Emma Brockes on Goodbye, Columbus (1959)

I fell in love with Neil Klugman, forerunner to Portnoy and hero of Goodbye, Columbus, Philip Roth’s first novel, in my early 20s – 40 years after the novel was written. Descriptions of Roth’s writing often err towards violence; he is savagely funny, bitingly honest, filled with rage and thwarted desire. But although his first novel rehearses all the themes he would spend 60 years mining – sexual vanity, lower-middle-class consciousness (“for an instant Brenda reminded me of the pug-nosed little bastards from Montclair”), the crushing weight of family and, of course, American Jewish identity – what I loved about his first novel was its tenderness.

Goodbye, Columbus is steeped in the nostalgia only available to a 26-year-old man writing of himself in his earlier 20s, a greater psychological leap perhaps than between decades as they pass in later life. Neil is smart, inadequate, needy, competitive. He longs for Brenda and fears her rejection, tempering his desire with pre-emptive attack. All the things one recognises and does.

My mother told me that the first time she read Portnoy’s Complaint she wept and, at the time, I couldn’t understand why. It’s not a sad novel. But, of course, as I got older I understood. One cries not because it is sad but because it is true, and no matter how funny he is, reading Roth always leaves one a little devastated.

I picked up Goodbye, Columbus this morning and went back to Aunt Gladys, one of the most put-upon women in fiction, who didn’t serve pepper in her household because she had heard it was not absorbed by the body, and – the perfect Rothian line, wry, affectionate, with a nod to the infinite – “it was disturbing to Aunt Gladys to think that anything she served might pass through a gullet, stomach and bowel just for the pleasure of the trip”. How we’ll miss him.

Emma Brockes is a novelist and Guardian columnist

James Schamus on Goodbye, Columbus (1959)

Philip Roth was more than capable of the kind of formal patterning and closure that preoccupied the work of Henry James, with whom he now stands shoulder-to-shoulder in the American literary firmament. So yes, one can always choose a singular favourite – mine is the early story Goodbye, Columbus, though I know the capacious greatness of American Pastoral probably warrants favourite status. But celebrating a single Roth piece poses its own challenges, in that his life’s work was a kind of never-ending battle against the idea that the great work of fiction was anything but, well, work – work as action, creation; work not as noun but as verb; work as glorious as the glove-making so lovingly described in Pastoral, and as ludicrous as the fevered toil of imagination that subtends the masturbatory repetitions of Portnoy’s Complaint. Factual human beings are fiction workers – it’s the only way they can make actual sense of themselves and the people around them, by, as Roth put it in Pastoral, always “getting them wrong” – and Roth was to be among the most dedicated of all wrong-getters, his life’s work thus paradoxically a fight against the formal closure that gave shape to the many masterpieces he wrote. Hence the spillage of self, of characters real and imagined, of characters really imagining and of selves fictionally enacting, from work to work to work. So, here, Philip Roth, is to a job well done.

James Schamus is a film-maker who directed an adaptation of Indignation in 2016

Peter Bradshaw on Portnoy’s Complaint (1969)

I read it when I was about 18 – an off-piste literary choice in my sobersided studenty world. I had been earnestly dealing with the Cambridge English Faculty reading list and picked up Portnoy having frowned my way through George Eliot’s Romola. The bravura monologue of Alex Portnoy wasn’t just the most outrageously, continuously funny thing I had ever read; it was the nearest thing a novel has come to making me feel very drunk.

And this world-famously Jewish book spoke intensely to my timid home counties Wasp inexperience because, with magnificent candour, it crashed into the one and only subject – which Casanova, talking about sex, called the “subject of subjects” – jerking off. The description of everyone in the audience, young and old, wanking at a burlesque show, including an old man masturbating into his hat (“Ven der putz shteht! Ven der putz shteht! Into the hat that he wears on his head!”) was just mind-boggling. A vision of hell that was also insanely funny. Then there is his agonised epiphany at understanding the word longing in his thwarted desire for a blonde “shikse”. (Was I, a Wasp reader, entitled to admit I shared that stricken swoon of yearning? Only it was a Jewish girl I was in love with.) Portnoy’s Complaint had me in a cross between a chokehold and a tender embrace: this is what a great book does.

Peter Bradshaw is the Guardian’s film critic

William Boyd on Zuckerman Unbound (1981)

Looking back at Philip Roth’s long bibliography, I realise I’m a true fan of early- and middle-Roth. I read everything that appeared from Goodbye, Columbus (I was led to Roth by the excellent film) but then kind of fell by the wayside in the mid 1980s with The Counterlife. As with Anthony Burgess and John Updike, Roth’s astonishing prolixity exhausted even his most loyal readers.

But I always loved the Zuckerman novels, in which “Nathan Zuckerman” leads a parallel existence to that of his creator. Zuckerman Unbound (1981) is the second in the sequence, following The Ghost Writer, and provides a terrifying analysis of what it must have been like for Roth to deal with the overwhelming fame and hysterical contumely that Portnoy’s Complaint provoked, as well as looking at the famous Quiz Show scandals of the 1950s. Zuckerman’s “obscene” novel is called Carnovsky, but the disguise is flimsy. Zuckerman is Roth by any other name, despite the author’s regular denials and prevarications.

Maybe, in the end, the Zuckerman novels are novels for writers, or for readers who dream of being writers. They are very funny and very true and they join a rich genre of writers’ alter ego novels. Anthony Burgess’s Enderby, Updike’s Bech, Fernando Pessoa’s Bernardo Soares, Ernest Hemingway’s Nick Adams, Edward St Aubyn’s Patrick Melrose and so on – the list is surprisingly long. One of the secret joys of writing fictionally is writing about yourself through the lens of fiction. Not every writer does it, but I bet you every writer yearns to. And Roth did it, possibly more thoroughly than anyone else – hence the enduring allure of the Zuckerman novels. Is this what Roth really felt and did – or is it a fiction? Zuckerman remains endlessly tantalising.

William Boyd is a novelist and screenwriter

Roth outside the Hebrew school he probably attended as a boy. Photograph: Bob Peterson/Time Life Pictures/Getty Images

David Baddiel on Sabbath’s Theater (1995)

Philip Roth is not my favourite writer; that would be John Updike. However, sometimes, on the back of Updike’s – and many other literary giants – books, one reads the word “funny”. In fact, often the words “hilarious”, “rip-roaring”, “hysterical”. This is never true. The only writer in the entire canon of very, very high literature – I’m talking should’ve-got-the-Nobel-prize high - who is properly funny, laugh-out-loud funny, Peep Show funny, is Philip Roth.

As such my choice should perhaps be Portnoy’s Complaint, his most stand-uppy comic rant, which is gut-bustingly funny, even if you might never eat liver again. However – and not just because someone else will already have chosen that – I’m going for Sabbath’s Theater, his crazed outpouring on behalf of addled puppeteer Mickey Sabbath, an old man in mainly sexual mourning for his mistress Drenka, which could anyway be titled Portnoy’s Still Complaining But Now With Added Mortality. It has the same turbocharged furious-with-life comic energy as Portnoy, but a three-decades-older Roth has no choice now but to mix in, with his usual obsessions of sex and Jewishness, death: and as such it becomes – even as we watch, appalled, as Mickey masturbates on Drenka’s grave - his raging-against-the-dying-of-the-light masterpiece.

David Baddiel is a writer and comedian

Hadley Freeman on American Pastoral (1997)

American Pastoral bagged the Pulitzer – at last – for Philip Roth, but it is not, I suspect, his best-loved book with readers. Aside from his usual alter ego Nathan Zuckerman, the characters themselves aren’t as memorable as in, say, Portnoy’s Complaint, or even Sabbath’s Theater, which Roth wrote two years earlier. And yet, of all his books, American Pastoral probably lays the strongest claim that Roth was the great novelist of modern America.

Zuckerman, who is now living somewhere in the countryside, his body decaying in front of him, remembers a friend from high school, Seymour Levov, known as “the Swede”, who seemed to have everything: perfect body, perfect soul, perfect family. But then the Swede’s life is shattered when his daughter, Merry, literally blows up all of her father’s dreams, by setting off a bomb during the Vietnam protests and killing someone. The postwar generation has rejected all that their parents built for them, and while Roth uses the Levov families as symbols for America’s turmoil, they are far more subtly realised than that. And in a terrible way, now that school shootings – almost invariably done by young people – are an all-too-common occurrence in America, the bafflement the Swede feels about Merry seems all too relevant. “You wanted Miss America? Well, you’ve got her, with a vengeance, she’s your daughter!” the Swede’s brother famously shouts at him. In today’s America, more divided and gun-strewn than ever, it’s a line that still chills.

Hadley Freeman is an author and Guardian columnist

Hannah Beckerman on American Pastoral (1997)

By the time I read American Pastoral I was a 22-year-old diehard Roth fan. But no book of his that I had read previously – not the black humour of Portnoy’s Complaint, nor the blistering rage of Sabbath’s Theater – had prepared me for this raw and visceral dismantling of the American dream. With Seymour “Swede” Levov – legendary high school baseball player and inheritor of his father’s profitable glove factory – Roth presents us with the classic all-American hero, before unpicking his life, stitch by painful stitch. Swede’s relationship with his teenage daughter, Merry – once the apple of his eye, now an anti-Vietnam revolutionary who detonates Swede’s comfortable life – is undoubtedly one of the most powerful portrayals of father-daughter relationships anywhere in literature. But this is Roth, and his lens is never satisfied looking in a single direction. Through the downfall of Swede Levov, Roth portrays the effects of the grand narratives of history on the individual, and questions our notions of identity, family, ambition, nostalgia and love. Muscular and impassioned, American Pastoral oscillates seamlessly between rage and regret, all in Roth’s incisive, fearless prose. It is not just Roth’s best book: it is one of the finest American novels of the 20th century.

Hannah Beckerman is a novelist, journalist and producer of the BBC documentary Philip Roth’s America.

Roth in 1977. Photograph: Alamy Stock Photo

Xan Brooks on I Married a Communist (1998)

Great novels hit you differently each time you revisit them, but a second reading of I Married a Communist felt like being flattened by a steamroller. For decades I had cast this as the brawling bantamweight of Roth’s American trilogy; bookended by the more polished American Pastoral and The Human Stain, and bent out of shape by the author’s personal animus towards ex-wife Claire Bloom (thinly veiled as Eve Frame, a self-loathing Jewish actor). These days, I think it may well be his best.

I Married a Communist charts the rise and fall of Ira Ringold, a leftist radio star who finds himself broken on the wheel of the 1950s red scare. Fuelled by righteous fury, it’s one of the great political novels of our age; a card-carrying Shakespearean tragedy with New Jersey dirt beneath its fingernails. And while the tale is primarily set during the McCarthy era, it tellingly bows out with a nightmarish account of Nixon’s 1994 funeral in which all the old monsters have been remade as respected elder statesmen. “And had Ira been alive to hear them, he would have gone nuts all over again at the world getting everything wrong.”

Xan Brooks is a novelist and journalist

Arifa Akbar on The Human Stain (2000)

I read The Human Stain when it was published in 2000. I was in a book club comprised of gender studies academics, gay women, women of colour. No men allowed. We had been reading bell hooks, Jamaica Kincaid and along came Philip Roth. I expected it to be savaged. I expected to do the savaging, having never read Roth before, precisely because of his much-disputed misogyny.

Then I read it, this tender, shocking and incendiary story on the failure of the American dream refracted through the prism of race, blackness and the alleged racism of Coleman Silk, a 71-year-old classics professor who embarks on an affair with a cleaner half his age, as if by way of consolation.

Here we go, I thought, and raised an eyebrow when she danced for this priapic old fool. But The Human Stain is much more than that single scene. Here was a Jewish American writer, taking on black American masculinity, filling it with its legacy of oppression, the perniciousness of the internalised white gaze, the “shame” that Silk feels that leads him to his lifetime’s masquerade. In less masterful hands, it could have read as dreadful appropriation.

I have re-read it since and it feels just as contemporary, like all great works of literature. It sums up so much about desire and ageing, but also institutionalised racism, the dangers of political correctness and colourism that we are increasingly talking about again.

Yes, we spoke of that dancing scene at our book club, but forgave it. There is something profoundly honest in the sexual dynamic between The Human Stain’s lovers. Roth caught male desire so viscerally and entwined it within the nexus of vulnerability, fear and the fragile male ego. I read the other Nathan Zuckerman novels afterwards and realised that you don’t go to Roth to explore female desire, but you read him for so much else.

Arifa Akbar is a critic and journalist

Jonathan Freedland on The Plot Against America (2004)

Rarely can a four-word note scribbled in the margin have born such precious fruit. In the early 2000s, Roth read an account of the Republican convention of 1940, where there had been talk of drafting in a celebrity non-politician – the superstar aviator and avowed isolationist Charles Lindbergh – to be the party’s presidential nominee. “What if they had?” Roth asked himself. The result was The Plot Against America, a novel that imagined Lindbergh in the White House, ousting Franklin Roosevelt by promising to keep the US out of the European war with Hitler and to put “America First”.

The result is a polite and gradual slide into an authentic American fascism, as observed by the narrator “Philip Roth”, then a nine-year-old boy who watches as his suburban Jewish New Jersey family is shattered by an upending of everything they believed they could take for granted about their country.

The book is riveting – perhaps the closest Roth wrote to a page-turning political thriller – but also haunting. Long after I read it, I can still feel the anguish of the Roth family as they travel as tourists to Washington, DC and feel the chill of their fellow citizens; eventually they are turned away from the hotel where they had booked a room, clearly – if not explicitly – because they are Jews. Like Margaret Atwood’s Gilead, the America of this novel stays in the mind because of the plausible, bureaucratic detail. Philip’s older brother is packed off to Kentucky under a programme known as Homestead 42, run by “the Office of American Absorption”, whose mission is to smooth off the Jews’ supposed rough edges, so that they might dissolve into the American mainstream, or perhaps disappear altogether.

It is not a perfect novel. The final stretch becomes tangled in a rush of frenetic speculations and imaginings. But it has an enduring power, which helps explain why the election of Donald Trump – who has often repeated, without irony or even apparent awareness, the slogan “America First” – had readers turning back to The Plot Against America, to reflect on how a celebrity president blessed with a mastery of the modern media might turn on a marginalised minority to cement his bond with the American heartland. Nearly 70 years after Sinclair Lewis’s It Can’t Happen Here, Roth insisted that it could – and he detailed precisely how it would feel if it did.

Jonathan Freedland is an author and a Guardian columnist

Roth in New York City. Photograph: Orjan F. Ellingvag#51SY ED/Getty Images

Linda Grant on Nemesis (2010)

After Philip Roth published The Plot Against America in 2004 and came to the end of the great sequence of long, state-of-the-USA novels beginning with Sabbath’s Theater, which were his brilliant, late, but not last period, he published a number of short novels that felt like a coda to the main body of work. They centred round the ageing, dying male, the declining libido, old age all alone. Then, with a final surprising flick of his fingers, he wrote Nemesis, returning to his youth in postwar Jewish Newark where it all starts. He uncovered one last story, the forgotten epidemic of polio that affected mainly children and young adults and whose malevolent transmission was the subject of conspiracy theories, a population blaming, as ever, the Jews.

It is the story of aspiring heroes and their moral failure, the lifelong consequences of striving to do the right thing and disastrously doing something so wrong you become trapped in a carapace of guilt. With his protagonist Bucky Cantor, Roth encapsulates his fascination with the heroic generation of Jewish kids destined for great things, and the ones who failed. Though I’ve read all of Roth, it’s the novel I’m most likely to recommend to absolute beginners to his work. It’s him in miniature, yet perfectly whole.

Linda Grant is a novelist

Alex Ross Perry on The Professor of Desire (1977)

I discovered the novels of Philip Roth as I have most literature during my 15 years in New York: on the subway. The experience of pouring over the sexual nuance of The Professor of Desire while surrounded by children and the elderly created a perplexing dichotomy between brown paper bag smut and totemic American fiction. This was both transformative and inspiring, illuminating for me the possibility of couching perversion, sexuality, anger and humour into a piece of work rightly perceived as serious and intellectual. Each transgressive element became less shocking as I made my way through Roth’s novels on F trains and Q trains, the feelings of shock replaced with the intended understanding of what these “amoral” acts said about the characters and the novels they inhabited.

I’m not sure if I would call The Professor of Desire my favorite of Roth’s novels (an honor I generally bestow upon Sabbath’s Theater, which I have learned seems to be the low key favourite of those in the know) but it was certainly the first to announce itself to me as massively influential. The Kepesh books introduced me to a view of improper, quasi-abusive relationships within academia that gave me the professor character in my film The Color Wheel.

When I began writing The Color Wheel in 2010, Roth was my north star. I intended to reverse engineer a narrative with the same youthful arrogance flaunting sexual taboos that excited, then inspired, me in his work. Depicting the story of an incestuous sibling relationship, but presenting it in the guise of a black and white independent art film, felt like a genuine way to honor the work of this titan; those books bound in the finest jacket design the twentieth century had to offer, elegantly concealing without so much as a hint the delightful perversions contained within.

Alex Ross Perry is an actor and filmmaker

Amy Rigby on The Ghost Writer

I refuse to accept the assertion that misogyny in Philip Roth’s novels makes it impossible for a woman to find herself in his characters. I want to - have a right to - identify with the great man or the schmuck.

I started reading The Ghost Writer looking for a road map to a stunning middle-career but found myself in a house of mirrors. The 46-year-old author looks back at himself as an accomplished beginner who visits an older giant of letters. Parents, wives, lovers - even Anne Frank - weigh in. It’s funny and moving and compact.

I picked it up again today, touched that anyone would ask for my thoughts on this genius whose work ethic and output made his greatness undeniable, whether you believe in him or not, and found this passage contained in Judge Wapter’s letter to young Nathan Zuckerman, who recounts it to us with such scorn and hope I couldn’t help but feel like a schmuck myself, or at least a poser: “I would like to think that if and when the day should dawn that you receive your invitation to Stockholm to accept a Nobel Prize, we will have had some small share in awakening your conscience to the responsibilities of your calling.’” You really were robbed, Phil.

Amy Rigby is a singer and songwriter. Her songs include From Philip Roth to R Zimmerman

Joyce Carol Oates on Roth’s legacy

Philip Roth was a slightly older contemporary of mine. We had come of age in more or less the same repressive 50s era in America – formalist, ironic, “Jamesian”, a time of literary indirection and understatement, above all impersonality – as the high priest TS Eliot had preached: “Poetry is an escape from personality.”

Boldly, brilliantly, at times furiously, and with an unsparing sense of the ridiculous, Philip repudiated all that. He did revere Kafka – but Lenny Bruce as well. (In fact, the essential Roth is just that anomaly: Kafka riotously interpreted by Bruce.) But there was much more to Philip than furious rebellion. For at heart he was a true moralist, fired to root out hypocrisy and mendacity in public life as well as private. Few saw The Plot Against America as actual prophecy, but here we are. He will abide.

Joyce Carol Oates is a novelist