Male friendship, the way it works, the way people think about it, is going through a generational shift. To feel the change you just have to watch old movies. Last week, I made my kids sit through Diner, which I always thought of as one of my favourite films. It’s about a bunch of twentysomething guys in Baltimore in 1959, struggling to take the next step into adulthood. They argue about football and sandwiches, about Presley and Sinatra … but I’d forgotten how much they talk about sex, too. One of them bets he can “ball” a girl on a second date, another tells stories about the first time he “copped a feel”. Part of the point, of course, is that all this sexism is getting in the way of their lives. They don’t really know what to talk about with women, but the movie is also clearly nostalgic for their late-night bull sessions in the diner. All of which makes male friendship, and the way it mixes guilt and innocence, an interesting thing to write about.

One of the weirdest weekends of my life was when I flew out to Barcelona to interview LeBron James. After waiting around for two days, I was finally ushered into the large hotel room where he was doing media. Our interview, it turned out, was going to have an audience – which included not just agents, publicists and Nike reps but some of LeBron’s old high school teammates who now formed part of his entourage. I wondered what it was like to be one of the guys whose whole life had been shaped by someone he happened to play basketball with 10 years before.

Like the guys in Diner, were they trapped in a dynamic that really made sense only in high school? A few years later I started writing The Sidekick, about the complicated relationship between a sports reporter and an NBA player who grew up together. The reporter watches him change over time, from the kid he used to ride the bus with to someone who flies around on his own private jet. One of the things I realised in the course of writing the book is that friendship plots serve as a foil for all the other plots, in the same way that our friends’ successes give us something to compare our own to. It’s hard not to ask yourself after a while: what’s the difference between us that makes our lives so different? I thought we were pals, I thought we were basically the same …

Here then is a list of 10 great stories about male friendship, with all its problems and consolations.

1. The Three Musketeers by Alexandre Dumas
This was my favourite novel as a kid. I’ve never forgotten the terrible scene at the end when the four friends execute the treacherous Milady, Athos’s ex-wife and d’Artagnan’s former lover. Looking over that scene now, I am struck by how it reads today – a gang of men gathered to punish a woman, partly because of her power to “seduce” them. But you can also hear Dumas’ admiration for Milady, as she manages to slip her bonds and almost escape up the grassy slope by the river …

2. David Copperfield by Charles Dickens
This is a book about many things, but male friendship is certainly one of them until the romance plots and the bildungsroman take over. “Think of me at my best,” Steerforth says, a few nights before he runs off with Copperfield’s childhood sweetheart, Little Em’ly. Dealing with the sense of betrayal is part of what makes him grow up.

3. Brideshead Revisited by Evelyn Waugh
A reminder that you don’t fall just for people but also for the worlds they come from. At various points, Charles Ryder has to choose between Sebastian and his family, and even marries his best friend’s sister, but you always get the sense that their friendship lies deeper than all of the other storylines that grow out of it.

4. The Sun Also Rises by Ernest Hemingway
Not the happiest picture of male bonding. Robert Cohn beats up Jake Barnes over a woman, when really all the guys were just supposed to go fishing together. And yet when they do go fishing you feel their closeness: Bill and Jake compete over the daily catch, but in a friendly way, and words get picked up and bantered around between them – “Let us utilise the product of the vine” – until the outside world, with its more complicated relations, pulls them back in.

5. The Third Man by Graham Greene
It’s the EM Forster question: if you had to choose between betraying your country and your friend, which would you choose? And what if “your country” in this case stands for hospitals full of sick children made sicker by the watered-down penicillin your old school pal has been selling on the black market? One of those stories in which the lover turns out to be more faithful than the friend.

6. On the Road by Jack Kerouac
Beat writer Sal Paradise drives across America with his crazy old friend Dean Moriarty, getting drunk, getting laid, seeing the sights. There’s much in the novel that’s dated – including Dean’s treatment of women. Sometimes it’s hard to tell if he’s supposed to be the hero or the butt of the joke. But the book is also a reminder of what it was like to want to talk so much, to argue about the world, and to think of “experience” as the thing that would help you settle those arguments.

7. Lonesome Dove by Larry McMurtry
About the last days of the American West. The heroes are two Texas Rangers, Gus McCrae and Woodrow Call, and their friendship is at the heart of the story. What binds them is partly a shared competence, and partly a shared code. Though the two men are very different from each other, they trust and make use of those differences in a way that’s just as intimate as a conversation. When Gus dies, the world for Woodrow becomes a less interesting place to succeed in.

8. Sag Harbor by Colson Whitehead
The title comes from the beachfront neighbourhood in Long Island where African Americans settled after the war. It’s a coming-of-age story for a group of teenage boys, whose friendship is a form of competition. It forces them to work out a version of their identities that can pass the test of constant mockery – “as time went on, we learned to arm ourselves in our different ways”.

9. 1939 by Peter Taylor
Maybe my favourite short story. Two undergrads drive down from Kenyon College to meet their fiancees in New York. The young men want to be writers and care more about their futures than their friendship. But things don’t go well for them in the city. The car breaks down, their girlfriends dump them. On the train ride back to Ohio they get in a fight. Eventually the fight blows over, and by the end they’re just a couple of buddies heading back to college, who don’t yet have to face the rest of their lives.

10. Three Men in a Boat by Jerome K Jerome
One of the reasons friendship is hard to write is that the best friendships are often undramatic – people getting along, having a good time. Even if they get on your nerves, it doesn’t really matter because you can always make fun of them for it. This is one of the first books I read in lockdown, and my son used to listen to the Martin Jarvis recording on repeat. Comfort food, but it also seems pretty close to what ordinary friendship is often like.

• The Sidekick by Benjamin Markovits is published by Faber. To help the Guardian and Observer, order your copy from guardianbookshop.com. Delivery charges may apply.