Thurs. June 14

"The strangest story ever told/Was how I got to be this old," sings Loudon Wainwright III, to begin his album, "Older Than My Old Man Now." You kinda get it right there, don't you? He's 65; his dad died at 63. "Here's another song in C, with my favorite protagonist - me," he follows up in "In C." Wainwright is someone I've known for years, as a fan, critic and interviewer, and one thing that was clear from the get-go:  Yes, he was a sharp observor of the world around him, but he wrote unsparingly about himself and his family. His romantic encounters - not often pretty. His dealings with his dad? Unpleasant. He even uses an audio snippet of his dad talking about his dad to open the new album's title track - "My father, who died when I was 17, remains my personal ghost." His own demons? "Tequila-ripped and on a tear," he sang in the semi-remorseful "April Fools Day Morn." Wainwright came from a famous family - his dad was the life columnist that shared his name - and he's the ex-lover of Suzzy Roche and ex-husband of the late Kate McGarrigle. He's father to Rufus, Lucy and Martha.  One of the most poignant songs on the new disc is sung with Lucy: "Love heels heartache and familial pain/And what family is not insane?" he signs in "All in a Family." (Martha and Rufus also join at later points.)
   Wainwright is at the Somerville Theatre Thursday June 14, sharing a bill with the nimble genre-slashing guitarist David Bromberg.
     It's funny. Wainwright primarily plays acoustic guitar - a folkie - but for years he abraded that folk community. He wasn't precious; he was sarcastic; he was brutal; he was comic. I remember he was one of the few folkies my pal at the Globe, Scott Alarik, reviewed unfavorbly. Scott and I were opposite poles on this one.
    Here's an excerpt from a review I did in 1992:
   When it comes to playing the class clown, singer-songwriter Loudon Wainwright 3d is still at the top of the heap. He sticks out his tongue; he scrunches up his body; he goofs on every possible folk-sensitive cliche -- including a threat, at Nightstage on Saturday, of playing a singalong rendition of "Kumbaya."

That didn't happen.

What did: Wainwright took jabs at the lonely folksinger/troubadour trip, one that he has been on throughout his life. "Actually," Wainwright said at one point during his 100-minute set "all these songs are about the same damn thing . . . isolation."

The tongue is in cheek. But just barely. Wainwright is semicarefree -- he's got an attitude. Wainwright is almost an antifolkie: as abrasive as he is warm, as sensitive as he is caustic. With "I'd Rather Be Lonely," "The Doctor" and "When I'm At Your House," Wainwright fused deep cynicism with fluid melodicism. "We're havin' some problems up here," said Wainwright, referring to his frequent guitar retunings. "But are you people from Julliard -- can you really tell?"

No. But you're still with the program.

Wainwright sings about a soldier's death in wartime; the pain that comes from a child's take on divorce ("Your folks fell in love/Love's a very deep hole"); his own ennui ("When I was your age I was a mess/On a bad day, I guess I still am"), and wallows in the sweet sadness of it all. Wainwright invokes Willy Loman, Genghis Khan and Jack Kerouac, and concludes "You start out a prince and you end up a toad." Wainwright's new album, "History," is yet another rough gem. He allowed, during the between-song chat, that he wanted to pump up its sales -- irony shaking hands with promotion.

"I don't know how to characterize it," Wainwright said backstage, of what he writes. "They're just songs from my cheesy little life. I'm not out to lacerate myself or anybody else. They're just topics I write about."
Tix: $37.50. Starts at 8.

55 Davis Square, Somerville, 617-625-5700 www.somervilletheatreonline.com