Writing is, as all of you know, a solitary, cerebral occupation. Even when you’re actually pounding on your keyboard, you’re in your head. The process of writing, the blood, sweat, and tears of it, is difficult to dramatize. Lots of characters in movies are writers, but very few films are about writing itself. Here are my favorites that capture what a writer goes through as he tries to get the story in his head down on paper.

Bullets Over Broadway (1994) comedy written by Woody Allen – A wunderkind playwright (John Cusak) is interested in creating deep Art, but he doesn’t care about entertaining an audience. The backer of the play, a gangster, wants to give his mistress a part. John is having to compromise his art to get his project made. Meanwhile, the gangster’s henchman (Chazz Palmentari) has a flare for story and starts making suggestions. It turns out he’s the real talent, and he’s willing to kill a bad actress save his play. This movie points out two creative truths. 1) Writers can be pretentious and untalented. 2) Anyone can have good ideas.

See How They Run (2020) comedic mystery written by Mark Chappell – a fictional murder mystery set around the real Agatha Christie play The Mousetrap involving all the drama around turning a hit play into a movie, including the writer fighting with the director about the script. Even more fun, the murder mystery is full of Agatha Christie tropes that connect to the play. Fun fact: The Mousetrap has been playing in the West End of London without interruption (with the exception of the lockdowns) since 1953.

Wonder Boys (2000) comedy written by Steve Kloves, based on the book by Michael Chabon – Once promising novelist Grady Tripp (Michael Douglas) doesn’t do a lot of writing in this movie, but he captures perfectly the mania of trying to live up to the reputation of your own book, and the despair and fear at being eclipsed by a younger, more talented writer.

Shakespeare in Love (1998) comedy written by Marc Norman & Tom Stoppard – Shakespeare falls in love with Viola, who is pretending to be a man so she can act. This relationship gives him inspiration to revise his latest play and turn it into Romeo & Juliet. It’s fun to see the fictional story of how he came up with one of his most famous plays.

Sweet Liberty (1986) comedy written by Alan Alda – Follows the experience of an author (Alan Alda) whose book is being made into a movie. Even though it’s non-fiction, the Hollywood folks are changing it left and right. Alan Alda struggles to keep the integrity of his book and make the screenplay good. This is an overlooked gem of a movie with great performances from Michael Cain and Michelle Pfeiffer as temperamental movie stars.

Adaption (2002) black comedy written by Charlie Kaufman – Writer Charlie Kaufman had such a difficult time figuring out how to turn the book The Orchid Thief into a movie that he wrote the screenplay about his struggle. This movie perfectly captures the turmoil when you just can’t crack the story and everyone else you know seems to be sailing along.

The Muse (1999) comedy written by Albert Brooks & Monica Johnson – Blocked screenwriter Albert Brooks hires kooky professional muse Sharon Stone to help him. She may be crazy, but there’s a method to her madness. She helps him come up with a new idea and gives his wife the confidence to start a business. If only we could all have a muse for hire on call.

Sunset Boulevard (1950) film noir written by Billy Wilder, Charles Brackett, & D.M. Marshman Jr. – Desperate and destitute screenwriter meets desperate and unhinged movie star while a sweet assistant writes her first screenplay. Sometimes being a writer is deadly.

Stranger Than Fiction (2006) comedy written by Zach Helm – IRS Agent Harold Crick (Will Ferrell) suddenly starts hearing narration and realizes he is a character in someone’s novel. What will happen if he tries to break out of the plot and falls in love?

Author’s Anonymous (2014) comedy written by David Congalton – When several dysfunctional and unpublished writers accept inexperienced Hannah (Kaley Cuoco) into their writers group, they don’t expect her overnight success. A comedy about competition and creativity.

Something’s Gotta Give (2003) romantic comedy written by Nancy Myers – Diane Keaton is a playwright who uses the heartbreak of falling in love with her daughter’s boyfriend (who is her age) to write her next hit play. The scenes of her crying her eyes out as she types are hysterical and relatable.

See How They Run (2021) – is a fictional murder mystery set around the real Agatha Christie play, The Mousetrap. It takes place in 1953 London, and we see all the drama around turning a hit play into a movie, including the writer fighting with the director about the script. Even more fun, the murder mystery is full of Agatha Christie tropes that connect to the play. Fun fact: The Mousetrap has been playing in the West End of London without interruption (except for the lockdowns) since 1953.

Paris When It Sizzles (1964) comedy written by George Axelrod – This is a mediocre movie. The fun is seeing secretary Audrey Hepburn act out all of screenwriter William Holden’s different scenarios as he tries to figure out what kind of movie to write.

Bonus: The Purple Rose of Cairo (1985) romance written by Woody Allen – is not about writing, but the fantasy of living your favorite movie. Downtrodden Depression era waitress Mia Farrow’s life is turned upside down when the romantic lead from her favorite movie steps out of the screen.

What does it say about the writing life that most of these are comedies? Comment to let me know if I left one of your favorite writing movies off the list!

---

Want more content like this? Click here to subscribe to my newsletter.