Oedipus Wreck

Which is not really true. Wainwright toured constantly and made extraordinary albums for many labels, always exploring what he only half-jokingly calls "the family-kids-parents-death thing." Wainwright's songs about white-middle-class family life could be assembled into a theme album fully the equal of John Updike's Rabbit books, or, more appropriate to the moment, Jonathan Franzen's novel The Corrections. (Listen to a song such as "Hitting You," from one of his albums that cuts the deepest, 1992's History. The song is a merciless memory of losing his temper with his daughter--another Martha--and you'll know that no semipopular artist has sung more vividly about trying to correct life mistakes while further complicating them.)

Wainwright's career dips into unexpected pop-culture crannies. He sang songs as Capt. Calvin Spaulding on three episodes of TV's M*A*S*H in the 1974-75 season. National Public Radio commissioned him, in recent years, to write occasional topical songs, which were collected on 1999's Social Studies. In 1985 he wrote a song called "Hard Day on the Planet" after watching Live Aid on TV; it contains a now eerily prescient line about "hijacking airplanes and blowin' 'em up." After the World Trade Center attacks, he says, "I wonder if I'll ever perform that song again." On the title tune of Last Man on Earth, he sings, "I don't give a damn which idiot runs this country." "I wrote that during the [presidential] primaries," he says. "The other day I was singing the song as a guest on a radio show, and when I got to that line I thought, Should I be singing this? Then I thought, That's dangerous thinking." Self-censorship? "Yes. I should sing it."

If performing music is his steadying night job, he's pleased to have landed a day job on Undeclared. "I've been a huge Loudon fan for many years," says the show's creator, Judd Apatow, 33. "I wrote the part hoping he'd agree to do it. It was fascinating, because to the young people who make up the cast he was just this actor playing a dad; then I took them all to a show Loudon was doing [in L.A.], and they couldn't believe that this man singing these incredibly funny but cutting, painfully honest songs was the same quiet guy on the set."

And Wainwright, his Undeclared episodes in the can, is embarking on a tour whose tone will be set by the songs he's written for his mother. It was a tour he almost scrapped. "There was a feeling that without that person there, I give up, you know? I've never taken anything like Prozac--I fear being chemically altered, aside from glasses of wine and cups of coffee. I want to hold on to the lousy feelings." Wainwright, who was divorced in the early '70s, has fathered two other children (if you're keeping score, that's four) out of what we used to call wedlock; these days, he's an Undeclared dad, but one who summed up his daily life well more than a decade ago with a couplet on a song called, with typical irony, "Career Moves": "For 20-odd years I have strummed on guitars/Five thousand lost flat picks, four fingertip scars." When we leave the Oyster Bar, Wainwright goes to the coat-check booth, forks over his chit, and is handed an impressively large, ripped, battered, tan leather acoustic-guitar case. Slinging it over his shoulder and clamping on a middle-aged guy's porkpie hat, he lopes off toward the subway with a wave and a face crease that passes as a smile. He's an orphan troubadour, and not entirely unhappy about it.

More music news at www.ew.com(AOL Keyword: EW)