"I don't think longevity was ever a question, really. I've been an opera fan since I was 13. My mother and father were staunch folk-music nazis in terms of . . . ancient ballads and such," says the son of Loudon Wainwright and the late Kate McGarrigle. "The stuff we've been dealing with has been classic and solid. So the very first intention of all of our work is, 'Is this going to last?' "
The Garland repertoire is more than his having "the Judy gene" that gay men joke about being born with. He craves her classic songs and the superb orchestrations that came with them. Or rather, his voice does. He refers to it as an independent entity. It's also a "her."
"The singer in me is much more related to my subconscious. It's more animalistic, has its needs, requirements, and desires," he said the other day by phone from Milwaukee. "And I gotta keep her happy."
And fans have to be kept guessing as to what's next. As if recreating Garland's now-legendary 1961 Carnegie Hall concert wasn't audacious enough, Wainwright's 2012 "Out of the Game" video had his voice coming out of Helena Bonham Carter's mouth. (They're friends, and she has a great sense of humor, he says).
Behind all of that, though, is no Peter Pan. "I'm looking for something that can't be found on the main drag," is one of the first lyrics heard on his Out of the Game album. That shouldn't be surprising: He has more mileage than his breezy persona might suggest.
Wainwright has been performing and writing songs - with traction - since age 13. But one of his first claims to serious fame was his Poses album, in which he was self-appointed documentarian of the New York club underworld. His party days abruptly ended in 2002 with an odd combination of temporary blindness and hallucinations from crystal meth abuse.
You have to ask if he saw the late Amy Winehouse's life as a road he could have taken to the bitter end. In effect, he says, you have to be more famous than he for onlookers to allow such fatal indulgence.
"Let's be frank. We all know I'm successful, and I make a good living, and all of that. But by no means am I a world superstar. It's a blessing," he said.
For him, recovery from addiction translated into an outpouring of new songs, meeting and marrying Jörn Weisbrodt, having a child with Leonard Cohen's daughter, Lorca, and stretching his voice into the Judy Zone. He also came through the 2010 cancer death of his mother, with whom he was extremely close. It shook and changed his inner life, with an impact on his work that he's only begun to fathom.
"That really topped everything," he said, and made him look forward to a quieter life "when I can garden and look at birds. Or something."
Like writing an even grander opera. Though Prima Donna was an intimate day in the life of a singer who had mysteriously stopped singing prematurely, the next opera will have choruses and more characters. He sounds a tad apologetic about Prima Donna; though not widely praised by critics, it has moments of first-class Wainwright. And unlike Paul McCartney's classical compositions, Wainwright's actually sound like him. "That," he said, "is the best compliment."
But for now, his life is the road, partly because there's less and less money to be made with recordings. But the cities he regularly visits have their charms. In Milwaukee, he loves the Pabst Theater. And in Philadelphia?
"I dream of the cheesesteaks. Often," he says. "Too often."
Contact music critic David Patrick Stearns at email@example.com.