Sarah Vowell, The Wordy Shipmates (Riverhead Books, 2008)

How does Sarah Vowell do it? Despite her deep-seated geek tendencies, the writer and radio contributor has parlayed her persona into a best-selling brand. The Wordy Shipmates, Vowell’s exploration of the Puritans of the Massachusetts Bay Colony, is but the latest addition. For Vowell, these settlers—led by John Winthrop, who first described America as a “city on a hill”—are not only personally engrossing but a way to understand contemporary America. Take the Massachusetts Bay Colony seal: a picture of a Native in a loin cloth with the inscription, “Come over and help us.” This foreign policy—ostensibly benevolent meddling—has trumped what Vowell sees as the founding fathers’ call for isolationism. “For a ten-year stretch, the 1980s,” she continues, “Winthrop’s city on a hill became the national metaphor. And looking into the ways [his] sermon, or at least that one phrase in it, was used, throws open the American divide between actions and words, between what we say we believe versus what we actually do.”

That divide between actions and words is also the heart of the Vowell paradox. Although her prose verges on annoying, her sensibility is appealing. She grew up Pentecostal in Oklahoma, attending church three times a week, but is now a member of New York’s media elite. These kinds of contradictions run through The Wordy Shipmates: her account of the Puritans’ settlement in New England is not just a narrative but a scrutiny of personality and motive, filtered through her own fractured lens.

Vowell’s tone is conversational, intimate, filled with peculiar asides and so-called jokes: “I just feel sorry for [Roger Williams] that he lived in a time before air quotes,” and “severed body parts [are] the seventeenth-century equivalent of a gift-basket of mini-muffins,” and a lot of talk about sitcoms. The trouble is that Vowell’s writing reads like a friend who’s had too much to drink. In conversation—even on the radio—this style can work. In writing, however, it feels shallow.

“Here is a useful mantra,” she writes, “for maintaining some basic empathy for Winthrop and his English compatriots at their racist, persnickety, Indian-killing, puritanical worst: Harbottle Grimstone. [...]Is there a creakier, more British name? […] I would mutter ‘Harbottle Grimstone’ under my breath to keep in mind that these are more or less medieval people who are chronologically closer to Chaucer’s Canterbury Tales than to The Wire.” So do these sassy appraisals of history and wanton pop culture references fall flat, or do they make history zing off the page? I’m inclined towards the former perspective: I can’t help hearing Vowell’s voice in my head narrating her essays on This American Life, her timing slightly off, and the laughs accordingly sparse.

Yet somehow Vowell’s self-described “smart-alecky diatribe” develops into more than the sum of its parts. Despite her lefty politics, Vowell takes comfort in Winthrop’s words, especially after 9/11. And she supports American exceptionalism and the Puritans’ belief that their community, their future, was special. “Because even though my head tells me that the idea that America was chosen by God as His righteous city on a hill is ridiculous,” she confesses, “my heart still buys into it.” This is one woman’s idiosyncratic wrestling with history, her emotions, and book-learning, like combatants fighting to understand what happened nearly four centuries ago.

As a friend pointed out, Vowell is so comfortable in her own awkward skin that you cannot help but respect her. By the end of The Wordy Shipmates, she slowly, surprisingly won me over. Roger Williams, the Algonquin-speaking, separation-between-church-and-state-loving, hardnosed exile and founder of Rhode Island, becomes a character as nuanced and compelling as any in more staid historical writing. The author’s anguish over the lamentable fate of the heretic Anne Hutchinson convinces me too. And ultimately, Vowell does what she sets out to do: tell you a meandering, dorky story about a group of people who, for better or worse, shaped her crazy country.