Loudon Wainwright III: ‘The good news is, think of all the cool people that have died!’

Loudon Wainwright III is letting me in on the realities of life at 75. “Just the other night I was moaning and groaning about my orthopaedic problems, my bad back and my hip which is probably going to be replaced,” he says, a subtle smile playing at the corners of his mouth. We’re speaking via video call from his home on Long Island. Over his left shoulder, an antique map sketches an aerial view of his surroundings in Suffolk County, the easternmost tip of New York state. “I was doing what we call the ‘organ recital’,” he says. “How many times I have to pee in the middle of the night, and all that.”

Pondering this irrefutable evidence of physical deterioration, Wainwright turned to his partner Susan Morrison, an editor at the New Yorker, and came up with some words of reassurance. “I found myself saying: ‘The good news is, think of all the cool people that have died!’” he says, a toothy grin finally breaking across his clean-shaven jaw. “If you think about it, Muhammad Ali is dead! Wow! William Shakespeare is dead. Katharine Hepburn is dead. It’s a pretty cool club!’” He pauses for a moment, spotting a flaw in his reasoning. “Adolf Hitler is dead too, but we’re gonna kick him out of the club.”

Wainwright has spent his life getting older and writing songs about it. He points out that the first words on his first record, 1970’s Loudon Wainwright III, were: “In Delaware, when I was younger…”. “Ageing and mortality,” he says, “Has always been in my wheelhouse.” Even so, turning 75 last September represented a significant milestone for Wainwright. It meant he’d outlived both his parents. His beloved mother Martha was 74 when she died in 1997. His father, the Life magazine writer Loudon Wainwright Jr, died of cancer nearly a decade earlier. Wainwright sings about them both on “How Old is 75?”, the wry penultimate song on new record Lifetime Achievement. “Mom made it to 74, though we all thought she’d get a bit more,” he croons over a rickety banjo. “My daddy kicked at 62 / Way too young, but then what can you do?”

One thing Wainwright did was write and perform a one-man-show about his father. Surviving Twin, filmed as a Netflix special in 2018, combined Wainwright’s own songs with spoken-word performances of his father’s columns, including his gorgeous 1971 obituary for John Henry, the family dog. “He was a terrific, terrific writer,” says Wainwright. “To have done that show and shared his work with people was really very rewarding.” He can see the similarities in the sort of writing they each produce. “He was a little straighter than I am,” he says. “He grew up in a different generation, but I think my father was confessional and he was also very concerned with his parents and his kids. He wrote about it in maybe a more conservative way than I do, but he was a very classy, stylish writer and at the bottom of his writing, the emotion is there.”

Wainwright has outlasted his progenitors and entered what he calls “chronologically my last years”, so it’s no surprise that his thoughts on the new record turn to weighing up his accomplishments. What is it, exactly, that he’s achieved with his lifetime? He tots it up on the album’s title track. “I mean, I won a Grammy whenever that was,” he says (2010, Best Traditional Folk Album for High Wide & Handsome: The Charlie Poole Project).“And I picked up a BBC [Radio 2 Folk Awards] Lifetime Achievement Award a few years back, but the hardware doesn’t really count. It always comes back to... What have you done with other people, your family and your loved ones?”

There are also the songs written. On “How Old is 75?”, longtime Wainwright fans will note lyrical references to a “swan dive” and “jack knife”, knowing nods back to one of his finest moments: 1973’s “The Swimming Song”. “That’s one of the songs I’m known for,” says Wainwright. “I still perform it. People still shout out for it. It’s been recorded more than any other, and used in a number of movies and television shows. It’s one of my important songs, so I don’t hesitate to reference it.”

Recorded in Nashville for Wainwright’s fourth album Attempted Mustache, “The Swimming Song” features not one but two banjos, enthusiastically strummed by Wainwright and the folk singer Kate McGarrigle. They married that same year and had two children, the musicians Rufus and Martha Wainwright, divorcing long before McGarrigle’s death in 2010. In the producer’s chair that day was Bob Johnston, a legendary figure from his work with the likes of Leonard Cohen and Bob Dylan. “He had done Blonde on Blonde and Nashville Skyline and John Wesley Harding,” recalls Wainwright. “So when Bob Johnston said, ‘I’d like to make a record with you’, I got pretty excited.”

From the start of his career in the late Sixties, Wainwright was considered one of a crop of potential “new Dylans”. The role had been vacant since 1966, when the folk icon went “missing in action” after crashing his Triumph T100 motorbike. “Labels, as they always do, went looking for, ‘Who can be the new Bob Dylan?’” recalls Wainwright. “Because I played the guitar, and was a guy, and wrote good songs, I was tagged as a ‘new Bob Dylan’, along with John Prine, Steve Forbert and even Bruce Springsteen. But, of course, Bob is the new Bob Dylan, and continues to be so!”

Among Wainwright’s early fans was influential Radio 1 DJ John Peel. “He played the s*** out of my first two records and singlehandedly created an audience for me in the UK in the Seventies,” says Wainwright, who will spend the next month touring Britain. “They’re now all in their seventies, but a lot of those folks still show up.”

Wainwright also made a fan out of country icon Johnny Cash, who recorded his song “The Man Who Couldn’t Cry” for 1994 comeback album American Recordings. “Wow, that was a thrill!” says Wainwright. “I went to see him perform at Carnegie Hall here in New York and got to meet him backstage. The version on the album was recorded live at the Viper Room, so there’s an audience there, and he gets some of the laughs. I told him, ‘Man you got it, because you got the laughs’. Johnny Cash recording ‘The Man Who Couldn’t Cry’, Mose Allison recording my song ‘I’m Alright’ and Earl Scruggs recording ‘The Swimming Song’ – those are real lifetime achievements.”

When the final curtain does come for Wainwright, you get the sense he’ll still try to squeeze in the last word. One of the sharpest and wittiest tracks on the new record is “Hell”, which sees Wainwright imagining a repeat offender returning to the realm of the damned only to get sucked into a softball game with Hitler, Pol Pot and Slobodan Milošević. How does Wainwright really see the afterlife panning out? “I wouldn’t characterise myself as a religious guy,” he says thoughtfully, turning to gaze at the trees outside his window. “But there’s something out there. I don’t know what the hell it is but it’s big, and it’s beautiful, and it has something to do with love.”

‘Lifetime Achievement’ by Loudon Wainwright III is out now on Proper Records. His UK tour begins in York on 7 September