I mention those two stories because they’re exceptions. Almost everybody I ask names the 2006 article on the Great Zucchini.

It’s not an immediately promising premise. The story is about a local children’s entertainer who is successful but disheveled. Forgettable fluff? Weingarten acknowledges as much in the story by including a conversation he had with a woman at one of the Great Zucchini’s shows. “You’re writing a story about him?” she says. “I mean, are you that desperate?”

She wants to know if there’s a hook. Weingarten assures her, and readers, that there is but that “it’s going to take some time” for the hook to be revealed. As the story unspools, we learn that the Great Zucchini, also known as Eric Knaus, is a troubled genius, a man with a nearly magical ability to connect with children, but also a man who is, by most adult standards, a complete mess. He earns six figures but has no idea where the money goes. His apartment is a wreck—the only food he has is a jumbo box of raisin bran. He’s afraid of commitment. His driver’s license has been suspended. All his appointments are in one book that, if lost, would likely ruin his career.

Weingarten writes: “I’ve known other men who approach Eric’s level of dysfunction, including myself.”

That last line is included casually, but it’s a confession. Weingarten sees himself in the Great Zucchini even though the Great Zucchini is barely able to cope with day-to-day life. And the more you know about Weingarten, the more that comparison makes sense.

Tom Shroder, Weingarten’s close friend and the former editor of the Washington Post Magazine, tells the story of when he met Weingarten back in the ’80s and had to scoop trash out of Weingarten’s car in order to sit down. He also remembers when Post employees had to move Weingarten’s desk to a different floor. When the workers saw the state it was in, with teetering piles of ratty notebooks and chewed-up pens, according to Shroder, they refused. The word “toxic” was used more than once.

During our lunch, Weingarten keeps tearing off little pieces of his dirty napkin, balling them up with his thumb and forefinger, and dropping them onto his plate amid the mashed remains of his mostly eaten lunch. It’s gross.

“Have you noticed what I’m doing as I’m talking?” he says, gesturing toward the mess. “Who does this? And I’m doing it as I’m telling you that I’m neurotic!” He then points to my pad of paper and says, “If I were writing this, I would note that.”

When Weingarten is reporting a story, according to everyone, he’s focused on that and nothing else. He ceases to be a human being—he becomes, in his own words, “the machine.” He hoovers up information and that’s it. Maybe he sleeps. Maybe he eats a sandwich. But mostly he does what he does until it’s done.

“He’s worthless when he’s reporting a story,” says Shroder, who considers Weingarten “hugely intelligent and hugely insane.”

Dave Barry writes the following in his introduction to Weingarten’s book The Hypochondriac’s Guide to Life. And Death: “Ask the many people who know and love Gene Weingarten if they think he is sane, and they will say, laughingly: ‘No!’ And then, after reflecting for a moment, they will say, seriously: ‘No.’ ”

So the messy, crazy, brilliant reporter profiles the messy, crazy, brilliant children’s entertainer. It turns out to be a weirdly ideal marriage of writer and subject.

Von Drehle, now an editor-at-large for Time, is the one who gave Weingarten the tip that led to the story. He had hired the Great Zucchini for a party and suspected the guy had issues. He didn’t know much more than that, but somehow it seemed like a Weingarten piece in the making. Like a lot of people I talked to, Von Drehle thinks Zucchini should have won a Pulitzer.

I’ve read the Great Zucchini piece ten times. Maybe more. But I’m at a loss when I try to explain why it works so well. There are awesome details, such as the fact that the Great Zucchini keeps his father’s ashes in a shoebox on the floor of his closet. There’s a road trip to Atlantic City, where the Great Zucchini gambles all night. There are startling scenes, including the conversation Weingarten has with the Great Zucchini’s mother about the death of the baby across the hall.

The sentences are pitch-perfect but not flashy enough to excerpt. Washington Post writer Hank Stuever refers to Weingarten’s writing as “almost devoid of lyricism,” a comment meant as a compliment. Each section of the article feels like a chapter in a novella. It’s about comedy, kind of. It’s about parenting, in a way. It’s about the lifelong reverberations of childhood trauma. It’s about forgetting to grow up.

But none of that captures it.

In the final scene, a little girl approaches the Great Zucchini and sticks out her finger, and the Great Zucchini grabs it. “Something indefinable passes between them,” Weingarten writes. Maybe the same can be said about what passes between the writer and the reader.