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Stories I Might Regret Telling You by Martha Wainwright review – a hilariously candid memoir

You have to feel for singer-songwriter Martha Wainwright, whose memoir frames her as the least celebrated and – in her opinion – least desirable member of a revered musical family. Growing up in Montreal and New York, the younger of Kate McGarrigle and Loudon Wainwright III’s two children, she was given multiple reasons to doubt herself. Her mother told her she was “the definition of mediocrity”; her brother, Rufus, claimed he was McGarrigle’s favourite child; and her father, absent for much of her childhood, wrote a song directed at her. Titled I’d Rather Be Lonely, it detailed the ways she displeased him: “I think that I need some space / Every day you’re in my face / How can I get rid of you? / I’d rather be lonely.” (Martha later countered with Bloody Mother Fucking Asshole.) [https://www.youtube.com/watch?v=gbdsR5cDJlk ]

With that kind of raw material at her disposal, it’s remarkable that this isn’t another celebrity-tribulation story. Wainwright, though, isn’t that kind of celebrity. You’d struggle to call her a celebrity at all – despite abundant critical acclaim and a contacts book that includes Pete Townshend, Sean Lennon and Van Morrison (he was “a schmuck”, of which more below), she’s a steadfastly cult figure, albeit one connected enough to be able to casually note, “During [a recording session], Donald Fagen of Steely Dan dropped in to hear how things were progressing.”

Her refusal to be impressed by big names also provides one of the book’s funniest lines. Recounting the day the Police invited her mother and aunt to their studio, she laconically adds: “Or maybe it was Mark Knopfler, not the Police.” That conveys the tenor of her writing: acerbic, often hilarious and more candid than it should be. It’s easy to understand why she “might regret” telling some of these stories, especially those related to her rancorous 2018 divorce from producer Brad Albetta. But that’s Wainwright, and her transparency is the book’s golden ticket. Spoiler: there’s a mostly happy ending. She and her family learn to live with their differences, she finds love again, and her mother’s 2006 cancer diagnosis leads to greater kinship between them.

Wainwright continually compares herself with her more garlanded family and friends, undermining her confidence even further

Because she has never been a big name herself, Wainwright views her career as something of a failure, an undercurrent that throbs throughout the book, along with her incessant doubts about herself. She’s too loud, too brash, not pretty enough to attract the men she falls in love with, and she writes about it with flinty humour. (“I found it devastating that I was thought of as handsome, at best” is her appraisal of her looks.)

Coming from a famous clan and having seen success close up makes it all the harder. Wainwright believes in her music and loves performing, but continually compares herself with her more garlanded family and friends, undermining her confidence even further. “Though I was a ‘daughter-of’ twice over, doors seemed closed to me,” she writes, brooding that sons-of such as Sean Lennon and Chris Stills quickly got record deals and media attention while she had to slog for years. In the early stages of her career, an invaluable source of income was touring with Rufus as his support act, and selling her self-released EP at the gigs. Eventually, aged 28, she signed to a Canadian label and put out her self-titled debut album. Four more studio LPs have followed, most recently 2021’s post-divorce release Love Will Be Reborn.

Related: Rufus and Martha Wainwright: ‘When Mum died, we sewed ourselves together again’

To the initiated, she is one of a kind, greatly admired for her blood-letting autobiographical songs and adventurous one-offs, such as a live album of Edith Piaf numbers, sung in French. Before having children, she lived an indie dissolute life, with plenty of drugs, unfulfilling sex and dysfunction in the mix – she was the sort of hedonist whose close friend gave her “a lot of good blow” as a wedding present. And she doesn’t hesitate to call a schmuck a schmuck. Wainwright found Van Morrison so boorish backstage after she had opened a show for him, she couldn’t believe this was the same man who had made one of her favourite albums, Veedon Fleece. (It didn’t stop her loving the record.)

In short, she has had a life worth documenting. At the end of 244 remarkable pages, she signs off with a typically self-effacing line: “Perhaps I am someone whose luck gets better halfway through. That would be good.” It would be good, and she would deserve it.

• Stories I Might Regret Telling You by Martha Wainwright is published by Simon & Schuster (£20). To support the Guardian and Observer, order your copy at guardianbookshop.com. Delivery charges may apply.