Fly Fishing with Darth Vader: And Other Adventures with Evangelical Wrestlers, Political Hitmen, and Jewish Cowboys | By Matt Labash | Simon & Schuster | 336 pages, $25.99

Matt Labash has a nose for sniffing out the strange and the strangely compelling American characters, particularly those knee-deep in the tragicomic spectacle of our national politics. Fly Fishing with Darth Vader is a collection of his smart and often hilarious columns, all but one written for the Weekly Standard. In them, he faces off with a remarkable rogue’s gallery of subjects, including Dick Cheney, Donald Trump, Marion Barry, Christopher Hitchens, and Al Sharpton.

The book also includes less personality-driven pieces. There are satirical takes on Facebook and Canada, as well as an exploration of New Orleans after Katrina. And in his opening piece on Detroit, Labash spends some serious time in the Motor City, trying to understand how far things have fallen and talking to folks who are trying to rebuild or just get by. Rather than a fly-by-night tour of other people’s misery, the essay is considered and compassionate. It’s one of a few sober notes in a collection that is long on outrageous comedy, and an excellent illustration of Labash’s range.

Still, one of the unmistakable highlights is the title piece, which struggles with two facts: 1) Dick Cheney is a fly-fisherman and 2) he is very good at it. As a fly-fisherman myself, I must say I share Mr. Labash’s dilemma. If you fly-fish, part of you believes that no one who has the patience and determination to get out on the river and nab trout could possibly be one hundred percent evil. The whole process is just so Zen—you assume there’s some fundamental decency in other folks who practice it.

As Labash recounts, he managed to leverage his own passion for fly-fishing into a very, very rare interview with the vice president. The two venture out onto the Snake River in Wyoming, where Cheney proceeds to out-fish Labash by a margin I won’t even repeat. This provokes a goodly amount of cognitive dissonance for the author, who realizes that while he loathes at least some of Cheney’s politics, he actually finds him to be not such a bad guy to fish with.

This made me wonder whether the piece was trying to humanize Dick Cheney, or perhaps do something else entirely. We often hear that there are risks to “humanizing” someone, as if knowing that Joseph McCarthy flossed somehow makes him less of a jerk. Labash repeatedly turns this dictum on its head: many of his subjects are awfully “human,” yet this doesn’t make them any more sympathetic. Especially the politicians. Indeed, one of Labash’s great gifts as a journalist is to peel away the layers of spin and talking-point bluster—not to show you the sensitive soul underneath, but to really to get a look at the seamy side.

Some of the best examples of this occur on the campaign trail, with Al Sharpton or Arnold or the Donald. These portraits stubbornly hone in on everything the message-making machine tries so hard to eradicate. In a world of press conferences and weasely blind quotes, Labash is laser-focused on the humor and tragedy just behind the curtain. And if he can’t get permission to go behind the curtain, he’ll just boost an all-access pass, as he did during Schwarzenegger’s victory party.

The author’s love of outsize political characters is perhaps best captured in his profile of Roger Stone, a veteran fixer whose resume dates back to Richard Nixon. Stone’s appetite for electoral mischief and dirty tricks makes for a delicious read:

Except for the poster of a stripper he picked up in Amsterdam and a photo of him standing poolside with porn star Nina Hartley—she thrusting her glistening glutei at the camera, Stone peddling his own wares with his oiled-up frame packed into a banana hammock—his office is a Hall of Nixonia. I ask Stone, whose politics more closely adhere to Reagan’s, why he is such a Nixon fetishist. “It’s about resilience,” he tells me. “That’s the whole point of Nixon. Coming back from adversity. Coming back from defeat. Coming back from setbacks. It’s persistence. Obviously he was tragically flawed in a number of ways. Aren’t we all?” (It’s hard to tell when Stone stops talking about Nixon and starts talking about himself.)

Still, Labash has the patience and the skill to stick around long enough for the paradoxes behind the suit to shine through.

Toby Warner is a writer and editor living in Oakland, Calif. He is the managing editor of Boldtype, an online magazine about books, and a PhD candidate in Comparative Literature at UC Berkeley, where he focuses on Francophone African literature.