With the release of Paul Thomas Anderson's Inherent Vice in 2015, a director was finally able to complete the arduous task of adapting one of Thomas Pynchon's novels for the big screen. Save for the breezy Vineland (Pynchon's divisive 1999 novel) Inherent Vice remains perhaps the most easily accessible of the enigmatic author's work, though is nevertheless still head-meltingly difficult to follow even after a third, fourth or fifth revisit.

I make sure to note a disclaimer, before viewing Inherent Vice with friends, stating that you might not understand what goes on, but not to worry, because the characters feel this exact same way. Pynchon's work is notoriously dense, and for some to the point of frustration. His magnum opus, the expansive Gravity's Rainbow, (1973) for example, follows a cast of 400 characters across 760 pages, whilst the equally lauded Mason & Dixon (1997) frames its narrative through multiple unreliable narrators, and weaves through its prose the spelling, grammar and syntax of an 18th century document.

Postmodernist literature often confines itself strictly to that medium, with the style aiming to highlight the idea of expression through words, resulting in a sort of Mobius strip of reflexivity, drawing attention to the structure and style, and the act of reading itself. Pynchon's work largely eschews classical methods of description, development, sentence structure and narrative, to create an unfamiliar experience as opposed to a straightforward cause and effect page-turner.

Anderson's Inherent Vice took Pynchon's shaggy dog tale of a dope-smoking detective and Los Angeles land development (the closest to a conventional novel he has produced thus far) and moulded it into a near three-hour period-piece-cum-romance-cum-noir-cum-psychedelic-head-trip. However, despite efforts to stay true to Pynchon's vision, Anderson still found it necessary to do away with large swathes of the narrative, to amalgamate characters, and to tie off the intentional loose ends during the adaptation process, in order to craft Pynchon's complex vision into something remotely comprehensible and digestible for a wider audience.

Postmodernism in film is nothing new, with elements of the concept to be found as far back as The Great Train Robbery (1903) and as recently as Her (2013). Adapting postmodernist literature for film however, is a practice in its relative infancy. Never Let Me Go (2010) and American Psycho (2000) could both be considered postmodern literature adaptations, but their cinematic presence stretches the vital elements of the concept thin, and leans more towards straightforward narrative than the freewheeling non-linearity of the genre's most acclaimed work. A Scanner Darkly (2006), The Life of Pi (2012) and Fear and Loathing in Las Vegas (1998) came closer, with more daring and obtuse visual ideas on show, but the content becomes somewhat diluted under the strain of a constant emphasis on style.

With postmodernist literature often completely indebted to the written word, and designed and composed to specifically be consumed in that medium, the adaptation process can encounter a multitude of problems. Studios would rightly be wary of splashing a small fortune on a film version of Gravity's Rainbow, a book that tries its hardest to be near-incomprehensible, and to craft anything close to a three hour running time a director would have to cut out much of the excursive, nonrelated material that forms the structure, foundation and support of the main narrative thread. In untangling it, or deciding to cut seemingly insignificant passages, the film could potentially become infinitely less cohesive than the novel.

And so during my fourth viewing of Inherent Vice, I began to wonder which other postmodern novels could perhaps be adapted for film, and by which director, and what each novel would lose or gain through the process.

Infinite Jest - David Foster Wallace

Directed by: Paul Thomas Anderson

In what may go down as a defining moment of contemporary postmodern literature, the late David Foster Wallace explores the underlying, ever-present sadness and melancholy of an America that has been given everything it could possibly want. Concerning a prestigious tennis academy, the drug rehabilitation clinic adjacent, and Québecan separatists hunting the lone copy of a cartridge film so entertaining that the viewer will be compelled to watch until they die, it is a journey through the inner workings of the western world, and the idea of sadness at large.

DFW's book is a lengthy and complex rumination on modern living, transporting its narrative to a subtly dystopian continent where corporations bid for naming rights for each year (The action mainly taking place in 'The Year of the Depend Adult Undergarment) and a large area of southern Canada has been annexed as a sprawling hazardous waste dump.

One of the predominant stylistic elements of the book is the employment of cinematic crosscutting between strands of the plot. We jump from setting to setting, through time and space, and observe the events as they unfold, often simultaneously. This technique is one of the major reasons why Infinite Jest remains so captivating across its 1000 pages of story and 388 separate footnotes. Already the source material references both cinematic technique and film theory, with the protagonist's deceased father the director of the aforementioned deadly film cartridge, and could immediately suit the transition to the medium its plot orbits.

To do the novel complete justice, its director would likely have to fit in a number of categories. Focussing its attention so intently on America and American life, the figure at its head would likely benefit from being an American themselves. Secondly, their CV must boast work of length, as the sprawling narrative would need space in which to unfold. And thirdly, their style must be as intricately detailed as the complex prose here is.

An uninspired choice it may be, but I'm giving this one again to Anderson. Magnolia (1999) boasted a large interweaving cast, featured elements of the postmodern in its directorial style (the Aimee Mann sing-along, raining frogs) and, based in the heart of the San Fernando Valley, he has witnessed the best and worst that American culture and life has to offer. More inviting and with a more comfortable narrative flow than that of Inherent Vice, the adaptation of Infinite Jest could prove to be a somewhat easier task what with the novels endless debts to film culture and structure.

Would it work / 10: Yes, but it'd be very long.

The Crying of Lot 49 - Thomas Pynchon

Directed by: David Lynch

One of the pivotal moments in Pynchon's novella The Crying of Lot 49 reveals itself when protagonist, the out-of-her-depth housewife Oedipa Maas, gazes out over the city of San Narciso from a vantage point above.

"She looked down a slope, needing to squint for the sunlight, onto a vast sprawl of houses which had grown up all together, like a well-tended crop, from the dull brown earth; and she thought of the time she'd opened a transistor radio to replace a battery and seen her first printed circuit. The ordered swirl of houses and streets, from this high angle, sprang at her now with the same unexpected, astonishing clarity as the circuit card had. Though she knew even less about radios than about Southern Californians, there were to both outward patterns a hieroglyphic sense of concealed meaning, of an intent to communicate. There'd seemed no limit to what the printed circuit could have told her (if she had tried to find out); so in her first minute of San Narciso, a revelation also trembled just past the threshold of her understanding."

This borderline religious moment of understanding observes Oedipa as she draws comparisons between technology and humanity, the digital and the analogue, and the connections that draw us all together, whether these be artificial or charged through with intense energy. She instils a sense of meaning into the city below, and draws a personal interpretation from it, just as we do that passage of text.

A filmed version of The Crying of Lot 49 is definitely achievable; its page count being significantly shorter than any other novel listed here, but would require a director who has previously dealt with themes of metropolitan sprawl, conspiracy and the tragedy of circumstance beyond ones control.

Enter David Lynch then, seasoned veteran of the bizarre, unpredictable and symbolic. Both proudly and outwardly ambiguous, Pynchon and Lynch could prove to be a match made in heaven, or hell depending on your preferences towards relentless oddity. The dark tone Lynch utilised within Mulholland Drive (2000) could transfer effectively to the fictional San Narciso, and the postal system conspiracy that sees two historic mail delivery factions locked in a conflict is the stuff of a Lynch wet dream - unashamedly absurd yet played completely straight.

Would it work/10: "Despair came over her, as it will when nobody around has any sexual relevance to you."

Been Down so Long it Looks Like up to me - Richard Fariña

Directed by: Miranda July

Richard Fariña's first and only novel before his untimely death (which occurred just two days after the novel's release no less) sees him contemplate his own university experience through the guise of Gnossos Pappadopoulis: lovable rouge. A memoir as much as it is a hazy trawl through 1960's gender politics, the counterculture and the beat generations, and Cold War/Bay of Pigs era paranoia.

Written largely in slang, drawl and fashionable at the time idioms ("The conscience of my elusive race gives not a fig for me, baby. But I endure, if you know what I mean.") And so the script would likely be a delight to work with. Much of the dialogue could be lifted straight from the book without much tampering and still stylistically drive the film, and Gnossos' drug-fuelled visions and lust for adventure, the adaptation could possibly go some way to drawing in more of an audience than the cult novel ever did.

A magnetic protagonist, an ever-elusive end-goal, and a narrative that hops excitedly from revolutionary Cuba to opium dens to college campus and mansion parties, Been Down So Long It Looks Like Up To Me would need a cinematic style as energetic and immensely enjoyable as the read of its prose.

Miranda July, peddler of the candidly weird, purveyor of the wildly independent and voice for the unknowingly fashionable, cool and achingly hip, could prove to be a strong candidate. One criticism of the novel lies in its treatment of women (Caustic at worst, dismissive at best) and the presence of a female behind the camera could remedy this. July's idiosyncratic style would combine with the passionately individual style of writing, and with the recent release of her own debut novel (The First Bad Man) it is clear she has a solid grounding in, and understanding of, the nuances present in alternative literature.

Would it work/10: It's all gravy, baby.

Libra - Don Delilo

Directed by: Jonathan Glazer

Delilo's White Noise (1985) may be his most celebrated novel, considered to occupy the upper echelons of American postmodernism alongside Infinite Jest and William Gaddis' The Recognitions (1955), but it is his dissection, analysis and immersion into the Kennedy assassination, Libra (1988) remains his most outright filmable.

Partly included here because of the historical narrative in itself that the book draws from, and the files upon files of official documentation and speculation that surrounds the murder, but more so due to the stunning realisation of the novel's central character, Lee Harvey Oswald, Delilo's most thrilling creation/interpretation to date.

A murky plot concerns Oswald's childhood, emergence into the wider world and then his desire to find a place within it, alongside shady backroom government meetings, secret service shenanigans and a plot that draws together numerous real and fictional figures of note, who all play their cards to their respective chests until the final moment.

Oliver Stone tackled the narrative in typical bombastic fashion back in 1991 with JFK, but Delilo's plot here is much more taut and tightly wound, and rejects the conspiratorial tone of Stone's work, playing off his own analyses as fact through punchy, fractured prose. Jonathan Glazer, director of Sexy Beast (2000) and Under the Skin (2013) would suit the darkness of Delilo's creation, and though only three features deep into his career, has displayed a consistency, thoughtfulness and attraction to the evils of men that rival's Delilo's own.

Glazer's penchant for fractured, ambiguous jumps in logic and space could also go some way to capturing the disorienting texture of Libra as we hop from Dallas to the USSR to the backrooms of Washington and beyond. Libra is speculative in its essence, and just as Glazer's audience during Under the Skin were asked to draw their own answers from the obtuse material they were given, so too here are Delilo's readers, left in the dark and the cold with very little explicit closure to be found.

Would it work/10: See: Glazer's Guinness advert, the best there'll ever be.

One Hundred Years of Solitude - Gabriel Garcia Marquez

Directed by: Claire Denis

Magical realism is the creative insertion of magic into a rational world, and, though not strictly confined to literature, has become largely synonymous with that medium. In this style, Gabriel Garcia Marquez's One Hundred Years of Solitude traces the fortunes of seven generations of the Buendía family, in the town of Macondo, which their ancestors founded.

As the book progresses, the misfortunes that befall the family, and the figures that visit the town, become increasingly surreal, otherworldly and mysterious. Layered with enigma, existentialism, philosophy, ghostly apparitions and the damaging presence of time itself, Marquez's masterpiece sees Macondo, the town of mirrors, as a symbol for inevitability, cyclical repetition and alienation from the wider world.

Mirrors become mirages and eventually we, as readers, are lost in the same labyrinth of time and space as the entire Buendía family tree always was, and always will be. Who better to undertake the task then, than Claire Denis, a seasoned master of hazy, quietly surreal and highly detailed spacious imagery? With Beau Travail (1999) Denis highlighted her firm grasp of the space between our world and something less familiar, straining to remain in a limbo between reality and a place where, though seemingly normal, presents itself as just not quite right.

Denis' One Hundred Years of Solitude would perhaps follow down this path of reality intertwined with distant, indefinable 'magic', and also demand her style adapt to cater for an intricate study of a large group, as opposed to the singular, individual character focus she has long displayed.

Would it work/10: A shout out to you, if you've read this far.

The Mezzanine - Nicholson Baker

Directed by: Chris Marker

The entirety of Nicholson Baker's debut novel The Mezzanine takes place during a lunch break. In the time it takes for its main character to reach the top of an escalator, the novel captures in a winding stream of consciousness the everyday thoughts of a man if they were given time to reach their logical conclusions. Intersecting the literary style of David Foster Wallace The Mezzanine includes vast footnotes and endnotes, which often take up much of the page, inserting thoughts into thoughts and so on.

Of all the hypothetical adaptations here, this would perhaps be the most challenging. I'm a firm believer that there is no such thing as an un-filmable novel, but The Mezzanine is about as close as it's going to get. There are films that unfold within a small amount of space (See: Buried, Locke, Rope), and films that take place in real time (Timecode, Failsafe, My Dinner with Andre) but to set both elements within the space of a short elevator ride, along with lengthy explorations of incredibly mundane ideas, would be truly difficult.

However, if there were anyone up to the task, it would be Chris Marker, from beyond the grave. Marker's landmark Sans Soleil (1983) unfolds as a voice narrating a letter over a procession of brief images, creating a collage of ideas that mirrors the passage of memory as it passes through interpretation. A female voice reads out a stream of poetic correspondence to the viewer, and in it is captured towering concepts, and Marker's entire perspective on life itself - A truly remarkable film, by a truly remarkable filmmaker.

Perhaps the young office worker, named Howie in Barker's novel, could read aloud the original writing, to be accompanied by the imagery relating to it, so as to slow the passage of time, or substitute the concept of time and place altogether, as Marker does so effectively in Sans Soleil. Where the other novels here, whether they seem to initially or not, all contain a plot of some kind, a series of events and moments that effect the next and so on, The Mezzanine features none of the sort, none of that shit, and rejects plot and narrative entirely to make space for expansive and unabridged thinking.

If it were to be filmed, Barker's vision runs the risk of ending up a complete shambles. With a suitable level of creativity involved we could end up with something resembling the book, but to truly capture the style and effect and the driving force behind The Mezzanine the adapter would perhaps need to never pick up the book at all, and instead go on their own elevator ride / existential meander / philosophical lunch break, to produce something as singular as this.

Would it work/10: Not happening.