The actor and comedian Robert Webb is seven years old when the penny drops about boys and their feelings. He is in his final year at infant school and is known for being quiet. “I wish they were all like you, Robert,” say the mums at birthday parties as the boys run noisily amok, while his mother tells his teachers, “He’s just a bit shy.” At the local golf club where his granddad works as a kitchen steward, Webb finds a bee on the gravel courtyard and, observing its laboured attempts at crawling, realises it is close to death. Rain is on its way so he builds a small circle of tiny stones around it for protection and, with tears in his eyes, leaves it to its fate.

“I’m not going to tell anyone about this, not even Nan or [Aunty] Tru or Mum,” he decides. “They would be nice about it, of course, but I know the truth about my bee. I wasn’t supposed to look after it. I was supposed to stamp on it.”

In this coming-of-age memoir, Webb, who was born in 1972, tells the story of his upbringing as the youngest son of a working-class woodcutter in the village of Woodhall Spa in Lincolnshire. He also examines, with enormous poignancy and insight, the damage that can be done when young boys are encouraged to behave in ways supposedly befitting their gender.

In the late 1970s, certain rules had to be observed for a boy to fit in. These included: not crying, not discussing feelings, not being gay, hating girls, getting into fights, obsessing about sport and, when the occasion demanded it, stamping on bees. None of these things came easily to Webb, who was sensitive, had sticky-out ribs, liked poetry and hated sport. During football lessons he would “welcome the sight of the ball arching towards me in the same way that a quadriplegic nudist covered in jam welcomes the sight of a hornet”.

Webb’s early portrait of himself as a hapless underdog navigating the boulder-strewn path of masculinity is vividly drawn and very funny. There are echoes of Adrian Mole in the way he seesaws between priggishness and melancholy (the young Webb also kept a diary). These years are rich in period detail, full of Anaglypta wallpaper, Raleigh bikes, Knight Rider, aniseed balls chain-smoking adults and singalongs to Rod Stewart’s “Sailing” in the car. His life, on paper, is close to idyllic, though, under the surface, anxiety, dread and confusion reside. Webb’s childhood was spent under the shadow of his father, Paul, who was admired in the village for his drinking and philandering, and feared at home for his explosive temper. For Webb and his two brothers, elbows on the tables would be dealt with by being “knocked clean from our chairs”. Once, while watching The Six Million Dollar Man, he recalls being lifted off his seat and thrashed around the legs with his own Woody Woodpecker-embroidered shorts. He never found out why.

There are echoes of Adrian Mole in the way Webb seesaws between priggishness and melancholy

Eventually Webb’s mother left, taking her sons with her. A year later she married Derek, the “teetotal and mild” owner of an agricultural spare parts company, with whom they found a degree of stability. But at 17, Webb’s life was upended again when his mum was diagnosed with breast cancer and died shortly afterwards.

It’s at this point, with his fate in the hands of two emotionally dysfunctional men, that his crisis began in earnest. What had started as self-doubt morphed into severe self-loathing that enveloped his years at Cambridge and his early forays into writing and acting, and manifested itself in arrogance, frequent drunkenness and treating his girlfriends badly.

While Webb milks his most atrocious moments for laughs – there’s the time when, talking to his mother on her deathbed, he moans about still being a virgin, while at college he cheats on his girlfriend with two women in one night – he treats the underlying problems that have afflicted him and scores of other men with the utmost seriousness. It’s to his credit that he never loses sight of his privilege as a man, and the cost of that privilege to women. If at times his fear of a feminist roasting is palpable – “feminists aren’t out to get us,” he explains, rather unnecessarily. “They are out to get the patriarchy. They don’t hate men, they hate The Man” – he is clear and convincing in his argument that addressing the gender conditioning of men will improve life for all.

It’s with a mixture of bafflement and frustration that he unpicks the semantics of masculinity and femininity, noting how many words “come pre-loaded with a steam tanker of gender manure from the last century”. He asks what it is to “act like a man”, why men struggle to maintain adult friendships and why they are more likely than women to kill themselves. “To put it childishly,” he says, “if you want a vision of masculinity, imagine Dr Frankenstein being constantly bum-raped by his own monster while shouting, “I’m fine, everyone! I’m absolutely fine!”

These, then, are the themes that underpin Webb’s memoir, and are the prism through which he views his own life. Caitlin Moran’s How to Be a Woman is referenced here in the title and the cover image, but this is less a righteous manifesto for the modern man than a highly personal story that might just resonate with others and give them confidence to talk, too.

“Being male is terrific,” Webb says, “but comes with an extra load of baggage that is worth noticing. Because you might be carrying a load of stuff you don’t need. Stuff which is getting in your own – and other people’s – way.”

• How Not to Be a Boy is published by Canongate. To order a copy for £12.74 (RRP £16.99) go to bookshop.theguardian.com or call 0330 333 6846. Free UK p&p over £10, online orders only. Phone orders min p&p of £1.99.