Best American Novelists

Who will be knocked out and who will make it through to the next round? Photograph:

Introduction

Harper Lee produced only one, Ralph Ellison visibly poured everything he had into his raw gargantuan work, and JD Salinger seemed to be forever beholden to Holden. I want to find a persistent purveyor of Great American Novels; someone who hit them out of the park again and again. In short, the greatest US writer of the last 100 years. So I created a knockout tournament to find my winner.

Last time, in the opening matches, Faulkner, Proulx, Wharton, Hemingway, Doctorow, DeLillo, Updike and Steinbeck all penned their way into the next round. This time Saul Bellow, Raymond Chandler, Cormac McCarthy, John Fante, Toni Morrison, William Styron, Philip Roth, Richard Ford, Thomas Pynchon, Carson McCullers, Willa Cather, F Scott Fitzgerald, Sinclair Lewis and Wallace Stegner battle it out.

First up:

Herzog by Saul Bellow vs The Long Goodbye by Raymond Chandler

These two writers are as different as chalk and cheese. Bellow, the big cheese of American letters, has won three national book awards, the Pulitzer Prize and the Nobel Prize for literature. He has many notable literary acolytes including Amis, Roth and Bradbury and in this head to head he is up against that much maligned thing, a "genre" writer. A slam dunk, surely? Although Chandler is definitely the underdog – a term that typifies his main character, Philip Marlowe - it must be noted that Chandler not only stands (alongside Dashiel Hammett) at the pinnacle of American crime writing, but transcends the perceived limitations of a crime genre. For all their differences, and they are legion, both novels are built around a strong and colourful hero. This book battle could be waged as the battle of the characters - Moses Herzog versus Philip Marlowe.

Saul Bellow, Herzog (Penguin Modern Classics)

Herzog is a playful novel that follows the mental dissolution of the punctured professor, Moses Elkanah Herzog (the name taken from a minor character in Joyce's Ulysses and a nod to the meanderings of a troubled mind). His second wife Madeleine – the "devil-bitch" – has left him for his former best friend, the peg-legged, fox-haired Valentine Gersbach. His life is ruined and in order for him to cope with the litany of failures and tragedies and remain, on the surface at least, confident and cheerful, he submits to a mental fracture, the main symptom of which is endless writing:"To the newspapers, to people in public life, to friends and relatives and at last to the dead, his own obscure dead, and finally the famous dead."

This writing starts as brief notes and blossoms into full-blown essays that give Bellow a chance to display his philosophical chops. Herzog's mental meanderings are entertaining, amusing and insightful but eventually my enjoyment began to wane. At the start of the novel, I basked in the warm and wise writing and happily jotted down many great quotes, but they became just succulent berries in a dense, thorny bush of a novel. Mr Bellow, I can see that you are brilliant, but where is all this really getting us? "Knock off the crap, dreamy boy, " one of his detractors drawled at him, and I tend to agree. The inconsistencies of Herzog himself – a paunchy, balding man who attracts a cast of desirable women – seemed odd. He is a brilliant philosophy academic but the book is slow and it felt a little too contrived.

The Long Goodbye is the sixth Philip Marlowe novel and we find him as a 42-year-old veteran sleuth seemingly searching more for truth and humanity than for criminals. He likes "liquor and women and chess and a few other things". He is the enemy of insincerity, envy and greed, and oh yes, he doesn't do divorce cases. He takes more than his fair share of beatings and sleights to find his way to the solution, but the solution is clearly not Chandler's aim (he was famously irked by "plotting" and once said that a solution, once arrived at, should seem inevitable). The plot is complicated enough – there are suicides that could be murders and murders that could be suicides and Marlowe finds himself both investigating and investigated – but really it is about the characters. There is a fantastic cast of troubled souls, street toughs and corrupt cops and Chandler gives them all great depth. He imbues them with vibrancy and verve and leaves Marlowe, that astute professor of people, to dissect them for our pleasure.

Raymond Chandler, The Long Good-bye

I felt the poignancy and tragedy of Chandler's own alcoholism and artistic doubts throughout the book, particularly in the troubled writer Henry Wade. Marlowe gets himself entangled with the writer and his beautiful wife. Robert Altman cast Sterling Hayden as Wade in his 1973 film version, bearded and brooding, an apparent homage to Hemingway, and there is a feel of Papa in the whole tone of Chandler's novel.

There are diatribes on Blond's rather than Bellow's philosophical symposia, but Chandler can also riff marvellously on advertising, empty commercialism and the corruption of power. While Bellow is the intellectual superior, Chandler has more oomph and more humour. His writing, behind the entertaining, overblown descriptions and swaggering waggery, seems to come from a deeper level of his soul and therefore feels so much more enduring.

I really wanted to prefer Herzog, but as Mark Twain once wrote: "You can't reason with your heart; it has its own laws, and thumps about things which the intellect scorns." And my heart thumps for Chandler, more specifically for his great character, Marlowe. If high-falutin psychobabble and schadenfreude is your thing, well, as Marlowe said "You take it, friend. I'll take the big sordid dirty crooked city."