My Favorite Writing Movies

Updated June 23, 2019

Since writing mostly consists of sitting in front of a keyboard (with long moments of staring out the window thinking, “Why didn’t I listen to my mother and get a real job?” or “Should I go to the coffee shop and pretend to work there instead?”), it’s not surprising that there are few good writing movies: it’s not the most visually stimulating activity. Even so, I’ve seen a few movies that capture the writing process, or that have a deeper connection to writing and creativity.  

Stranger Than Fiction (2006) When I first considered writing fiction, I started going to readings and often heard authors talk about how characters took them in different directions. “They’re your characters,” I used to think, “Can’t you just do what you want with them?” Then I started to write myself and realized what they were talking about. This movie (featuring a wonderfully restrained performance by Will Ferrell, an actor I normally don’t like) takes this concept even further: what if your main character actually confronts you? Farrell plays an IRS agent who starts to hear someone narrating his life. He eventually discovers (after consulting with a literature professor played by Dustin Hoffman) that he’s a character in a book by an author (Emma Thompson) who’s been stuck for 10 years trying to figure out how to kill him off. He finds her and begs her not to kill him.  

Misery (1990) – Whenever I’m struggling with a scene or dealing with a particularly demanding client, I think of this movie and remind myself it could be much worse: I could be held hostage by a psycho who’s hobbled me by breaking my ankles because she didn’t like what I wrote.  

The Lives of Others (2006) and Before Night Falls (2000) – Very different movies (the former a claustrophobic film about a playwright and his girlfriend under surveillance in East Germany; the latter about a homosexual poet trying to write and survive in Castro’s Cuba), but both terrific reminders of how precious freedom of expression is, and the price many artists will pay to express themselves.  

The Wonder Boys (2000) – This quiet, precise film from Curtis Hanson (with Michael Douglas as a wonderfully frumpy college professor) picks up on many different aspects of the writing life. Douglas’s character can’t finish his book, not due to writer’s block but because he can’t stop writing. This raises great questions for writers: when is it “finished” and what is perfection in such a subjective field? It also captures the sometimes petty resentments writers can have for one another, especially successful ones, and the occasionally cutthroat world of writing classes and workshops (except for Grub Street of course!). And then there’s this great quote about the writer/editor relationship: “I sweat blood for five years and he corrects my spelling.”  

Throw Momma From the Train (1987) – Worth it if only for the scene of Billy Crystal dealing with writer’s block: “The night was…moist.”  

Adaptation (2002) –One of the few movies that illuminates the creative process, with hilarious and twisted results (as you’d expect from the combination of Spike Jonze and Charlie Kaufman). With Nicholas Cage’s wonderfully true-to-life internal dialogue, it gets into issues big and small: how does a story develop? How do different writers approach the same material? When to follow the “rules” vs. trying something new? And, of course, the whole “art vs. commerce” conundrum.   

Sideways (2004) –I like this movie not because Miles, the main character (an exquisite and nuanced performance by Paul Giametti), is a novelist but also due to the parallels it draws between wine growing and writing. Listen to Miles’s speech about why he likes pinot noir so much, replace “pinot” with “my story” and you’ll understand.  

The Shining (1980) – Let’s face it: how many writers have wanted to go mad and just take an axe to everything?  

The Squid and the Whale (2005) – The artistic temperament can have a dark and nasty side. Think of the poor behavior or personality issues of certain writers (Raymond Carver, a writer whose stories I love but whose personal behavior, even while sober, was not always the best, comes to mind). This movie picks up on some of this dark side with its offbeat, sad and occasionally disturbing look at a writing family breaking up. (Deconstructing Harry does this as well, albeit with typical Woody Allen comedy.) Bernard (Jeff Daniels) is on the downside of his fame. He’s a self-centered intellectual snob, socially inept, and so caught up in his own world that he’s lost touch with reality. In the meantime, his wife, Joan (Laura Linney), is on her way up the literary food chain. Their toxic relationship damages their two boys, one in a shocking way.

Can You Ever Forgive Me? (2018) – Along somewhat the same lines as the above, this film tells the story of Lee Israel (portrayed by Melissa McCarthy in an Oscar-nominated and occasionally squirm inducing performance), a failing writer with an abrasive personality who turned to forging letters from famous dead people. The pride she takes in her creativity in producing letters that actually could be from these people (and some of which may still be out there in collections) is the highlight here.

The Hours (2002) – An effective portrayal of how art can reflect life, this emotionally dark film looks at the impact of Virginia Wolff’s Mrs. Dalloway on three women on single days separated by almost 80 years. This includes the author herself (an Academy Award-winning role for Nicole Kidman) who we see in 1923 writing the novel, compelled to create, but slowly losing her mind in the process. Cut to 1951 where unhappy housewife Laura (Julianne Moore) loses herself in Wolff’s novel while contemplating suicide. Then fast forward to 2001 when the plot of the novel is fully repeated in the life of Clarissa Vaughn (Meryl Streep) as she plans a party for a dying former lover. A haunting reminder of how great writing is universal in time, place and meaning.  

Henry Fool (1997) – A mysterious stranger named Henry Fool appears on the doorstep of lonely, socially inept garbage man Simon Grimm. Henry presents himself as a tortured and misunderstood artist with a stack of journals he calls, “My life’s work. My memoirs. My confession.” But when he encourages Simon to write, the real artist is born: Simon writes an epic poem in one night. Considered brilliant by some, and scatological and/or pornographic by others, the poem becomes an Internet sensation. Simon, the person who looks least like a “writer,” gets a publishing deal and, several years later, the Nobel Prize, whereas Henry is exposed as an untalented hack. 

6 replies

  1. Thoughtful. I've only seen a handful of these movies. I enjoyed your pointed and brief analyses — you kept me reading.You no doubt left out, Midnight In Paris, for some reason?Gus

  2. Thanks, Gus. Yeah, Midnight in Paris was good (especially the whole issue of being happy where you are rather than longing for the past) but just seemed a bit contrived. I also left out \”You Will Meet a Tall, Dark Stranger\” as well as the writing wasn't a big element of the film.

  3. Hey Keith thanks for this list. I'm going to find a home for it in my new job as event co-ordinator for authors at The Wellesley Book Store. When you're finishing up your novel -I'm your girl! I'd love to host a book launch for you. It is a dream job & I'm thrilled with the prospect of hosting some great events! Thoughts & recommendations are welcome!

  4. I am in agreement with every film you have on your list Keith especially ‘Adaptation’ and ‘The Hours’. I was amazed by Nicole Kidman’s acting in this film especially and it was before she went and changed her whole appearance, which was a tragedy. Being a film fanatic, I watch many films especially ones that are on the edge of sanity mostly on Dish business trips. I like going to dishonline to find the more obscure films to fill my off-hour time and get on demand movies to watch in my hotel or even rentals of new movies that are interesting. I would really like to see ‘The Squid and the Whale again so I believe that I will be feasting my mind “on the dark and nasty side” tomorrow night.

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