THERE ARE limitless backhanded literary compliments in this world, and perhaps the backhandedest (shut up, it's a word if I say it is) of all is "He's a writer's writer." Sure, it sounds nice, but the unmistakable subtext is always going to be "His work appeals exclusively to drunken neurotics who will never be able to actually afford his books anyway."

So I won't call Charles D'Ambrosio a writer's writer, and not just because he would never use a fake-ass word like "backhandedest" for a cheap laugh, though he wouldn't. It's true that other writers tend to idolize the Seattle-raised, Portland-based essayist and short story writer, but it's the kind of admiration that's (mostly) free of the spite and jealousy that pretty much marks everything writers say about one another.

Writers don't resent him; they want to be him. He inspires a sense of possibility in everyone who reads him, and nobody who's ever read him can forget him. Writers love D'Ambrosio for the same reason that readers do—he makes literature a more expansive, more generous, and better place.

D'Ambrosio first appeared on the literary radar with his excellent 1995 short story collection, The Point, which was darkly funny (see "American Bullfrog") and darkly dark (see the title story, especially if you like crying). His second collection, The Dead Fish Museum, came more than a decade later, and somehow managed to surpass the first one. Both books stunned critics and readers, but it was his 2005 essay collection, Orphans, that swiftly became a cult classic. Published by tiny Portland indie Clear Cut Press, the book sold out of its small-print run and was never reprinted—copies of the original book now fetch up to $150 online.

The book's scarcity left a huge hole in contemporary creative nonfiction, for everyone except super-rich book nerds, who tend not to exist. So fans of D'Ambrosio were understandably freaked out (in a good way) when local publishing heroes Tin House announced they'd be bringing back Orphans—with six new essays, and a new title, Loitering: New and Collected Essays—this November.

D'Ambrosio hasn't published anything less than brilliant, but Loitering is remarkable even by his standards. The essays cover a wide range of subjects—the children who live in a neglected Russian orphanage; a company that makes those depressing prefab, suburban homes; the trial of Mary Kay Letourneau, the teacher famously convicted of raping her 12-year-old student. Many of the essays—perhaps all of them, depending on how you read them—deal with his family and his childhood in Seattle. It all sounds desultory and disparate, but D'Ambrosio has a way of making the kind of connections in a single paragraph that most authors need a whole book, or more, to make.

And he's the kind of writer who believes in the power of literature to make connections. "Alone," he writes in the essay "Whaling Out West," "you're vastly outnumbered; but in the company of another, by some weird miracle of human math, the odds seem wonderfully improved in your favor."

There's no denying that D'Ambrosio favors the dark and the elegiac; he writes about subjects like his brother's suicide and his difficult relationship with his father so forthrightly and fearlessly, I often wondered how he could finish a sentence without a series of small-to-moderate nervous breakdowns. (I've been working on an essay about my brother's death for more than three years, and I can't even click on the file name without wanting to throw up.) He disdains any attempts at easy answers, and favors the kind of ambivalence other writers try hard to avoid: In the preface to Loitering, he wonders, "where all the other people are who don't know, who don't understand. Are we—the hesitant, the conflicted—all alone?"

As dark as his writing can be, there are frequent flashes of humor. Writing about a Dallas haunted house run by Christians to discourage kids from having sex, being gay, or otherwise having any kind of fun, he describes the "by-now-familiar triad of fundamentalism, outsized Texas bullshit, and some of the lowest conservative clichés about life in the big bad world—basically an undiluted version of W. Bush, and as such, I guess, the potshots have already been taken."

Later, articulating the relationship that so many writers have with our fathers, he notes that his own dad has "never said a single word to me about my writing, except to observe that it's bullshit." Like a lot of us, he seems to share a sensibility with a character in his best short story, "Drummond & Son," who says, "I just start to laugh when I see something sad... I don't think I find it funny. But I laugh anyway."

It's that kind of passage that makes it impossible to feel anything but love toward D'Ambrosio, even though he was a better writer in his twenties than most of us will ever be. We laugh anyway, or we cry, but there's not much daylight between the two. You can wake to find your family, your entire world, shattered beyond repair, and you feel guilty about laughing, but you do it anyway, because it's better than feeling nothing. Alone, sure, you're outnumbered. But reading D'Ambrosio, you realize you're never really alone—or if you are, you can always make a connection to something. There's no writer like D'Ambrosio in Portland, or anywhere, and there's nothing backhanded about that.