So it's no stretch that the folk singer's first album of new compositions in eight years, “Lifetime Achievement,” is loosely based on turning 75. It's on sale Friday.
The new song “How Old is 75?,” where he sings, “in five years I'll be 80. I'll hear the fat lady,” is one of Wainwright's signature mixes of humor and poignant observation. Three-quarters of a century is a milestone, not just because it's a big number, but because he's now lived longer than his father and mother.
“The aging thing has always been on all of my records,” he said. “But actually, it really applies to me now.”
Over the course of 15 songs, Wainwright sings about pieces of his life scattered in various locales, walking through an old lover's town, imagining himself at the gates of hell and the perspective of a dog caught in the middle of a divorce.
The title cut's narrator realizes that all of life's momentary achievements mean little next to love — either from a partner or audience, depending on your interpretation.
And family. Always family.
Anyone who's listened to the man that Rolling Stone called “the poet laureate of family dysfunction” knows about the competition with his father, his divorces from singers Kate McGarrigle and Suzzy Roche, the damage caused by the distant upbringings of son Rufus and daughter Lucy, both accomplished artists of their own.
Wainwright quips about “a couple of tense Thanksgiving dinners,” but is endlessly drawn to his own life for material, reasoning there will always be listeners who can relate.
“How could I not write about that?” he said. “What's a better topic than that? I could write about imagining what it's like to ride the rails or pick cotton. I'm just writing about what happened to me. That started at the very beginning; I wrote my first song about going to boarding school in Delaware.”
“Lifetime Achievement” is essentially Wainwright and his guitar — or banjo on “How Old is 75?” — with adornments added later. He usually performs alone, so starting alone is the approach that he feels fits best in the studio.
Wainwright “was something like an old man even when he was young, so he takes to the subject of aging with grace and insight,” music critic Stephen Deusner wrote in a review of the album for Uncut.
The singer grew up in the New York City suburbs of Westchester County and now lives on the eastern end of Long Island. He jokes about fitting in an interview along with “maintenance visits” to doctors in a trip to the city.
He can remember specifically what made him want to be a performer. At age 7, he sang a song to his mother and her sister, bathed in their adoration, and knew he wanted that feeling again.
Throughout his career, Wainwright has been able to toggle between humor and seriousness in a way uncommon to most songwriters.
The new “Fam Vac” is laugh-out-loud funny: the narrator wants a vacation from, not with, his family. At the same time, the way he sang of feeling adrift following the death of his mother in 2001's “Homeless” is chilling in its naked emotion.
“I think of myself as a switch-hitter,” he said. “I can do funny, and I can do really down and depressing. I'm goofing on it now, but I can do very serious songs. I decided I can do both and I have done both.”
It can be a tough line to walk. When the novelty song “Dead Skunk” became his first hit in the early 1970s — his only hit, really — that briefly became a trap.
His record company was unenthused when Wainwright suggested his breezy “The Swimming Song” as a new single; they wanted another silly animal song. The last laugh: 50 years later, “The Swimming Song” has more than 17 million plays on Spotify; “Dead Skunk” is at 3.5 million.
Wainwright's 76th birthday is coming up in a few weeks, right when he's heading out on his first post-pandemic tour. He's starting in England, where he generally draws larger audiences than at home.
“I'm so delighted when young people come up to me and say ‘my mom loved your records’ or ‘my grandfather loved your records,’” he said. “And then they say, ‘but I love your records, too.’ That, of course, is the most exciting thing. Then I feel like I'm 22.”
Wainwright never figured he'd be making music this long. While going out on the road is much harder, and Wainwright can see a deadline coming on that part of his career, he expects to write songs as long as inspiration strikes.
“When you start out in show business, or any business ... you have your fantasies about how big it's going to get, how famous you're going to get, how much money you're going to make,” he said. “I had all of those. I hoped that I would make a little more money than I have, but looking back, it's been great. I got to do what I wanted to do.”