to believe in only polarizing facts, he has not been able to make that film yet.
Yet that's exactly what Chabon is trying to work against in Gentlemen of the Road, to chip away at the culture of contradiction. There's a woman who pretends to be a man, even when the jig is up, throughout the book, and that's one of the best elements in it. Chabon claims that this is not the book anyone would expect him to write, but to anyone taking it seriously, it's exactly what someone in his position would have done, now that it no longer matters that he try and appease the literary establishment and instead write what every writer wants to write, something that has meaning to them rather than what some people thinks has more universal appeal. Kavalier & Clay was about comic books, which last time I checked was not exactly part of the literary establishment.
So long story short, I think Michael Chabon is probably worth the investment in time to read.