Much like a gifted kid who studies exhaustively for the spelling bee and then blows the two-syllable word, the roots rock-inspired hippie Todd Snider seemed unprepared for his close-up on The Late Show With David Letterman earlier this fall. Snider is a certified ace at performing troubadour style–just his voice, wits and a guitar. But for his national television debut he assembled a band, to which the show’s cameramen responded by shifting the performance’s focus away from him and toward guitarist Will Kimbrough, who was considerably more animated. By the end of the three-minute ditty “Unbreakable,” you’d have been forgiven for wondering why the shoeless slacker-type with the too-cool fedora obscuring his eyes was deemed worthy of a segment at all.

The millions tuning in might not have known that Snider’s missed opportunity was almost the latest peak in a midcareer renaissance. A 40-year-old whose upbringing in Bible Belt boomtowns brought him to his current home base near the ghetto in East Nashville, Snider has spent the past decade and a half barnstorming across America. Along the way, his half-dozen or so record-label affiliations have earned him a coterie of mature loyalists, the kind of folks who understand that the circuitous road to success is paved with richly detailed songs. Snider’s latest release, The Devil You Know, isn’t his first disc on a major label subsidiary–that distinction goes to his mid-’90s stint on Jimmy Buffett’s now-defunct Margaritaville Records. But like its 2004 predecessor, the masterful East Nashville Skyline (recorded for John Prine’s Oh Boy! imprint), the album has inherited the yarn-spinning of the Nashville-outsider genre alt-country while dispensing with the romance of outlaws and losers that often makes the genre seem both wrongheaded and condescendingly boho. “I want to know if you belong or feel abandoned,” Snider writes in the new album’s liner notes, quoting poet-spiritualist David Whyte. In its effort to parse hard truths about survival in Bush’s America, Snider’s music stands alongside the work of artists like Buddy and Julie Miller, Gillian Welch and Rodney Crowell as part of a God-fearing country-and-western left wing that carries even more creative weight than twangy cause célèbres Steve Earle and the Dixie Chicks.

And yet Snider would be the first to admit that his audience, for all its devotion, does not always agree with him. These days, one of the staples of his live set is a comic provocation from East Nashville Skyline called “Conservative, Christian, Right-Wing Republican, Straight White American Males” (check the video-sharing site YouTube for a clip). Although Snider’s charm gets him through it whether he’s gigging a roadhouse or a more formal concert venue, he recently told an interviewer from No Depression, a bimonthly publication devoted to American roots music, what happens later, offstage. “There’s a part at the end of the show where you get to meet people,” Snider recounted. “They like you, and you go from that element to the hotel or wherever. In between, there are people that are mad. And they’ve got a half a minute a night to go tell me I’m a dick…. I always just think, ‘I wish that guy hadn’t called me a dick.'” Ultimately, the songsmith is philosophical about it: “If the idea that you were a dick overwhelmed your show, though, that’d be something you’d have to address.”

Notwithstanding the subjects in “Conservative, Christian,” most of Snider’s recent characters are hard-luck types. He breathes quite a bit of humanity into portraits of men and women taking repeated trips down the low road, which suggests that Snider is well aware that life can’t be so bad if your major complaint is that someone called you an expletive after a sold-out show, or that you came up short during a TV appearance, or even that Garth Brooks scored a hit with a melody that was legally pilfered from you. That last fate befell Snider as a result of a bizarre turn of events that he now mines for comedy when introducing his new song “If Tomorrow Never Comes.” Details are sketchy, but the upshot is that the melody of one of Brooks’s earliest hits–a ballad also titled “If Tomorrow Never Comes”–bears an eerie resemblance to Snider’s frat-boy anthem “Beer Run.” Snider has never taken legal action against the Brooks collaborator credited with the alleged theft, but he states plainly both onstage and in the liner notes to The Devil You Know that his new song–a sort of Jerry Lee Lewis-style mix of hymnal and raucous fire–is a somewhat laughable attempt at stealing the melody back. It’s a “way to let the guy know that I love him and his version of ‘Beer Run.'”

It would seem that bitterness isn’t in Snider’s vocabulary; revenge fantasies certainly don’t haunt his sleep. As a poet of those doomed to make the worst choices from among very limited options, he’s even willing to entertain the idea that some other guys who stole from him–at gunpoint in a Memphis back alley several years ago–might have it a lot worse than he does. Memorializing his mugging in a new song called “The Highland Street Incident,” Snider casts himself as the gang’s ringleader, not the victim. The crunch of the piece’s guitar tremolos place an eerily accessible shine on the sociopath’s powers of persuasion. “It was harder to imagine/Than it was to do,” the protagonist reminds his skeptical cohorts about the deed, though it’s unclear whether Snider is referring to his own meeting with the bandits or a caper that preceded it. He won’t make excuses for them, though. The pretzel logic in the chorus is a harbinger of other victims to come: “Did we get arrested?/No, we did not/We didn’t shoot anyone/Didn’t get shot/Didn’t hurt anyone/At least not a lot/And we got what we wanted.”

Snider performed that song to what seemed like stunned silence at the Canal Room in New York recently, and thankfully the quiet was more attentive than hostile. His profile has grown both critically and commercially since the release of East Nashville Skyline, and the smartass cool he maintained before this record has given way to politically charged wit; even a lovesick piece like “Carla” alludes to forms of triangulation. (“Tryin’ to fill my head with doubt,” he reminds the woman who took her sweet time leaving him. “You nearly had me walking out on you.”)

Given the presence of Al Franken on Letterman’s couch the evening of Snider’s visit, it’s safe to say that those who tuned in to see the singer were hoping he’d stir up partisan trouble by playing “You Got Away With It (A Tale of Fraternity Brothers),” a folk ballad that has been making the rounds of lefty radio and blogs since the spring, well before The Devil You Know was released. More of a voiceover with strumming than a song, the piece apotheosizes the most engaging qualities of his performing style: His plain-spoken delivery draws you in, while his guitar facilitates confession, reflection, rambling. Snider’s first-person narrative of a wealthy aging man reminiscing with an old friend about a shared past of hippie-bashing, alcoholism and other secret misadventures turns somewhat acidic at the end, when the narrator lets on that his smooth-talking drinking buddy now has the run of Camp David. While Snider may be guilty of preaching to the choir with his Dubya allusion, the ploy makes the track funnier because it’s less, rather than more, believable. It’s pure fantasy, and Snider knows it. The song’s last line (“You’ll get away with this new thing, too”) is too vague and cryptic to be a true zinger (is he talking about Iraq?), but doubtless all kinds of couch potatoes have heard it and shaken a fist at the television, whether in anger or solidarity.

In the end, the songwriter’s flair for the absurd may be what separates him from the average folkie or country singer. Both the new album and East Nashville Skyline suggest that while maturity (and more than one stint in rehab) has transformed Snider from barroom wiseacre to keen observer of life at the fringes of the workaday American mainstream, his comedic chops have become sharp enough to rival Randy Newman’s. In “Sunshine,” for instance, a potential suicide enjoys a beer on a ledge as a crowd of people gathers down below–some of whom suggest that he jump. How does he feel? “Like captain of the team.” Then there’s the moment when the itinerant pool shark in “Just Like Old Times” nearly gets arrested in a motel room with a former teenage crush who now makes her living as a prostitute. “Don’t get all sentimental on me now, girl,” he tells her, after dismissing the cops by retrieving an old high school picture from his wallet. “You haven’t even told me what your new name is.” Taken together, it’s all of a piece with the lone lyric he raises his voice to sing somewhere in the middle of “The Devil You Know”: “There’s a war goin’ on/That the poor can’t win.”