The carpenters were careful to hide their seams in this room: the brick insides are covered by a curtain of paint, the floorboards are free of splinters. Tonight the whole place gleams in waiting: the stage shaped like a crescent moon, the idle microphones , the rigid music stands. For once the Calhoun Cabaret will deserve its name: a comic troupe is filing its way into town.

LD Beghtol, the leader of the caravan, arrives after the moon has come out. From largest to smallest, his accessories include two musicians, a magnificently heavy duffel bag, a black instrument case, and a silver earring weighing down his right ear like a fishing anchor. Right away, LD notices the bubble machine placed onstage for his pleasure: “I used to pick out cute people in the audience and blow bubbles at them,” he remembers. The maroon of his newsboy cap matches the paint until all at once he takes it off and proclaims: “It’s all about me tossing my bangs seductively.” The back of his head is so closely shaven his scalp sees the light, while the front is a long horsetail he’s fond of swatting away with his hand. No time is lost unpacking the instruments: a collection of finger cymbals, a small family of guitars, a lonely electric bass. Sound check almost begins before the news gets around: they left the glockenspiel behind. A hush sinks in before LD decides it’s for the best: “Glockenspiels are so over!” he notes. “They are so over…” (this time less emphatically). Soon he brightens: “I’m excited about my Hypnotic Flange Petal. And the bubble machine makes up for all manner of my dimwittedness.” From his plastic bag he takes out a set of brown suede shoes: a little fresher, but otherwise identical to the ones he’s wearing. They’re part of his dress-up clothes, but later he’ll decide not to use them and perform in only socks.

With a pioneer’s face and a forest of a beard, LD could pass for one of his own ancestors. He looks like a Civil War veteran who’s spent the last few years drinking whiskey on the porch. If he had been born back then, he would’ve landed on the wrong side of the Mason-Dixon Line: LD comes from Fort Campbell, Kentucky, and grew up in Clarksville, Tennessee. He should be Appalachian and gruff, I think. Instead, he croons and plays bite-sized instruments. The shotgun I picture him rightfully carrying becomes a ukulele as it slides out of its case.

On the modest stage, the insistent bulk of LD’s body clashes with his little instrument. He holds it high against his chest, as gently as a new father would handle a child. “How’d you take up ukulele?” I ask him. “I thought I’d look really cute with it,” he admits cheekily.

When sound check is announced, LD plants himself by the microphone. In place of the customary numeric count, he makes a list of the things he looks for upon leaving his apartment: “Spectacles, testicles, wallet, watch.” Beneath the dwarfed mike, the cloud of his beard bobbles up and down in time to the beat of his words. The gentle woodsman has arrived with his buddies.

Playing and singing and cursing on stage, LD looks so strange in our century I have to rewind his steps to convince myself he’s not some Southern ghost. In my mind, he walks backwards through the major streets of New Haven, past the tattoo parlor and cigar lounge. The doors of Union Station close behind him; he goes down the up escalator before landing again in the straight-backed orange chair of the departing train. Then he’s sailing past Connecticut towns with Puritan names like Milford and Greenwich and funneling back to Manhattan before the high ceilings of Grand Central greet him. “I came to New York in 1995,” LD shares, “and I had a really easy time finding like-minded people who wanted to play music too.”

LD is the founder of Flare (or Flare Acoustic Arts League), which began in 1996 with his friend Damian Costilla as a house of musicians with a revolving door. Charles Newman, who plays keyboard and co-produces the tracks, came to replace Damian as LD’s main collaborator over the years. “Everyone who was in Flare is still in Flare. It’s not like we run through people, they come and go,” LD proclaims. “But I hate the term collective, not being a hippie and not being 22. I’ve never played hacky sack, and I’ve never even smoked pot.” His current bandmates have pet names that sound like Italian gangsters hired to play music at a hoedown: Ernie, Vinnie, Hollie, Pinky (the last one fiddles with viola, Stroh violin, and an unexplained collection of “toys”). Flare is orchestral pop: a swish of strings, touches of keyboard, and always the surprising polish of LD’s voice stacked against his rural looks. LD trades on his voice. His baritone ranges in mood from ’30s tenor to ’50s rockabilly to Gilbert and Sullivan. And he still gathers people as he goes along: Tonight it’s Geoff Otis and Chuck Plummer, one a Vermont college student, the other a harmless man growing into his thirties in a Red Sox cap. Together they form a temporary permutation of LD’s other band, LD and the New Criticism, which he started because Flare’s tightly-packed chamber-pop songs can be so difficult to arrange: “I wanted an excuse to be funny.”

Still on stage, it’s as if LD has forgotten that it’s only sound check. He strums a thumping and ethereal beat on his ukulele. His delicate hands are so shrunken against his body that I think of a musical Tyrannosaurus Rex. When rehearsal ends, LD hugs his wooden instrument close and decides: “If they’re train wrecks, they’ll just be train wrecks.”

We move to the Stiles common room for a book reading before the concert. It’s a place with sterile clusters of chairs and even worse lighting. Safe on the only comfortable couch, LD tells us something about his roots: he admits to having mostly “horse-stealing, alcoholic relatives.” His great-great-grandfather, though, was the white sheep of the family, a teacher and master of the schoolhouse where Abraham Lincoln learned to read. I imagine LD dressed in a top hat too, and this fluorescent place suddenly becomes a one-room country classroom. He would be the kind of teacher to bring his kids snacks, passing the warm dishes from lap to lap: “I make the best gingerbread in the world. It’s all brown sugar, unbleached flour, spices, butter and molasses: it’s very cakey and moist.” It comes from an old 1880s recipe, I learn, that mothers used to wrap in brown parcels to send to their daughters in boarding school.

But here there is no hint of a fire or log walls. The audience is a predictable set of self-stylized (yet deeply nerdy) hipsters. LD sips his coffee daintily and admits: “I’m deeply horrified of performing.” But his reading betrays nothing. He shares pages from his new book about his best friend and collaborator Stephin Merritt’s band, the Magnetic Fields. It’s a field guide to their album “69 Love Songs” (a slyly-named three-disc epic) and part of Continuum’s series of books about obscurely famous albums. “Writing the book, I was trying to track down strangers who were fans. I was interested in any anecdotal evidence about the songs: This is how I seduced my boyfriend, this is how I drove my roommate crazy.”

LD and Stephin found each other back when cassettes were still the musical currency. The two met “at this horrible restaurant. Six of us were sitting around eating tepid, hideous vegetarian food.” But next thing he knew, LD was singing on the album which has become a cornerstone of any indie pop lover’s collection, trying on a sad cast of lovelorn, lovesick and loveless characters. Both musicians know how to fold their sadness into a deceptively beautiful chest of drawers.

When the reading wraps up, we rush back to the Cabaret only to greet a room that remains empty for another half-hour. Finally the spectators arrive, one by one or in groups of friends, and leave their early spring coats on the sidelined couches. With the room filled, LD casually crawls on stage. His eyelashes blink above the steady mantel of his cheeks, and his baritone travels all the way to the farthest set of ears. The background music is a simple dream of ukulele and mandolin. His first song opens with the line: “Imagine life lived like a poem/ A Pre-Raphaelite dream of love and beauty,” before crashing down: “But your life will never be a poem/ Because deep down you look like Howdy Doody.” As he sings, LD swims through heartbreak and death and comes out grinning. His songs betray a kind of irreverent mourning: “This is so depressing! It would sound great with clarinet.”

When the tune ends, LD turns and asks: “What’s next, Chuckles?” Their faces are unlikely matches for the genteel veneer of the songs. No slicked hair, no bow ties, they look like the kind of men lurking at every family reunion: distant uncles. Occasionally, the tattoo on his forearm flashes out, a crippled angel with crutches and a fragile sling. He introduces the next song with the line: “Here’s a happy little song about suicide,” and counts off with a “1, 2, 7, 8, 12… We’ll make this up as we go along,” he adds. He sings: “If you love me baby, flip the switch,” and goes on to names various ways of dying: dropping off a bridge, being buried beneath a pillow, snapping the feeding tube in two; the list becomes absurdly inventive. Depression and anxiety, loneliness and failed romance: Although most people take these themes heavily, LD treats them as the best materials for comedy. His black humor is all the more effective against the Irish Spring freshness of his croon. When the song is over all he can say is: “I’m so glad you’re laughing,” pleased that everyone got the joke.

For the last song, “Love Finds Andy Warhol,” LD recruits his audience members again, this time to shake, rattle, and pluck things along with him. On the edge of the stage I’m soon dancing in place and slapping a tambourine against my leg. Others are playing hand bells and guitars and an extra ukulele. It’s a tentative circus. No one wants to skip a beat or invert a chord, but as LD sings he reassures us: “Everyone’s a Superstar, everyone’s a poet. Everybody’s like me and you, pet/ But they don’t know it.” Still, he is the core beating at the center of his small mad circle, and it’s the rest of us who’ve been invited into the set. As the song goes on, we grow more festive. Our coltish feet begin to stamp, our faces loosen. Soon, we could be at a cabin-raising in the middle of the woods. We should have brought along casseroles for a pot-luck dinner. I imagine our jeans dissolving into gingham dresses and proper trouser legs, our sneakers replaced by brown suede boots. Suspenders and bonnets begin to appear in the cramped air. The chairs slide back and fold themselves away, and suddenly the floor is a quilt of hands linking up in pairs. On stage LD is a mountain man transplanted north to sing for a country dance, fiddling in plaid while couples swirl beneath him. Directing us to dance and feast and laugh while we still have our voices.