Brendan Benson walked up our three flights of staircase after having just ridden overnight from New York City where he and his crack ensemble had begun a short tour with an appearance on Late Night With David Letterman. He carried with him only one thing. Between the fingers, in his right hand, was a single wine glass that was a long ways from home. Cut into the tiny crystal goblet's bulb was the frosted insignia for The University of Virginia's John Paul Jones Arena, where the school's basketball team plays during the winter. It's a glass that's become displaced since a Raconteurs show in the recent past and it currently sits cleaned, perhaps a little cloudy from sudsy residue next to our coffee mugs near the bathroom. He brought his own wine and as the early evening worked its way into the middle parts of the evening, when dessert gets served and second winds crop up to put some life into the cheekbones, the bottle became less of a full bottle, but the songs that Benson chose on this night for his first Daytrotter session weren't at all the kind that are served over the seven deadly zinfandels, or chased by a rose. They are songs containing the kind of subject matter and all of the preoccupations that come with it that you tend to stew over some time later. They are the sorts of stories that sound better boozy and labored over. They are the songs of preoccupation, of strained sanity, of getting jerked around by the love bug. Benson is an absolute pop structure genius - from his days in Detroit, writing and releasing his solo records with a kind of relative anonymity that is disturbing and unkind, to his current situation as a member of one of rock and roll's more electrifying bands and best bud of fellow Nashvillian Jack White - and he interprets these contexts and overtures of extreme unruliness on the parts of one or two hearts shorting out to great effect. He sorts these swirls of fuzziness and arbitrary passion into verses that carry both lust, romantic thoughts and dejection, often just piggy-backing each other into a twisty cone of marksmanship. On his latest album, 'My Old, Familiar Friend, Benson has made it past the hours when the troubles or the confounding moments of a relationship - real or not - and he's just exercising all of the sparks and the wrinkles out with sharpened melodies and a soft voice. He's gotten to a point where he's been all in and given up on love so many times - seen the whites of love's eyes, stared into them, blinked and then has either bolted for the hills or getting torn apart by the illusion - that there's a lovely skepticism that's actually a working optimism. The songs on his latest album (three of which appear here along with a cover of the classic Superdrag hit "Sucked Out," which was learned by the band for the first time at the studio, with Benson learning the words on the spot) are wrapped around continuous struggle and adversity in emotion, sensing by the corners of the eyes that someone's gonna lose their shirt before it's all over. He's after the conundrums and into exploring the many, many ways that men and women have of acting the same way to one another - wanting each other, not wanting each other, falling madly, falling out brusquely, making it so easy and forcing love into being such a pain. There are shouts of glee and shouts of fumbling frustration - all of the exhaustion that takes the wind right from you. It's the land of the lost, with syrupy stains and sing-a-longs and Benson couldn't be a better host.