Jan 8, 2015 · 7 minutes

Read any review of Paul Thomas Anderson's newest film, Inherent Vice, and you'll almost certainly find the word "unfilmmable." That's the phrase many use to describe Thomas Pynchon, that towering figure of post-modern verbosity behind the novel on which the film is based. His books overflow with ideas, characters, subplots, and jokes -- many of them brilliant, some of them forgettable, and, taken in full, they are both maddening and thrilling for readers.

But if there's any director up to challenge of filming the unfilmmable, it's Anderson. The script to The Master often reads like a two-man play; yet from these intense, unnerving stretches of dialogue, Anderson spins an epic narrative about religion, sex, and post-war America. That film's uncomfortably long shots, with frames dominated by faces lost in an abyss of darkness, telegraph the kind of internal human strife generally reserved for great novels. There Will Be Blood accomplishes a similarly daunting task but does it through silence, the things left unsaid filling the void of that film's expansive West Texas landscapes. And in Punch Drunk Love, Anderson captures the contours of a mind on the verge of insanity, weaving together a visceral and chaotic tapestry of motion and sound.

No director alive lodges viewers inside the minds of his characters -- again, an exploit generally reserved for novels -- like Anderson.

His latest, Inherent Vice, is no exception. Joaquin Phoenix plays Doc Sportello, a perpetually-stoned private detective living in Southern California who stumbles upon a comically complex conspiracy involving Jewish land developers, neo-Nazi bodyguards, hippies moonlighting for the FBI, dentists moonlighting as drug dealers, and a global heroin syndicate. One part The Long Goodbye film noir and one part Naked Gun slapstick, Inherent Vice tells a hilarious and sad mystery that blurs the line between dope fiends, housewives, cops, and millionaires until all that's left are the powerful and the powerless. The plot is too complicated to understand, but that's the point: It's a reflection of the web of institutional corruption and sin that causes a litany of tragedies inflicted on the disempowered everyday. It's a Whodunnit, only insofar as the "Who" is the greed of the power-hungry and the "It" is the naiveté of counter-culture types who dared to be good.

So if Anderson can pull off Inherent Vice, all while remaining extremely faithful to the source material, somebody should tackle Pynchon's most recent novel, Bleeding Edge, which is set in "Silicon Alley" between the popping of the first Internet bubble and the September 11 attacks. Like Inherent ViceBleeding Edge follows a detective who tries to uncover an impossibly complex conspiracy, only this time it involves tech entrepreneurs, shady venture capitalists, the Russian mob, Islamic radicals, and Mossad. (There's a recurring theme here in Pynchon's conspiracy tales -- People with wildly divergent ideals and values -- like Jews and Nazis, or the FBI and al Qaeda -- will come together in the pursuit of money and power).

How would such a movie take shape? Who would direct it? Who would star in it? Let's take a not-at-all-scientific and wholly-fantastical stab at answering these questions:

Director: It's tempting to suggest that Anderson once again take the reins, having already proven himself as the only director talented and intrepid enough to adapt Pynchon. But he's a Los Angeles guy front-to-back, and Bleeding Edge might be better left in the hands of a director whose familiarity with New York allows the filmmaker to turn the city into a character itself, like Anderson has done with LA. Martin Scorsese obviously comes to mind; he's already captured the corruption and excess of moneyed East Coast elites in Wolf of Wall Street.

But despite the fact that Scorsese may be America's greatest living director, his more recent films are so slick and stylish that they fall short in capturing the grime and filth of New York's underbelly like his older movies did. And much of Bleeding Edge focuses on the darkest, seediest corners of NYC that were left untouched by Mayor Giuliani's cleanup efforts and the massive allocation of wealth brought in by the tech industry.

Instead, let's give the job to rising star J.C. Chandor. Over the past four years, he's deftly captured both the corporate side of New York, with the superb tick-tock retelling of the initial stages of America's financial collapse in Margin Call, along with the gritty, violent side of early-80s New York in 2014's A Most Violent Year.

Maxine Tarnow

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In the book, one character describes the protagonist Maxine, a fraud investigator raising two children as a single mom, as a dead ringer for Rachel Weisz. But while Weisz is a good actress, the words "hardened" and "cynical" and "street-smart" -- traits that undoubtedly define Maxine -- don't often come to mind when thinking about her roles. Maybe she could pull it off and carry a movie all by herself, though most of her best performances have been supporting roles. The part of Maxine, however, which requires the actor to be at turns brilliant, sexy, hilarious, and terrified, requires not just a great actress, but one of the best actresses of her generation. I know she's not Jewish like Maxine, nor does she even remotely look the part, but who cares: Kate Winslet is maybe the only actress alive with the grit, intelligence, comedic chops, and emotional range to do this role justice.

[photo by maggiejumps]

Gabriel Ice

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Ice is a boy billionaire CEO and pure evil, so it's tempting to suggest Jesse Eisenberg for the role. (His portrayal of Mark Zuckerberg is much more similar to Ice's character than Zuckerberg himself). But that seems too easy. Eisenberg plays the part of the boyish dick better than anybody, but despite his capacity for evil, he's not scary like Ice. Dane DeHaan, howeverthe hero-turned-murderous-villain of Chronicle and the disturbed, fatherless young man in Place Beyond the Pines, is downright terrifying despite his youthful exterior.

[photo by Christopher William Adach]

Reg Despard

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I'd love to see Jamie Foxx in the role of Maxine's de facto sidekick. Not the determined, confident Jamie Foxx of Django Unchained but the nervous, paranoid, perpetually-in-over-his-head Jamie Foxx of Collateral.

[photo by Georges Biard]

March Kelleher

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Ice's mother-in-law, once and future activist, and filthy rich. This requires an actress in her 60s with a ton of fire left in her belly. Have I mentioned how much I'm dying to see Goldie Hawn make a comeback?

[photo by Siebbi]

Nicholas Windust

Ed_Harris

A CIA operative involved in basically every terrible thing that the United States has ever done. And yet despite (or because of?) the fact that he represents everything Maxine hates, she is uncontrollably attracted to him. Evil? Older? Arrogant? Ed Harris, all day.

[photo by Lcsulla]

Heidi Czornak

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Maxine's best friend, who in many ways still lives the party lifestyle she left behind. Rosario Dawson's mix of sexiness and smarts -- both street and book -- make her perfect for the role.

[photo by Dyspepsion]

Horst Loeffler

Kevinnealon

Maxine's ex-husband -- a nice guy and good with numbers, but a total buffoon about everything else. Kevin Nealon is a comic genius who I'd love to see get more work than those sad "pump-you-up" State Farm commercials.

[photo by sarahinvegas]

Eric Outfield

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Weirdo hacker with an addiction to foot sex. Weirdo human Jimmi Simpson (aka Liam McPoyle from Always Sunny) should reprise his hacker role from House of Cards, where he plays basically the same character.

[photo by Bedside]

Ernie Tarnow

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Maxine's parents don't play a huge part in the book, but her father Ernie delivers one of its most unforgettable monologues toward the end of the novel, summing up much of what Pynchon had gone on about for the previous 500 pages. There's nothing like seeing a legendary actor come on screen for one spectacular monologue before dropping the mic. And since this is all fantasy anyway, let's call Gene Hackman out of retirement. Maybe it's not such a ridiculous idea: After all, he did tell GQ he might consider a return to acting "if I could do it in my own house, maybe, without them disturbing anything and just one or two people."

[photo by Trish Overton]

Rocky Slagiatt

Fred Wilson

Slagiatt is a big shot New York VC, so let's take a chance in service of verisimilitude and cast Fred Wilson. He's no actor, but he put on quite an entertaining performance at one of our PandoMonthly chats.

[top image via VeryPhil]