Photo by Focus/Kobal/REX/Shutterstock
50. Sylvia (2003), directed by Christine Jeffs
Sylvia Plath deserves a better biopic. As they didn’t get the rights to her poetry, Paltrow’s version of the doomed poetess is the most annoying girl in your class, the one who’s always reciting whole swaths of arcane poetry just to prove how smart she is. Daniel Craig, also, is far too short to believably have any of Ted Hughes’ physicality. The mood is right, and the scenery is beautiful, and the occasional Boston Brahmin accents are annoying, and if you are a girl who had a Plath phase, you may find this film to have a goofy camp appeal.
49. Finding Forrester (2000), directed by Gus Van Sant
Van Sant’s big budget follow-up to Good Will Hunting, this plays a bit like Good Will Hunting 2: Hunting Season (same young man/old man mentorship ideas) with all of the idiosyncrasy leeched out. Young Jamal Wallace (Rob Brown) is a good basketball player and secretly a writing prodigy, and when he falls into the life of gone-to-seed writer and recluse William Forrester, a beautiful friendship is formed. This film is pure cheese, one of the infrequent films to feature a black protagonist* as a writer, and its most memorable moment is a writing scene — a writing scene! — that’s become a meme, with Sean Connery cheering the young writer on as he types on a typewriter in his inimitable burr, “Punch the keys for God’s sake! Yes, yeeeessss! You’re the man now, dog!”
*Due to the parameters, this list skews a lot on the side of Woody Allen films and biopics of various British writers and nearly every American writing era, save, oh, the Harlem Renaissance. Someone really could make the definitive film about Zora Neale Hurston. I’d watch it! There’s also a distinct lack of adaptations of great Black literature, too, which is a topic that critic Wesley Morris discusses in this great piece for The Boston Globe, and not much has changed since 2010.
48. Total Eclipse (1995), directed by Agnieszka Holland
Is there anything cuter when an attractive young actor follows up a breakout monster hit with a small indie movie? (Do you remember Robert Pattinson playing Salvador Dalí?) Well, unfortunately the windmills of my mind were inaccurate regarding this film — it was Leonardo DiCaprio, by then an Oscar-nominated, always edgy young actor, making another idiosyncratic choice before he ended up in Titantic. DiCaprio makes a good sadistic young teen poet Arthur Rimbaud, who falls in love with Tom Verlaine. Forbidden romance and tragedy ensues.
47. Mrs. Parker and the Vicious Circle (1994), directed by Alan Rudolph
Jennifer Jason Leigh is downright uncanny as Dorothy Parker, the doyenne of the Algonquin Round Table. The rest of the film is beautiful and lushly put together… it just suffers from a fidelity to the characters at the expense of being a movie. Just like a movie about writers.
46. Deathtrap (1982), directed by Sidney Lumet
With his adaptation of Ira Levin’s play, Sidney Lumet brings an elegant touch to a story that starts with one older playwright, hungry for a hit, inviting his younger student to his fancy Long Island house for a visit to the country. The ensuing fun is diabolical.
Photo by Richard Sylvarnes/True Fiction/Kobal/REX/Shutterstock
45. Henry Fool (1997), directed by Hal Hartley
Henry Fool is a wit and an unpublished novelist, and when he meets Simon Grim, he’s ready to show his garbageman friend about the world of literature. Inspired by Henry, Simon starts to work on the “great American poem,” and from that poem comes a whole river of absurdist comedy. Also: Parker Posey! And the second Henry Fool sequel, Ned Rifle, played the Toronto Film Festival earlier this year, with Aubrey Plaza adding her deadpan to this world.
44. Manhattan (1979), directed by Woody Allen
“It is … a breathtaking hymn to the idea of being in love in Manhattan, a place Allen loves. The opening shot is a stunner, looking West across Central Park at dawn while Gershwin’s ‘Rhapsody in Blue’ does what it always does — makes us feel transcendent. The locations are like an anthology of Manhattan shrines: The characters visit the Guggenheim, Elaine’s, Zabar’s deli. They sit on a park bench at dawn beneath a towering bridge, and ride a carriage through Central Park, and row boats in the lagoon. They go to art movies and concerts and eat Chinese food in bed and play racquetball.” — Roger Ebert
43. Barfly (1987), directed by Barbet Schroeder
Charles Bukowski wrote the screenplay for this kinda autobiographical story about a dude who lives in bars and yet is also a very good writer. It features Mickey Rourke when he was at his Brando-iest and prettiest, and it’s all about authenticity regarding a life in bars versus a life in letters.
42. The Pillow Book (1996), directed by Peter Greenaway
The Pillow Book by Sei Shonagon is one of the first “books” ever. It is a leading ur-text of humanity, and it’s a remarkably modern-feeling read. This crazy Greenaway film is about a model obsessed with calligraphy and poetry (particularly all over Ewan McGregor’s entire body), ulitizing Shonagon’s insights and life to create a bananas art film.
41. My Left Foot (1989), directed by Jim Sheridan
“Most famously, in [Daniel Day-Lewis’] first Oscar-winning role, as the Irish artist Christy Brown who had cerebral palsy in Jim Sheridan’s My Left Foot, he spent almost the entire shoot in a wheelchair. ‘He’d call you by your film name, and you’d call him Christy. It was madness. You’d be feeding him, wheeling him around. During the entire film, I only saw him walking once,’ Sheridan’s daughter, Kirsten Sheridan, later recalled.” — Geoffrey MacNab, The Independent
Photo by John Clifford/Good Machine/Hbo/Kobal/REX/Shutterstock
40. American Splendor (2003), directed by Shari Springer Berman and Robert Pulcini
Harvey Pekar’s American Splendor comics are a marvel that expanded what comics could do with their humdrum tales of Pekar’s American life. The resulting film adaptation was sweet, evanescent, and meta, with one of the first big leading roles for Paul Giammati as Pekar, who’d break the fourth wall and talk straight to the camera.
39. Swimming Pool (2003), directed by François Ozon
Charlotte Rampling goes off to a secluded French house in order to write her mystery novel, when a lovely French drifter shows up and wreaks some psychosexual havoc, as French drifters do. That’s the tag line, but you can never really trust a mystery novelist, can you?
38. The Front (1976), directed by Martin Ritt
Woody Allen takes on one of his few sole acting roles in this film about the Hollywood blacklist. Technically, Allen’s character, Howard Prince, isn’t quite a writer — he just signs his names to scripts from blacklisted artists — but with that action, he ends up as “the front” for a variety of writers. The Hollywood Blacklist era isn’t talked about as much as it should be, and this is one of the slim list of films that wrestles with something that, as much as we forget, happened, and it happened recently.
37. The Royal Tenenbaums (2001), directed by Wes Anderson
“Well, everyone knows Custer died at Little Bighorn. What this book presupposes is… maybe he didn’t.” This film about a depressed family of former child geniuses features one playwright, Margo Tenenbaum (Gwyneth Paltrow at her best), and a pitch-perfect parody of absurdist masculinity in Owen Wilson’s character. He’s a faux Cormac McCarthyish writer, photographed for fancy magazines in black-and-white, holding snakes aloft, wearing a cowboy hat, presupposing and friscalating all over the place. “The crickets and the rust-beetles scuttled among the nettles of the sage thicket. ‘Vámonos, amigos,” he whispered, and threw the busted leather flintcraw over the loose weave of the saddlecock. And they rode on in the friscalating dusklight.”
36. Ruby Sparks (2012), directed by Jonathan Dayton and Valerie Faris
Perhaps known to you as the “anti-manic pixie dream girl movie,” which is a pretty shallow reading of it, Ruby Sparks is a dark commentary on relationships. With Paul Dano as a dweeby writer who realizes that he can literally write his perfect girlfriend into existence, Ruby Sparks shows the thrill of initial connection before wading into disturbing waters regarding the writer’s responsibility over their creation that they are also ostensibly in a loving relationship with. Whether or not they stuck the landing, it’s a provocative and smartly scripted work from Zoe Kazan, who also stars.
Photo by Snap/REX/Shutterstock
35. Impromptu (1991), directed by James Lapine
Judy Davis makes for a good writer, and in the delightful Impromptu, she’s wearing pants (!) in the 1800s (!!) because she’s playing the real-life writer Baroness Amantine-Lucile-Aurore Dupin, aka George Sand, a divorcee who has loads of glamorous affairs with men like Frederic Chopin (Hugh Grant) and lives a life beyond the rules for a lady of the time. She wore pants, she wrote under a male pseudonym, and she was a total wit. The film in her tribute is loads of fun.
34. Kill Your Darlings (2013), directed by John Krokidas
The Beat Generation! Basis of all books! Source of many films kind of insufferable and kind of flabby! But you know what? Krokidas creates some sort of magic here, with flipping Harry Potter himself (Daniel Radcliffe, who is a good actor) playing Allen Ginsberg. Perhaps it works because it’s a portrait of the artists as they met at Columbia, with Ginsberg and Burroughs and Kerouac all sparking off each other. But the real spine of the plot comes from a murder, not the fact that these guys would become great artists. Plus: Dane DeHaan!
33. Contempt (1963), directed by Jean-Luc Godard
“A tragic love story in a wonderful setting!” the trailer chirps, and Contempt is one (of the many) French New Wave films to wrestle with the writing process and how to make art out of it. A novelist, estranged from his babe wife (Brigitte Bardot), is hired to make a proper script out of Homer’s The Odyssey for a massive film spectacular. Art versus commerce is the topic of the day, with the inherent drama of disintegrating marriages on top of it.
32. Prick Up Your Ears (1987), directed by Stephen Frears
This film put Gary Oldman and Alfred Molina on the map — playing playwright and writer Joe Orton and his boyfriend Kenneth Halliwell. Orton is younger, but life is more generous to him. His writing career takes off while Haliwell stews. It’s the story of a relationship that isn’t equal, and Orton’s writing is the catalyst for a series of unfortunate events.
31. Adult World (2013), directed by Scott Coffey
This film nails what it’s like to be a recently graduated shithead with visions of being the world’s next Great American Poet (you are kind of annoying and naive), and it’s also very funny in its portrayal of what it’s like to be the formerly Young and Hot Edgy American Poet, but now you are old (which is the perfect John Cusack role). It is wry, funny, and very sweet regarding what it’s like to want to create great art, but to have too little writing experience, or to be too burnt out, to get anything great on the page.
Photo by 20th Century Fox/Kobal/REX/Shutterstock
30. Julia (1977), directed by Fred Zinnemann
Based on a book by Lillian Hellman, supposedly based on a true story, Julia has Jane Fonda as the faux Hellman, a struggling writer entangled with her friend (who fought the Nazis.) The writer/director relationship was fractious — regarding Hellman’s penchant for fabrications, Zinneman said: “[She’s] an extremely talented, brilliant writer, but she was a phony character, I’m sorry to say. My relations with her were very guarded and ended in pure hatred.”
29. Poetic Justice (1993), directed by John Singleton
The follow-up to Singleton’s Boyz in Da Hood, this film had Janet Jackson as a shy and talented poetess (her poems were written by Maya Angelou) who, after the shooting death of her boyfriend, goes on a roadtrip to Oakland with her friends and eventual love interest Tupac Shakur. Receiving mixed reviews on its release, the film does have its cult following, and Kendrick Lamar’s single “Poetic Justice” from Good Kid, m.A.A.d. City sampled Jackson’s Oscar-nominated song from the film, “Again.”
28. Fellini’s Casanova (1976), directed by Federico Fellini
Besides being quite the lover, Casanova was also a writer, and who better to bring his surreal visions to life than Federico Fellini? This film is trippy as hell, based on a Casanova biography, and a freak show journey into sexual deviancy. Also, that’s an unrecognizable Donald Sutherland in the lead role.
27. Shakespeare In Love (1998), directed by John Madden
Tom Stoppard wrote this captivating film about how Shakespeare’s muse — Gwyneth Paltrow, wanting to act so hard she dressed up like a man — inspired him to write some of the greatest words of all time. It’s funny, witty, and you really root for Paltrow and Shakespeare to make it, after all, even if Ben Affleck’s walking around in tights somewhere.
26. The Motorcycle Diaries (2004), directed by Walter Salles
Before Che Guevara was “Che,” he was a young medical student traveling South America on his motorcycle with his best friend. The resulting journey was where his political consciousness blossomed, as he wrote about in his travel diaries, and Walter Salles’ film does a superb job of bringing this change to visual life. No wonder he eventually directed the long-in-the-works On the Road movie (but it’s still not that good).
Photo by Gravier Productions/Kobal/REX/Shutterstock
25. Midnight in Paris (2011), directed by Woody Allen
Now that everyone’s gotten over the fact that this slight Allen picture has an unfuckwithable, porn-for-English-majors-and-aspiring-writers-alike premise, can we also admit that it features female characters who are mostly shrews, dopey muses, Gertrude Stein (a font of wisdom), and/or twenty years old and French (perfect!)? Or should we just enjoy Owen Wilson’s laconic surfer charm, which makes him a darn good substitute for the Allen character, neurosis-ing his way around the Left Bank and running into all his hero writers from the Lost Generation, hanging with the hilarious Hemingway and all sorts of chums, creating a Parisian magic that’s full of nostalgia and whimsy. Fine, so it’s half of a kind of wonderful movie, but it stranded Rachel McAdams and that should be unforgivable.
24. Iris (2001), directed by Richard Eyre
There is one problem with this classy Iris Murdoch biopic about vibrant young genius Iris Murdoch (Kate Winslet) and her slip into dementia in old age (beautifully embodied by Judi Dench) — as an introduction to Murdoch, it fails to illustrate that she was a rip-roaringly hilarious writer, too. But it is a lovely portrait of an artist, and a marriage, as it begins and as time takes its toll.
23. Before Sunset (2004), directed by Richard Linklater
Of course Ethan Hawke is playing a fucking writer. Of course. That’s like James Franco playing a writer in a movie. But in part two of Richard Linklater’s sublime film series (currently a trilogy, but we know/hope it will go on forever), Hawke’s Jesse comes back to Paris for a book reading at the sainted Shakespeare and Company. In fact, he had written a book about his magical encounter with Celine. When they meet again, some magic strikes, leading to one of the best final scenes in cinema. “Baby, you’re going to miss that plane.”
22. The Door in the Floor (2004), directed by Tod Williams
Based on the John Irving novel A Widow For One Year, The Door in the Floor takes a sliver of that sprawling story and puts it on screen. Jeff Bridges is a drunken children’s book writer, having affairs; when he hires an admiring local teenager and aspiring writer to work for him, the teen learns some lessons about life and writing. (Namely, maybe it’s better not to drink.)
21. Fear and Loathing in Las Vegas (1998), directed by Terry Gilliam
Hunter S. Thompson’s druggy visions of America are catnip to the right sort of actor/director combination, but nobody does it better than Thompson’s real life pal Johnny Depp. Gilliam’s a perfect match for this material, making Thompson’s narrative into visual chaos, a perfect metaphor for 1960s America.
Photo by Snap/REX/Shutterstock
20. Misery (1990), directed by Rob Reiner
Can we come to the conclusion that Stephen King has a lot of angst around writing? Or that writing, for him, is a… horror? In this thriller, James Caan is a writer rescued and kidnapped by his biggest fan, played by Kathy Bates, who won an Oscar for the role. She loves his work so much that she tortures and threatens him into writing a special book just for her. Bloody good havoc ensues, put together expertly by best screenwriter ever William Goldman and the sometimes-underrated eye of Rob Reiner.
19. Before Night Falls (2000), directed by Julian Schnabel
The second film by artist Julian Schnabel, this visually stunning biopic got an Academy Award nomination for Javier Bardem, who’s a revelation as the Cuban writer Reinaldo Arenas. The writer was thrown in prison repeatedly for trumped-up charges in the ’70s (where we see Johnny Depp in his small cameo), because he was openly gay in a difficult political climate. It’s an infuriating, strange, and beautiful work, with some scenes that will linger.
18. Deconstructing Harry (1997), directed by Woody Allen
Another film about a writer featuring Judy Davis! But also that guy Woody Allen. This is a deep trip into the writer’s mind, with Allen on some Igmar Bergman shit, showing us scenes from Harry Block’s life, the important choices he’s made, the hell that he’s in, as he goes on a drive to get an award. Is it secretly a film about Philip Roth, where Roth goes to hell? Maybe, maybe not, but isn’t it funnier to think so?
17. The World According to Garp (1982), directed by George Roy Hill
Another John Irving book adaptation? Yes, of course. This one has Garp (Robin Williams), a struggling novelist, whose whole life changes once his formidable mother publishes a book. That book’s called Sexual Suspect, and it turns her into a feminist icon, with followers and everything. Garp, on the other hand, publishes a novel. But really, this film uses writing as a jumping-off point to explore gender roles and gender, as it was perceived in the early ’80s.
16. The Hours (2002), directed by Stephen Daldry
“The Hours? More like the weeks!” said Liz Lemon in a 30 Rock episode, and she’s half-right in this case. Nicole Kidman puts on the fake nose in order to play Virginia Woolf, prepared to walk into the River Ouse with stones in her pockets, and the scenes are intercut with visions of women who can be considered Woolf’s daughters: Julianne Moore as an uptight, possibly lesbian housewife; Meryl Streep as a modern-day Mrs. Dalloway throwing a party.
Photo by Moviestore/REX/Shutterstock
15. Naked Lunch (1991), directed by David Cronenberg
“Joan Lee (the stalwart Judy Davis, one of only two women in the cast) is introduced injecting her chest with bug poison. ‘It’s a very literary high, it’s a Kafka high — you feel like a bug,’ she tells Bill [Burroughs]. To watch Davis idly kill roaches simply by breathing on them is to see the real Morticia Addams. Davis and [Peter] Weller are a pair of hollow-eyed cadavers — all the more so when, like the actual Burroughs, Bill Lee decides that it’s ‘time for our William Tell routine’ and, aiming for the glass on Joan’s head, undershoots it by several critical inches.” — From J. Hoberman’s Village Voice review
14. Starting Out in the Evening (2007), directed by Andrew Wagner
Frank Langella is a fine actor to play a writer, as he has an inner light that’s basically impossible to snuff out. In this adapation of Brian Morton’s great novel, he’s a 70-something nearly forgotten novelist, Leonard Schilling, and Lauren Ambrose is the ambitious grad student determined to bring Schilling back into the public conversation with his thesis. Something like May-December ensues, but it’s love as a thrillingly intellectual conversation that never ends.
13. Bright Star (2009), directed by Jane Campion
Jane Campion brings her inimitable eye to the story of John Keats and his love Fanny Brawne. They fall for each other, body and soul. There’s a section of the film where they send love letters to each other, and it may be one of the swooniest literary seductions on film. There’s magic in seeing the word-drunk romance of these two characters.
12. Young Adult (2011), directed by Jason Reitman
While this film got press for being about an unlikable character — which it is! Unapologetically! It’s great! — it’s also even better about the writing process; Charlize Theron’s Mavis is a successful ghostwriter for a teen series, and we see her process at work. Teen girls chatter in a Target, and she’s listening, and you can see her turning their minutia into dialogue and plot.
11. Certified Copy (2010), directed by Abbas Kiarostami
Perhaps Certified Copy is the ur-example of a movie that is about a writer stating what the thing is about, and the film echoing the shape of his words. In this case, it starts with a British writer giving a talk called “certified copy,” which says that authenticity is irrelevant in art since everything’s a copy… and regarding this writer’s mysterious relationship with Juliette Binoche, which waxes and wanes and playfully rearranges your mind over the course of the film, maybe that’s a copy too?
Photo by Columbia/Kobal/REX/Shutterstock
10. A Man For All Seasons (1966), directed by Fred Zinnemann
Sir Thomas More, author of Utopia, was a deeply principled man. A humanist. A saint. In this Best Picture-winning theatrical adaptation, we watch how More’s principles — he refused to let Henry VIII annul yet another marriage — shaped the outcome of his life. He was a man who revealed great morality and ethics in the process, and this stately film pays fine tribute.
9. The Shining (1980), directed by Stanley Kubrick
“All work and no play makes Jack a dull boy.” A writer and a recovering alcoholic, Jack Torrance is on his last chance as the recently hired caretaker of the Overlook Hotel. But weird, Kubrickian shit keeps happening, and the mad visuals lead to one conclusion: this guy has a very bad case of writer’s block. The screenplay was co-written by Diane Johnson, the writer best known for the great book Le Divorce, and I’m sure she gave an authoritative perspective to Kubrick’s wild visions of writerly madness.
8. Providence (1977), directed by Alain Resnais
Do you want to know what a novelist’s mind feels like? This Resnais film does a good job of giving us a film that shows us a writer’s process. We meet aging literary lion Clive Langham, and little by little, over the course of the movie, we realize that all these scenes that make up his life — are the scenes that make up his novel. The result is beautiful and quite touching.
7. Sunset Boulevard (1950), directed by Billy Wilder
A classic of noir and Hollywood and pure, acid screenwriting, Wilder’s genius work depicts a faded silent screen star (“It’s the pictures that got small!”), played by Gloria Swanson, and her pas de deux with the unsuccessful screenwriter Joe Gillis (William Holden), who she draws into her web with promises of fame and fortune. But we start, of course, with Gillis’ body floating facedown in the pool, and Gillis’ voice on the soundtrack: “Yes, this is Sunset Boulevard, Los Angeles, California. It’s about five o’clock in the morning. That’s the Homicide Squad — complete with detectives and newspapermen. A murder has been reported…”
6. My Brilliant Career (1979), directed by Gillian Armstrong
Australia and New Zealand seem to be the countries that produce the best female-directed stories about female writers who find freedom in their work. What’s in the water down there? This Judy Davis-starrer is set in 19th century Australia, and it’s about a young woman named Sybylla, torn between two men. But, spoiler alert: she chooses something else, and becomes a writer. The result makes your heart leap.
Photo by Ben Kaller/Columbia/Kobal/REX/Shutterstock
5. Adaptation (2002), directed by Spike Jonze
This brilliant meta-comedy (something Americans are very good at when it comes to movies about writers) is about Charlie Kaufman (Nicolas Cage, wonderful) attempting to adapt Susan Orlean’s real-life book The Orchid Thief. He finds himself fighting a wicked case of writer’s block and a slovenly twin brother named Donald. Neurosis ensues, and wild comedy that involves Orlean (Meryl Streep was nominated for an Oscar for her role) and the Florida orchid thief Laroche (Chris Cooper, who did win the Oscar). Perhaps the only movie that involves a New Yorker writer doing crazy hallucinogenic drugs while also being pinpoint accurate about what goes on in most of a writer’s day (procrastination, masturbation).
4. An Angel at My Table (1990), directed by Jane Campion
A biography of the late Janet Frame, a writer from New Zealand, this stunning early film from Jane Campion is filled with her trademark eye and empathy. In three segments, Janet grows up working class, has a difficult childhood marred by shyness, and is (erroneously) diagnosed with schizophrenia and sent to a mental hospital. For the eight years she’s inside, she’s subject to electric shock therapy. Yet even while she’s away, her short stories end up published and award-winning, something that Frame hears about at the point that she’s scheduled for a partial lobotomy. She was released and would go onto become a brilliant New Zealand writer with a full career and vivid, beautiful life.
3. Wonder Boys (2000), directed by Curtis Hanson
Taking apart a great groaning bear of a second novel by Michael Chabon, Wonder Boys has Michael Douglas as Grady Tripp, a college professor and novelist stuck, magnificently, on his second novel. It depicts the long lost weekend that develops regarding some lost Marilyn Monroe-related collectibles and a dog, with Tripp’s louche agent (Robert Downey Jr.) and a promising prodigy of a student (Tobey Maguire) at his side. Very funny, and maybe one of the only movies that gets the literary life in the hub of a college fairly accurate, and accurately grubby.
2. Barton Fink (1991), directed by the Coen Brothers
The Coen brothers are merciless, hilarious gods when it comes to movies about the life of the mind, and Barton Fink may be their best and sickest work about “writer’s block” as a metaphor for blackly comic hell. With John Turturro and Coen muse John Goodman, it’s about a New York playwright (played by Turturro) who comes to Los Angeles for a chance to write in the movies. The results are surreal visions of dreams you might’ve had about 1940s Hollywood.
Photo by Spillefimkompaniet/Kobal/REX/Shutterstock
1. Reprise (2006), directed by Joachim Trier
Two young men, best friends, at a mailbox. They both have their manuscripts of their first novels in their hands. They drop them in the box with all the hope in the world. Phillip’s manuscript is accepted, and he’s instantly a literary sensation. Erik’s is rejected. From here, the story goes to places sad and surprising, as Phillip’s success doesn’t mean he can run away from his mental and emotional problems, and Erik searches, fruitlessly, for something like talent. Joachim Trier’s staggering debut is filmed with the zeal and joy of the French New Wave, and by intelligently interrogating why we create and what it does for us (the camera doing the same thing at the same time), it creates its own magic around storytelling, writers, and its collage-like portrait of the artist as a young man.