"When my mother died, I went into a tailspin," Wainwright says from his Long Island home. "I didn't feel much like doing anything, much less writing songs. I was living in England; I wound up moving home, living in the little cottage she had lived in."
That cottage, depicted in winter on the cover of Wainwright's new album, Last Man on Earth, is near Bedford Village, the Westchester County town where Wainwright grew up. The son of a writer and editor for Life magazine, and a descendant of Peter Stuyvesant -- a 17th-century administrator who briefly ran, for the Dutch, what would become New York state -- Wainwright has always mixed humor and autobiography in song. A contemporary of Steve Goodman, John Prine, and Tom Waits, Wainwright has put out 19 albums on labels major and minor. He had a novelty hit, "Dead Skunk," in the early '70s, and he's worked on Broadway. His songs have been covered by Johnny Cash, Marti Jones, Earl Scruggs, and even his son, Rufus.
Wainwright clearly doesn't lack for friends or admirers, but family is different. Martha Taylor Wainwright was "a big supporter of mine, and a huge, huge person, as everyone's parent is," he says. "Not to have her there, and to know it was forever, was very scary. There was a panic about it, like being a kid in a department store and not having your mother there."
With Last Man on Earth, Wainwright has reclaimed his muse. In addition, he's a burgeoning TV star, and he's in love. His humor now is tempered by a sense of mortality not unexpected in a man just turned 55.
"We were aware that the nature of this record is serious," he says. "Since, in the past, I've been somewhat known for writing funny or humorous songs, we decided to try to make [Last Man] a serious record. But we were also careful not to make it morose or a real bummer. We were very aware of trying to make the record not too long. I must have come in with 18 songs, but we knew we had a core and a theme, and we could set a tone if we used the 13 we did use."
So he, producer Stewart Lerman, and arranger Dick Connette, along with friends Suzzy Roche, Steuart Smith, and David Mansfield, crafted a poignant, melodic collection of confessional vignettes. They include "Missing You," a farewell to youth; "White Wine," a memoir of an affinity Wainwright and his mother shared; and the title track, a funny testimonial to Wainwright's simultaneously Luddite and postmodern nature.
The theme of Last Man? "It's a big word, but I go back to that loss thing," Wainwright says. "Being lost, losing someone, being at a loss -- whatever you want to call it. And some regret, too. I think the song, 'Surviving Twin,' is more about regret. That, of course, deals with me and my dad [Loudon Wainwright Jr., who died in 1988]."
Because Lerman has his own studio, Wainwright could spend more time on this album than on others he's made. "We worked on the record over a period of a year. Quite often, on records I made, you do them in three weeks and mix them in one week. One of the things that helped make this as good as I think it is, is we had the time to really get it right. That's not an easy thing, to have the time. Much less get it right."
Like James Taylor, a singer-songwriter who matches him in sensitivity, if not in lightness of touch, Wainwright has family in the business. Not only was he married to Kate McGarrigle (of Canadian duo Kate and Anna McGarrigle; they're now divorced); son Rufus is cutting a flamboyant swath through modern pop, and daughter Martha has her own musical career.
"They mostly grew up with their mom in Montreal, but I was on the scene summers and weekends and Christmas, and they lived with me in the summers in various locations," he says. "They know about guitars and fiddles and banjos; these are accoutrements in their lives, so it's natural for those two to go into the family business. It's a difficult life, and dangerous to a certain extent: late hours, strange substances, and funny inflations and deflations of the ego. But it's a great job, going out and performing and singing and writing and entertaining. It's also fortunate they happen to be very talented. It's possible, had they not been so talented, I might have discouraged them. But it was clear that they have real talent. There's the Oedipal struggle, of course, but I'm very proud of my kids. One of the things that pleases me most is that Rufus recorded my song 'One Man Guy' [on his album Poses]."
Wainwright has made the most out of fatherhood: He's a key figure in Undeclared, a new Fox series on which he plays Hal Karp, a somewhat dysfunctional dad. It's his first TV role since performing in a few episodes of M.A.S.H. in the mid-'70s. In reality, Wainwright takes fatherhood seriously. With actress Ritamarie Kelly, whom he describes as a "beautiful human being," he has an eight-year-old daughter. But, as if to show he hasn't become sentimental and soft, Wainwright can still deadpan -- especially when it comes to discussing his commercial success.
"I don't think I'll be thinking about making a record for another year, because I'm going to be pretty busy being a touring musician and a huge Hollywood star," he says dryly. "You got the parties; those Hollywood parties go on for days. The film festivals; I'll be out there in Cannes. Everywhere. It's saturation. It's going to be a good year. And maybe it won't. I'm smart enough for that, too. I'm feeling good. If my backhand was a little better, I'd be happier. But you can't have everything."