The Wikipedia entry for “Pee-wee Herman” begins by noting that the figure in question is “a comic fictional character” who is “best known for his two television series and film series during the 1980s.” The entry goes on to list Pee-wee’s species as “human” and his sex as “male.”

These classifications are true, for the most part, but they are also, as so many things are these days, complicated. Pee-wee, for all his human attributes, does not seem to engage in that most fundamental of human activities: aging. And he is a male who does not seem to be interested in that most fundamental of human preoccupations: sex. This—Pee-wee’s status as a man-child, a Peter Pan in pancake makeup—is the source of his charm; it is also, sometimes, the source of his menace. David Letterman, who first helped to propel Pee-wee—and his portrayer, Paul Reubens—to fame in the early 1980s, has observed that the character “has the external structure of a bratty little precocious kid, but you know it’s being controlled by the incubus—the manifestation of evil itself.”

That might be slightly overstating the case, but it helps to explain why Pee-wee has remained compelling and also confusing to audiences in the ’80s and ’90s and beyond: He embodies a tension that is understood both by kids who think the world is biased against them, and by adults who think the same. Every Pee-wee property (and there have been a lot of them over the years, from the TV show Pee-wee’s Playhouse to the films Pee-wee’s Big Adventure and Big Top Pee-wee) has somehow exploited that man-child dialectic. And you might think that the new one—Pee-wee’s Big Holiday, the Netflix feature produced by the bard of man-children everywhere, Judd Apatow—would be the most comprehensive exploration of them all. Here, you might think, is a perfect marriage of creators and subject matter: a film about an adult boy, created by people—the film was co-written by Reubens and Paul Rust, who, among other credits, was a writer for Arrested Development—who seem obsessed with the idea of, well, arrested development.

Certainly, Pee-wee’s childishness is on full display as he takes his Big Holiday. The plot goes like this: Pee-wee, frustrated to see everyone else in his hometown of Fairville growing up around him, has a chance encounter with Joe Manganiello (who is, extremely delightfully, playing himself (or, “himself”): a consummate Man’s Man, motorcycle and all, and also an actor who is extremely emotionally needy). Joe is having a birthday party in New York five days after he meets Pee-wee; in his capacity as a kind of karmic agent (a Hairy Godmother?), Joe invites Pee-wee to the party. (“The way I see it, Pee-wee Herman,” Joe sums it up, “you’ve got a choice to make: Stick around here, or live a little.”) And, because planes aren’t adventurous, Joe commands Pee-wee to make the trip on land.

Thus, a built-in bildungsroman, with the journey made via car and flying car and bus and river rapid and horse-and-buggy. Pee-wee’s trip features stops at a “snake farm,” and then an actual farm, and then New York City. It features encounters with a farmer’s daughters (because of course), and with the Amish (ditto), and with a wacky, aging heiress, and with the even wackier occupants of a mobile salon named “Free Wheelin’.” The trip offers Pee-wee, kind of, the chance to grow up.

Except: Does it? This is, throughout the movie, unclear. Here are some of the other things that take place over the course of Pee-wee’s holiday: Pee-wee rejects a woman who tries to ask him out; he develops a man-crush on Manganiello; he gets engaged, very much against his will, to one of the daughters of the farmer he encounters; and he has what may be his first kiss—with a bank robber (Alia Shawkat) with whom he shares an affinity because her nickname is ... Pee-wee.

One of the film’s many other instances of Pee-wee Ex Machina finds our hero, having arrived in New York, falling into a hole in Central Park. (It’s just there, perfectly Pee-wee-sized; don’t question it too much.) TV news crews find out about Pee-wee’s plight; they announce the news to their viewers with the chyron “BOY IN WELL.”

But, again: Is he a boy? It was, after all, mere moments earlier in Pee-wee’s Big Holiday that the Boy of “BOY IN WELL” fame was getting betrothed to a stranger. And, of course, the Boy in question has spent pretty much the entirety of his film dressed in that consummate uniform of masculine adulthood: a suit, a crisp shirt, a bow tie. And, it must also be said: The Boy in question is being played by an actor who is, no matter what good genes and good lighting and good makeup may have to say about it, 63 years old. It’s all a little too Cree-pee.

The to be sure part: The stage-in-life uncertainty here is, of course, at least part of the point. Pee-wee’s Big Holiday is on the one hand—like any Pee-wee adventure will be—a glorious, ridiculous monument to absurdity. Pee-wee will always be Dada. It’s silly to assign too much logic—too much cultural reasoning—to a character and a property that so insistently revel in their own madness. And there are, also, some decent jokes to be mined from the basic premise of a man-child navigating a world that that he doesn’t fully understand, and vice versa. When Pee-wee sits down to dinner with the farmer he meets, Farmer Brown, and his nine daughters, Brown asks him, “Would you like to say a few words?” Pee-wee doesn’t miss a beat. “Oh, sure,” he replies. “Encyclopedia. Pimple. And uh, hairball.”

It’s funny! And it’s revealing! It’s making fun of Pee-wee, but it’s really making fun of all of us—and of our participation in a culture that is so strangely eager for its young people to grow up.

But none of that changes the fundamental weirdness: Here is a now-63-year-old man playing a character with the cognitive and social acuity of a prepubescent boy. Here is that man-boy having an early, electric kiss with a woman in her 20s (Alia Shawkat is 26). It’s awkward, but perhaps not in the way Reubens and his fellow creators intended. “The last time Pee-wee was in a movie, 1988’s Big-Top Pee-wee,” the L.A. Times points out, “Ronald Reagan was in the White House and O.J. Simpson was making Hertz commercials.” (And also: Jessica McClure, or “Baby Jessica,” had just captivated the American public by … falling into a well.) Pee-wee might not have aged since then, but the rest of us have. We’ve become a little more sensitive—thus making the hairdressers Pee-wee encounters in the “mobile salon,” who are basically walking stereotypes of gayness and blackness, not just unfunny, but troubling. We’ve become a little more savvy—making the film’s many jokes about farts and screams and heavy-set women read not as slapstick, but as laziness.

Mostly, though, we’ve become a little more leery of the regressive politics that will be involved, implicitly and otherwise, when grown men act like boys. We’ve lost some of the patience we once had for people who can’t seem to figure out how to grow up. It’s a good thing Pee-wee Herman, the “comic fictional character,” is not fully human. Because really: Imagine if he were.