March 22, 2023

The singer-songwriter fought with his father, fell out with children Rufus and Martha and drove away his first wife before the honeymoon was even over. At 76, has he finally made some kind of peace with the world?
Whisper it: Loudon Wainwright III is happy. The great curmudgeon of popular music has spent 50-plus years picking at old scabs, showcasing his selfishness and documenting his tortured relationship with his famous family. But he has finally made a hopeful album. Sure, we still hear from the Wainwright of old; the tragicomic misanthrope who quotes Sartre’s “Hell is other people” in the song Family Vacation, about his need to take a holiday from his family. But Lifetime Achievement shimmers with grace, acceptance and, dare we say it, love.
When I mention it, Wainwright sounds a little embarrassed. He ums and ahs, coughs and splutters his way to an admission of sorts. “Yes,” he says apologetically, “there are a number of songs that would make you wonder what’s happened here. It’s not the usual cynical nihilist that we’ve grown to love over the years. There is an optimism. The last few years have been good to me.”
Wainwright has dedicated the album to his partner, Susan Morrison, the New Yorker’s articles editor. Forget trophies and accolades, he sings on the gorgeous title track: “The biggest prize, the great surprise / Is I managed to win you.” Wainwright says he knew he was writing it for Morrison, but now realises it’s also for his audience.
What’s happened to the man who wrote One Man Guy, perhaps the supreme paean to numero uno? Well, he says, that song was more a statement of regret that he couldn’t connect with others than a celebration of self-love. “I think I always wanted to connect. We all want to connect. I don’t know what happened, but I’m just glad I feel less isolated.” He pauses, worried he’s sounding too euphoric. “Look, there are days I can still feel really isolated.”
He’s speaking by video call from the home he shares with Morrison on Long Island, New York. He’s 76 this week, and looks in great nick – strong arms, handsome face, mischievous twinkle. How old is Morrison, I ask. He calls down the stairs. “Hey Susan, he wants to know how old you are. I’m trying to remember. She’s much younger than me. She’s 62. I’m a cradle robber.” He laughs.
They’ve been together seven or eight years, he says. Is that a record for him? “It’s pretty good for me. I’ve never gone into double digits before, so we’re getting close.” Wainwright has been married twice, had numerous relationships and fathered four children with three women. All but one of the children are musicians – Rufus and Martha Wainwright are from his marriage to the Canadian singer-songwriter Kate McGarrigle; Lucy Wainwright Roche, also a singer, is his daughter from his relationship with Suzzy Roche; while Lexie Kelly Wainwright is his daughter with his second wife, Ritamarie Kelly. Families are complicated, as Wainwright tells me repeatedly – especially when you’ve got lots of them.
The refreshing thing about Wainwright is that nothing is off limits. Just as he has ruthlessly invaded his family’s privacy for inspiration, he expects others to do the same to him. When a question is deeply personal, he’ll tell you he shouldn’t go there, but can’t help himself. Wainwright is compulsively honest – which has served him brilliantly in his music career, less well in his private life. At times he has infuriated his children by mining their lives for source material. In recent years, Rufus and Martha have returned the compliment.
Wainwright, as his name suggests, comes from a mini-dynasty of Loudon Wainwrights. The first Loudon Wainwright was a wealthy entrepreneur. The money came from way back down the generations, Wainwright III explains. “There is a story of my grandfather and grandmother being in some swanky hotel in Europe on the day the stock market crashed in 1929 and my great-grandfather walked into the living room suite and said: ‘We’ve got to get the boat home – we’ve just lost $20m,’ or whatever they lost. A shitload of money.”
How had they made it? “They were investment bankers and robber barons, the usual way!” Did the money reach him? “No, it never got down to me or my dad’s generation. We grew up in a posh neighbourhood in Bedford, 40 miles north of New York City, and we were members of the golf club and the yacht club on Rhode Island, but my dad was making a journalist’s living. He didn’t have a lot of money, although we had cousins who were very rich.”
Loudon Wainwright Jr was a celebrated journalist – a columnist, reporter and interviewer for Life magazine. Wainwright says as far back as he can remember there was a rivalry between the two of them. In 2018, he made Surviving Twin, a Netflix film about their relationship. In the Freudian song of the same title, he sings about being mistaken for his father, and he answers that he is his father. Not only did they share the same name, his father sent him to the same school and gave him the same gold signet ring. They fought over the same woman (his mother), their level of fame and respective legacies. There were times that he was half-tempted to kill him, he sings, then asks: “How can you murder someone / In a way that they don’t die? / I didn’t want to kill him / That would be suicide.”
Did it upset him that he had the same name as his father? “It did. I didn’t like that at all. My dad was a famous journalist. I was the son of the Life magazine writer and I was really annoyed by it.” Who instigated the competition – his father or him? “I don’t know. I think every young person is competing with their parents. They have to at least equal them if not surpass them. So if you parent is famous, successful, that’s extra pressure.”
Does he feel he did out-succeed his father in the end? In a way, he says, but he doesn’t measure success as crudely as he used to. “I think I’m now more relaxed in the world than he ever was. He was a depressive guy, an alcoholic; his parents had been alcoholics. He smoked four packs of cigarettes a day. He got colon cancer when he was 59 and he died at 62. He was an unhappy guy.”
He pauses. “If he was sitting here, he’d be: ‘What are you talking about?’ After he died, I went to the gathering at the apartment and there were all these friends from his therapy and AA groups and they were all coming up to me and saying: ‘Your dad was the greatest, the warmest, he helped me,’ and I’m saying: ‘Who the hell are you talking about?’” He didn’t meet that man? “I met him very rarely. And that is very sad.” The Netflix film is his belated tribute to his father. He quotes from his writings, acts out his exquisite columns and sings about their relationship.
The young Wainwright III went to acting school in Pittsburgh but didn’t complete the course. Soon after he turned 20, he enlisted for the airborne division of the US army but overslept on the day he was due to enrol. When he woke up, he decided he had made a crazy choice and that the military wasn’t for him. He later managed to dodge the draft for Vietnam after his father’s psychiatrist wrote a letter saying he was a sociopath. Did the psychiatrist believe it? “I think I made him believe it. I was an actor. I was a little crazy for that 45 minutes.”
His first album, released in 1970, was simply called Loudon Wainwright III. From the off, his music was unpredictable – folk, country, jazz and rock were all there in the mix. Alongside the confessional stuff, there were any number of novelty songs – The Acid Song, The Swimming Song and his only hit, Dead Skunk, from 1972’s Album III. Despite the lack of commercial success, he had a strong cult following. Alongside Bruce Springsteen and John Prine, he was talked up as the new Bob Dylan. He took it seriously and stopped listening to Dylan because “it would be like being in a horse race and looking over at the other jockey”. When he realised it wasn’t going to happen, he wrote a song about failing to be the new Dylan.
Many of the early songs were about drink – Drinking Song, Down Drinking at the Bar, Central Square Song. Did he inherit his father and grandfather’s drink problem? “Well, I certainly drank too much when I was young.” He’s sipping from a flask of water as we talk. And now? “I don’t think I have a drink problem, no. I’ll have to ask Susan.” He bellows down the stairs: “Am I an alcoholic?”
“Naah!” she replies.
“We are both moderate people,” he says with a smile.
Actually, even back in the day, it was more complicated than simply drinking too much. Sure, he drank a lot, but he wanted to look as if he was drinking even more. It was all about image. “I would order a shot of Jack Daniel’s and a beer, but when people weren’t looking I’d pour some of the shot out because I didn’t want another hangover.” He was more calculating than he liked to let on.
His real problem, he says, was women. He couldn’t keep away from them. In 1971, he married McGarrigle. They split up in Copenhagen on their honeymoon. Wainwright couldn’t keep his eyes off the women of Denmark. Even today, he seems all of a tremble just thinking of them. “I was standing on the street corner looking at all the people. I mean, those people are crazy beautiful – men and women.”
Surely he didn’t sleep with somebody else on his honeymoon? “I was going to say, ‘Sadly no’, but I better not say that. I didn’t. But in my overly honest, stupid way, I conveyed my confliction to her about what I’d just done, which was get married. We had some huge screaming fight and she left.” He eventually found McGarrigle in London and they got back together, but it was always a troubled marriage. They separated five years later. “I was promiscuous, and that of course is murder on any marriage.”
You seemed a real shit back then, I say. He nods. “I was really behaving badly. I was a shit. In that marriage, I was out of control and shitty, yes. It kinda comes back to that thing of being famous. I had made a couple of records that got a lot of attention. I was happening and famous. You’re very powerful when you’re a big deal. You can sleep with anybody you want to and I did a lot of that. I guess it’s an addiction.” You were addicted to sex? “Yeah, at that time I was.”
When he and McGarrigle had children, Wainwright used them as source material for his music. He didn’t give it a second thought. Rufus Is a Tit Man is a celebration of his young son breastfeeding but also an expression of envy – that breast was meant for him, not Rufus, he sings: the least his son could do is share. Martha got the worst of it. Every parental failing was expressed in song. Hitting You is about the time he slapped Martha so hard his palm stung and how that led to the breakdown of their relationship. It’s a punishingly honest short story in song. I’d Rather Be Lonely appears to be about a failing relationship. “Let us make a brand new start / Separate and stay apart,” he sings. Martha was devastated when she discovered the song was about her and the year she spent living with her father.
Did he go too far in any of his songs? “There’s only one song I can put in that category.” Is it I’d Rather Be Lonely? “No. Martha has talked about that song. But I don’t regret writing or singing that song because, in my mind, it’s generic. It was inspired by the very difficult year we had when she came to live with me, but it’s about having a difficulty with anybody.”
So which song does he regret? “It’s called That Hospital. The song is about a hospital where I grew up. When Kate was pregnant with Martha, we went to that hospital to have an abortion procedure. At the end of the day, Kate did not have that abortion, but I reference it in the song. I would not sing that song now. It’s too personal, it crosses a line.”
Both Rufus and Martha have retaliated in song. Has he found their songs about him upsetting or educative? “Both. I think about them and sometimes they piss me off.” The kids or the songs? “Both!” Which songs? For once, he exercises something approaching caution. “Oh, I don’t want to get into particular songs on that count. Use your imagination, Simon!” I suggest Rufus’s song Dinner at Eight, which alludes to the time Rufus taunted his father about being featured in Rolling Stone for the first time in decades on the back of his son’s success, and Martha’s self-explanatory Bloody Mother Fucking Asshole.
He smiles. “Well, I like that first song a little better than the other one, let’s put it that way.” Does he think Martha’s song is unfair? “I don’t know. No, it’s about feelings. Write whatever you want to write about. It’s up to the songwriter.”
When I interviewed Rufus in 2007, he told me about the Rolling Stone incident: how Loudon went ballistic at his goading and threatened to kill him. Is that accurate? “Errr, that sounds right!” He laughs. “I don’t think I threatened to kill him, though. He was ascending and I was proud of it, but I was also like: ‘Hey, don’t forget this guy over here.’ People in show business are very insecure.”
Has all that rivalry disappeared now? “I don’t think it’s what it was. I doubt whether it’s totally eradicated. I think I’ve lightened up a little bit. God, let’s stop fighting here, let’s live a little!” Fighting is so sapping, I say. “Yes, it’s like unclenching a fist. If you walk around with a clenched first, eventually your stomach is going to seize up and clench, too.”
How is his relationship with Rufus and Martha these days? “It’s pretty good. Certainly better than it has been at times. And there’s grandchildren now, so we can focus on them.” Was there any reconciliation with McGarrigle before she died in 2010? He talks movingly about Rufus calling him when she was on her deathbed and asking if he would come to Montreal where she lived. “I got on a plane and I was in the house when she died, along with a lot of other family members. We couldn’t have had a conversation because she was so out of it, but I’m glad I was there.” Was she aware he was there? “I don’t know for sure. But I think it was important for Rufus that I was.”
Wainwright has been addressing the subject of death for decades. But it feels different on Lifetime Achievement. On How Old Is 75? he sings: “In five years I’ll be 80 / I will hear the fat lady”. It could be maudlin or fearful, but it’s a quietly serene song. That’s another way he’s getting less anxious, he says. “I write about being poised on a high diving board in this song. Maybe I’m more relaxed now because it’s almost time to jump.”
Loudon Wainwright III’s new album, Lifetime Achievement, is out now on Proper Records. He tours the UK from 7 September


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