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.