Classics never die, but they seldom get replaced. Cinema is populated with enduring, venerated works of art that deservedly adorn list after list, but those lists are rarely updated, and less often expanded to include new, equally worthy entries. Organizations that give out annual awards are constrained not only by the limitations of formatting, but perspective - they can’t anticipate which film will survive the buzz of its initial acclaim or success and become part of the cultural firmament. And then there are just certain films or even genres that too infrequently receive the critical attention they deserve, are too obscure to break through to bigger audiences, or just aren’t taken seriously enough to merit consideration alongside the ones we “all” already know we love or respect. A Case For Greatness, this series, tries to argue for, and to champion, forgotten or underappreciated films in a variety of genres that may be worthy of being called “classics.”

Is it better or worse to have done great work and be unable to follow it up than to never have done anything at all? In an industry like journalism or film criticism it often feels like another “big” story is right around the corner - there always seems to be another important movie or piece of news to be written about or analyzed. But speaking from personal experience, the challenges of consistent employment, the priorities of different editors and the shifting winds of the zeitgeist make it tough to align talent, access and perhaps most importantly, the right timing to properly seize upon those opportunities. All of which is to say that even though I’m not exactly the same kind of writer as Grady Tripp, I find myself relating strongly to the quandaries of him and several other characters in Curtis Hanson’s Wonder Boys, a delightfully shaggy film about talent nurtured, promises made and expectations fulfilled.

Curtis Hanson’s follow-up to the Oscar-winning L.A. Confidential was, upon its release in February 2000, a commercial failure - and it failed again when Paramount decided to try and find an audience in November of the same year with a rejiggered marketing campaign. But many of those who saw it (during either run) immediately recognized its humor, honesty and heart, the story of Grady (Michael Douglas), a critically acclaimed novelist-turned-professor whose follow up book is 2600 pages and counting, and its ending only keeps getting further away. His marriage to his third wife Emily has just ended and he’s having an affair with Sara Gaskell (Frances McDormand), the wife of the chairman of the English department at his college. Just as his editor, Terry Crabtree (Robert Downey Jr.), arrives in town to check on the book’s progress, Grady unwittingly becomes the caretaker of James Leer (Tobey Maguire), a promising young student that he worries may be suicidal.

Based on the book of the same name by Michael Chabon and adapted by Steve Kloves, who emerged from a self-imposed seven-year retirement to write the script, Wonder Boys is a deliciously, indulgently literate film, not just relishing in the discovery of language that these writers of various skill levels make in their work, but in acknowledging and deconstructing the cliched positions they’re put into via their various role within this community, and their own lives. Grady, milling around his house in a shopworn pink robe, scrounging for a rediscovered joint left forgotten in the pocket, has become the embodiment of a middle-aged novelist, and he is all too aware - moreso, even, because of the tremendous success of his first book. But that persona has also become its own comforting shroud, a protective cover from actually completing his book or reconnecting with the inspiration - or even just motivation - that drove him earlier in his career, and his life.

Kloves manages to make the characters’ self-awareness feel lived in and honest rather than expository, shuffling the responsibility for these characters understanding themselves to one another as they deal with issues of both immediate and long-term significance. While showing James a coat worn by Marilyn Monroe hidden away in a safe in Sara’s house, Grady gets viciously attacked by their dog Poe and James shoots and kills the dog with a small pistol. The duo’s dealing with the corpse becomes no small source of humor, but it also provides Grady with a constant reminder of not one but two uncomfortable confessions he needs to make to Sara - first about their pet, and then his true feelings for her. Maguire’s James, meanwhile, is a fount of dishonesty, an uncommonly keen observer of human nature who has concocted elaborate fictions to disguise his own privileged and fairly boring upbringing, but it all serves not just his art but an adult life he desperately needs Grady’s guidance to begin to safely explore.

Downey, who was on probation at the time, convinced Hanson to cast him as Crabtree, the alternately idealistic and predatory editor who targets James as his next conquest but does so as much as anything out of his own desperation - he hitched his wagon to Grady’s talent, and has willingly, if unhappily, lost his own stature as a result. The three men all deliver these great, unique, lived-in performances that feel authentic, funny and believable, whether they’re conspiring to cover up a dog’s murder or speculating for fun about the name and vocation of “Vernon Hardapple” (Richard Knox), a barfly with James Brown’s haircut. Meanwhile, McDormand seems to be advancing towards her final Three Billboards form as Sara, Grady’s secret lovestruck but pragmatic secret girlfriend. She’s just the kind of woman that Grady needs, which is probably what makes her so frightening for him to be honest with, and their relationship reinforces a central theme, eventually articulated by Downey’s Crabtree about how we often put ourselves in situations without realizing that force us to make choices, or maybe make choices for us.

It’s a hard thing to understand or accept - that everything we are doing is putting us into a position of success or failure - but sometimes the feeling of doing nothing is precisely the kick in the pants that we need to get us going again. Hanson’s film astutely observes that people around us frequently see us better and clearer than we see ourselves, and it’s important to rely upon them for honesty and insight if we’re going to make the changes to achieve the goals that we think we’re working tirelessly towards. Additionally a movie about how fiction often gives way to greater truths, Wonder Boys ultimately has a wonderful novelistic quality that understands structure and convention to get at something interesting and special, reminding us that on our individual paths, knowledge and experience often obfuscate curiosity and discovery, distractions frequently shed light on what’s most important, and most of all, meandering and just the act of getting lost can often lead us to right where we are meant to be.