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What It's Like Living Your Entire Life in Pee-wee Herman's Shadow

"Pee-wee's Big Holiday" is a return to form for Paul Reubens, who happens to be my cousin.

Paul Reubens as Pee-wee Herman in 'Pee-wee's Big Holiday.' Photo courtesy of Netflix

When I was seven years old, I sent Pee-wee Herman a letter. The year was 1989.

You should know at the start: Paul Reubens, the actor by now better known as Pee-wee Herman, is my cousin.

We've never met, but he's the grandson of my maternal great-grandfather's sister—my second cousin once removed. Even though Isaac Milstein, my mother's grandfather, a self-made haberdasher who moved to Poughkeepsie, New York, from Kiev in the 1880s, was estranged from his sister, Reuben's mother, Pee-wee has always loomed large in our family.


Postcard from Paul Reubens in 1991. Courtesy of the author

We've often said he's in our genes.

He's there, in our aquiline noses and foreshortened jawlines, in our long Dumbo ears and pronounced nasal cartilage. He's there, too, in the faintly spasmodic, gurgling, and sometimes involuntary laughter we unleash at weddings, bar mitzvahs, even funerals. ("So you're a Milstein? Laugh like one.") And in the tacit acknowledgment: He made it, where so many others less talented didn't. In the hard-won insight, we Milsteins all carry that human existence is no more than this: to be full grown and childlike, a fool and a wise man. Pee-wee is all and yet none of these things because Pee-wee exists in a liminal state: Faulknerian man-child and dandified gent, permanent bachelor and neighborhood creeper.

And this is what renders his humor effective, how Pee-wee's dichotomies square up with ours. They drive us outside of our most cherished selves. They make us laugh at what we're not.

Pee-wee's Big Holiday, Reuben's most recent reprisal of the character since the Pee-wee Herman Show in 2009, is a fittingly weird comeback in the form of a homoerotic road movie/love story, Peter Pan as imagined by John Waters.

At 63, Reubens has been digitally altered to appear younger, and the effect is that he appears ageless. His suit is still smart, and his eyes are still bright, if a little world-weary from all that they've seen. An effete, well-heeled bachelor who lives, much like the actor himself, in a superannuated efficiency apartment, Pee-wee flips pancakes and flattens grilled cheeses at the local greasy spoon in Fairville, a cozy small-town paradise in Anywhere, USA. Pee-wee rides not a bike, but a toy-sized red sports car. He tows an old woman downtown on a skateboard. "Is there anything sweeter than you?" she asks Pee-wee. "A root beer barrel," Pee-wee responds.


Later, when a fellow Fairvillian asks Pee-wee, "Don't you ever wonder what life is like outside Fairville?" Pee-wee's assured response is "Nope."

Enter Joe Manganiello, of True Blood, White Collar, and Magic Mike XXL fame, pectoral and scruffy where Pee-wee is prepubescent and smooth-skinned. He parks his Harley at the diner, Pee-wee suggestively makes him a milkshake, and the plot is off and rolling.

Here's Manganiello on his Harley, tandem-riding with Pee-wee, his helmet strapped tight. Here's Manganiello, built like a Greek god, asking Pee-wee to come to his NYC birthday party, and the rest of Big Holiday is Pee-wee trying to make that schlep to the Big Apple. Judd Apatow co-produced the show, and so it bears his warm, fuzzy stamp, but also his irreverence. Pee-wee is a perfect fit for Apatow's formula, a man-boy with a heart of fool's gold.

The episodic narrative turns picaresque as Pee-wee gets closer to Joe and his Tribeca loft bash. En route, in true Pee-wee form, he becomes an accomplice of female bank robbers, gets abducted by bikers, is prized by the Amish, is flown across the Atlantic in a rickety biplane by a woman named Mrs. King, and gets trapped in the depths of an NYC sewer, where he suffers dark visions of Abraham Lincoln and a foul Queen of England with small mouths for eyes, recalling the undead night-trucker Large Marge.

In a dream sequence that prefigures their Manhattan reunion, Manganiello and Pee-wee ride purple piñatas. Their steeds equipages ejaculate sparks as their lances push out toward each other, erect.


When Joe Manganiello and Pee-wee, at last, are sitting in Joe Manganiello's apartment, trading friendship bracelets in the candlelit dark, and Joe asks Pee-wee: "You know what would make this perfect?" And Pee-wee says, "Yep." And Joe says, "Root beer barrels," revealing small straws in the palm of each hand that they jam in the top of the candy and slurp, you finally start to get the joke.

While Joe Manganiello gets older and wiser, Pee-wee Herman stays the same.

Pee-wee answered my letter a couple years later after I wrote it, in the fall of 1991.

This was by postcard—a black-and-white glossy. Its top-right corner reads: "Hi Cousin Adrian!" In it, the actor is sitting on Chairy, his sentient easy chair playhouse companion, and the shot has him posed with a quill and a notepad, his white platform shoes barely touching the floor.

This was, of course, around the time, under painfully dubious circumstances, that Reubens pled no contest to a self-abuse charge in a Florida theater. There were eyewitnesses, a security tape, grisly mugshots where Pee-wee looks like Steve Buscemi at the end of Fargo, but with much longer hair.

"I found my red bike and it's in the garage," Pee-wee's letter informs me—I'd asked him about it.

Uneasy at what my reaction should be, I never wrote my cousin back. The stakes were too high—what was I, a nine-year-old, going to say?

That was before I realized that Paul Reubens is but a man, after all—appetites, missteps, enhancements, and all. These days I prize the postcard as a family memento. Perhaps one day, I'll have it framed, hang it on my study wall.

"Paul Reubens," the base of the frame might read, "born that he might live again."