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Robert Webb’s biography serves as a primer for what a modern man should – and shouldn’t – be.

In the ninth and final season of the British sitcom Peep Show, the perpetually listless, sexually voracious, fully adult man-child Jeremy (Jez) Usborne, played by comedian Robert Webb, is tapped to deliver a last-second speech at a friend’s wedding. Lacking any prepared remarks, Webb’s Jeremy launches into a free-form reflection on love, sexuality, gender and polyamory, working through his own romantic predicaments in front of a profoundly confused audience.

“If someone loves someone, he just loves them,” he begins, before rambling well outside the perimeter of comprehensibility. “Why is a marriage a marriage but society says it’s wrong for two men to love one another, even though, now, it says it says that now it’s okay? Is it okay because society says it’s okay? What next? Dogs getting married? Could I marry my own son? No. Possibly not? Correct. Or is it? What I’m trying to say is…”

This sense of utter bafflement is at the heart of Webb’s new memoir-cum-manifesto, How Not To Be A Boy. The story of a young, funny, maladjusted lad growing up in central England, Webb’s life story is shot through with vital reflections on contemporary masculinity and the oldfangled social expectations that still dog men and boys. Both deeply personal and bracingly timely, Webb’s biography serves as a primer for what a modern man should – and shouldn’t – be.

“I’ve always had this preoccupation with gender and masculinity,” Webb explains, over the phone from Brisbane, Australia, where he’s promoting the book. “It starts in childhood. It has to do with the way boys are raised. If you fall over and graze your knee, and want to cry, you know for some reason – from a thousand cues, not unkindly meant – that you’re not supposed to cry. That’s not what boys do. The suppression of any negative emotions is connected with the inability to talk.”

A renowned comedian, actor and editorialist in his native Britain, who never seems especially short on words, Webb first learned to talk – like, really talk – when he was in high school, and lost his mother to breast cancer. “When my mom died, I was surrounded by all these lovely people who said they were there if I wanted to talk. That was novel,” he recalls. “All of a sudden, they want me to talk? How does that help?’”

How Not To Be A Boy follows Webb’s coiled, conditioned repression: from his fumbled attempts to woo the opposite sex to his standoffish interactions with his alcoholic and emotionally distant father, to his own struggles with booze and self-worth. It is at once intimate and funny, approaches Webb feels are invaluable in communicating with his target audience. How Not To Be A Boy constitutes, as Webb puts it, in a perfectly English turn of phrase, a sustained effort to “get through to blokes.”

“You can say serious things in a light way, and it slips under the radar,” he says. “I don’t want them to feel like I’m giving them a lecture. That will just bounce off their pride. I know what they’re like. I am one.”

Webb’s interest in masculinity and what he calls “gender conditioning” feels purposefully of the moment. Ours is an age when matters of patriarchy, gender roles and the place of men in society feel front and centre. Much of this discussion is marred by regressive thought and reaction, by so-called “incels,” men’s rights activists and Proud Boys flailing to restore the order of masculine dominance. For Webb, some of the concerns shared by such groups are valid. It’s the approach that needs rethinking.

“Men in trouble,” Webb writes, “are often in trouble precisely because they are trying to Get A Grip and Act Like a Man. We are at risk for suicide because the alternative is to ask for help, something we have been repeatedly told is unmanly. We are in prison because the traditional breadwinning expectations can’t be met.”

If there’s a point Webb wants to drive home, it’s that the patriarchy doesn’t just fail women or minority groups. It fails the very men it endeavours to prop up. In his book, he uses, as an analogy for masculinity, a rather colourful, un-reprintable image of a mad scientist being brutally assaulted by his Frankenstein creation, all the while insisting that nothing’s the matter.

Although he doesn’t mention them by name in the book, Webb has particular disdain for charlatans endeavouring to renormalize age-old, utterly arbitrary social hierarchies. In advance of our interview, the publicist warns me not to ask him about such a figure: Toronto clinical psychologist turned touring carnival barker Jordan Peterson. But it’s not long before Webb brings him up, as if inevitably.

“He talks about ‘enforced monogamy,’” says Webb, citing a recent New York Times profile of Peterson. “It’s repulsive. I can’t imagine a more grotesque idea. And there’s nothing new about this. It’s just satisfying the needs of men, and blaming women. I find the whole thing incredible. This vain, stupid old man is given such credence.”

Webb’s worry – shared by many – is that Peterson’s free-ranging mishmash of psychology, evolutionary biology, philosophy, mythology and fatal misreadings of George Orwell offers the modern masculinist movement an illusion of intellectual heft it doesn’t deserve.The guy’s a joke,” Webb sneers. “If he weren’t so dangerous, he’d be laughable.”

The august Austrian critic and satirist Karl Kraus once attacked the then-emerging soft science of psychoanalysis, describing it as the very disease it purports to cure. The same can be said of Peterson, Proud Boys and other contemporaries whose thinking on masculinity is demonstrably conservative. Webb’s approach offers something closer to a workable solution – or at least a solid diagnosis.

He is sensitive to the widespread, invisible ideological structures that condition individuals in society. And he provides sharp, funny insights that go a long way to laying their operations bare. “We think that gender conditioning is something that happens to girls, and gay people, and trans people,” he says. “But no! It happens to us. Men find it easy to forget because we’re given the strong impression that we’re the default human. You go into a gent’s loo and it’s the outline of a human being. You go to the women’s loo and it’s the outline of a human being in a skirt. It’s human plus difference.”

He’s also aware that, as a man, he has a special privilege in addressing these issues. And also that such sustained conversations of masculinity undertaken can unfold at the expense of more marginalized voices. As he puts it, if a woman were to make the same claims in such a book, she’d be afforded “half the attention and three times the grief.”

Yet it is precisely because he’s a man that Webb feels a certain responsibility. In conversation, and throughout How Not To Be A Boy, Webb offers a thoughtful and deeply funny rethinking of the pressing question of what makes a man. He doesn’t believe that men should necessarily stop drinking beer or watching soccer. And it’s not like he expects men to tap into similarly conditioned, arbitrary notions of femininity. “I’m not saying that men should be bursting into tears every five minutes,” he says. “That would be horrible.”

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