What books make the best movies?

The movies have been stealing from novels ever since movies began, and for just as long the debate has raged: What books make for the best thefts? Well, the question is tired by now and maybe wrong too, but let's quickly answer it: easy comic books these days, along with anything scribbled by J.K. Rowling and her ilk – successful commercial writing lends itself to successful commercial pix, since both dance to the same populist beat. That's simple to figure. Far harder is the enduring, almost touching, efforts of the cinema to adapt accomplished literary fiction, clinging to the faith that a good novel can always be wrangled, not mangled, into a good film.

Even a cursory peek at the TIFF program suggests just how deep and abiding that faith remains. Great Expectations, Anna Karenina, What Maisie Knew, Midnight's Children, Cloud Atlas – all are born from great books and all rank among the most anticipated offerings at the festival. Yet a closer look reveals something much more intriguing: a pervading irony in the history of the print-flick relationship. First, the thievery has always been a two-way street. As soon as the chance arose, novelists swiped from the movies too, but with an ironic difference: What they stole tended only to widen the gap between the page and screen. In fact, weirdly enough, what they stole from film often made their own books unfilmable. Let's trace the chronology.

Great Expectations

He toiled before the dawn of cinema but, hands down, Charles Dickens is filmdom's perfect writer. Ol' Chuck could walk into any Hollywood pitch meeting today and talk the talk: "Hey, I got plot, a lotta plot; I got those funny flat characters that hammy actors love to play; and I got cliff-hanging narrative arcs galore 'cause, you know, I wrote the stuff in serialized instalments." Of course, his Regency predecessor, Jane Austen, could make an equally enticing pitch: "I write the most wonderfully witty dialogue, gentlemen, and a marriage plot never grows old." Poor Charlotte Bronte, who tiptoed around her weakness with dialogue by playing to her strengths – Gothic imagery and Byronesque brooding – isn't so lucky. The camera tends to over-literalize her prose, until all that brooding morphs into just-too-damn-heavy.

Anna Karenina

That earnest Count Tolstoy is a tougher nut to crack cinematically. Sure, Anna Karenina's famous first line – "All happy families are alike but an unhappy family is unhappy after its own fashion" – could double as a synopsis of every fourth movie ever made. And the novel itself has had umpteen adaptations, most notably with Greta Garbo herself. Yet film has big trouble disinterring from the page the complexity of our adulterous heroine, getting the right balance between her responsibility and her victimhood. It has the same problem with Flaubert's Madame Bovary. Apparently, in this version of Tolstoy's classic, director Joe Wright literally stages the action, almost as if he's trying to ease the transition into film with a stopover at the theatre. Might work.

What Maisie Knew

With Henry James, especially later James, the novel began its trek into modern psychological terrain. The movies have paid the Master much reverence, but their relationship has been strained, with the novels often reduced to Merchant/Ivory costume dramas (The GoldenBowl), or Olivia de Havilland's hysterics (The Heiress), or, risibly, to Jane Campion's feminist lacquer (The Portrait of a Lady). Maisie is his most technical novel, a tale of divorce observed and told exclusively from the limited perspective of the warring couple's young child. This literary gimmick is absolutely crucial to the book's success – good luck putting a lens to it.

Of course, in every James adaptation, what's gone are the psychological nuances embedded in, and inextricable from, his crystalline prose. In short, what's missing is the very signature of the modern novel – the writer's unique and intrinsic voice.

Now comes that really strange irony. The advent in the twenties of the great modernist writers coincided with the rise of film. Indeed, James Joyce, Virginia Woolf, William Faulkner (who briefly toiled in Tinseltown) were all intrigued by the movies, particularly by the narrative fluency of montage. And so they borrowed from film: Their stream-of-consciousness narration is a verbal mimicry of montage, only with the setting shifted from exterior to interior. But the more these modernists inserted filmic devices into literature, the more their literature became impossible to film. With the exception of John Huston's treatment of The Dead, James Joyce and the movies are a marriage made in hell. Ditto for Woolf and Faulkner – not a decent picture has sprung from anything they ever wrote. Each has a voice so strong that, without it, the film robs the book of its essence and leaves only what's least interesting – the plot.

Midnight's Children, Cloud Atlas

Here, literature has entered its magic-realist phase. Translation: With their sweeping time frames, shifting locales and blending of the real with the surreal, both these books are hugely cinematic and, as such, would seem to cry out for the camera. Yet, again, that return journey is typically doomed. Consider the works of magic realism's most celebrated proponent, Gabriel Garcia Marquez – every film made from his books is an all-out stinker. So the track record isn't good. Undaunted, Salman Rushdie tackled the screenplay himself for Midnight's Children, while David Mitchell, absenting himself from Cloud Atlas, trusted that higher math – not one but three directors plus 163 minutes of running time – might do the trick. Here's hoping.

A final note, touching on two writers I never thought I'd mention in the same sentence: David Foster Wallace and

Sheila Heti. Despite massive differences in intellect, substance and technique, their work does share the same intense interest in the way we live now, immersed within a visual culture hot-wired for alluring pop entertainments. And yet, even though deeply rooted in that culture, DFW's masterpiece, Infinite Jest, is completely unfilmable. So is Heti's How Should a Person Be? which, in its querying title if nothing else, owes more to the 16th-century essays of Montaigne than to anything popping up at the multiplex on a given Friday.

At this point, that strange irony – novels that steal from movies yet refuse to be stolen back – has tightened into a stranglehold. Anyway, I'm off with the multitudes to see if these TIFF films can break through the suffocation, and will leave the books at home alone to do what books do – await their fate in silence.