Every week at SiftPop.com, we challenge our writers to choose what they think is the best movie under a certain topic related to a recent release. So this week, with the release of The Lost City, we’re counting down our favorite movies about writers! Let us know @SiftPop what your ranking is!

Hobbling. It’s a barbaric form of torturous control that most audiences were unfamiliar with before 1990. Though it became frighteningly understood to moviegoers in late November of that year as the squeamish act played out on the big screen in the Stephen King adaptation of the same name, Misery. The film follows a writer, Paul Sheldon (James Caan), who is the author of a successful series of Victorian romance novels featuring a character named Misery Chastain. Paul is involved in a car accident in the remote mountains of Colorado, and his rescuer, self-appointed number one fan, Annie Wilkes (Kathy Bates), takes Paul under her care due to an ensuing snowstorm that renders the roads impassable. It is quickly revealed that Annie, a former nurse-turned-cock-a-doody, obsessive fan, is enraged by Paul’s latest novel that sees the character Misery die at the end. Annie refuses to allow Paul to leave, and instead forces him to write a new novel titled, Misery’s Return. But when Annie discovers that even in his weakened condition, Paul has been secretly leaving his room, she devises an awful plan that will ensure he goes on writing, while also ensuring that he could never run away. Don’t worry, she doesn’t kill him, —“That would be like junking a Mercedes just because it had a broken spring.” No, the operation was called hobbling. Its effect was shockingly intense, unsettling body horror, the sight of which bores into the minds of any viewer. And Bates’ stellar performance earned her the Academy Award for Best Actress. “God, I love you.” (Jonathan Fedee)

I have to admit, Woody Allen is not a filmmaker whose work I pursue. In fact, I think Midnight in Paris is probably only the second film of his I ever saw, and that was only two months ago. So imagine my surprise when I found myself utterly adoring this niche little flick starring Owen Wilson in a very non-Owen Wilson like way. He plays a TV screenwriter, Gil who is putting some pressure on himself to expand his “art” and write a novel, much to the chagrin of his wife, Rachel McAdams, who wants him to stick with his cushy, well paid TV gigs. Constantly romanticizing about Paris from the days of yore, he accidentally’s himself into a time warp of some sorts and begins to navigate Paris in the 1920s on a nightly basis, meeting all of the iconic artists of that time. Midnight in Paris is beautifully romantic and captivating in ways that comfort the soul. The central message of appreciating and living in the now is the only path toward true happiness is also conveyed very, very well. (Adam Ritchie)

“All work and no play makes Jack a dull boy.” Stanley Kubrick’s movie version of Stephen King’s The Shining is a prime example of expert level horror film. The film tells the story of Jack Torrance (Jack Nicholson), a writer who gets hired as winter caretaker of the Overlook Hotel. Jack brings along his wife Wendy (Shelley Duvall) and son Danny (Danny Lloyd). This film is a slow burn that builds the tension and causes you to go insane with Jack. Kubrick’s techniques shine here, even if it is one of King’s least favorite adaptations of his work. So many modern horror movies rely too heavily on jump scares and gore, but one thing that makes this one great is how Kubrick handles the scares just right. The Shining is one of those movies you definitely need to see at least once in your life, and I highly recommend it. (Austen Terry)

Adaptation. was one of those films that I simply could not wait for. After all, I am a huge fan of Being John Malkovich, both films being directed by Spike Jonze and written by Charlie Kaufman. Adaptation. stars Nicolas Cage playing Charlie Kaufman (and Donald Kaufman) trying to write an adaptation of the book The Orchid Thief.  What makes this film great is the meta of it all. It is an actual account of Kaufman attempting to adapt The Orchid Thief into a movie. It’s a snake eating it’s own tail kind of movie that I just love, and a fantastic look in the mind of one of the modern day great screenwriters. Cage gives an amazing performance in the dual roles that makes it a must see. HINT: The film is currently on HBO Max in the U.S. You’re welcome. (Frank Kemp)

Director Rob Reiner successfully brought Stephen King’s short story “The Body” to life with his 1986 film, Stand by Me. The film is composed of some of the youngest and brightest talent of the time, which includes Wil Wheaton, River Phoenix, Corey Feldman, Jerry O’Connell, and Kiefer Sutherland. The group of friends who are featured most prominently come off natural and as if they have been buddies all their lives. Especially the strong bond shared between Gordie (Wheaton) and Chris (Phoenix), the heart-to-heart talks between these two characters are the core of the film. Wheaton and Phoenix are terrific as their respective characters and keep you immersed in the film with their on screen friendship. Teddy (Feldman) and Vern (O’Connell) provide most of the levity with their more eccentric characters. The late Phoenix is given a very complex character and does wonders through his performance, coming from a family with a bad reputation, which acts like a shadow always casted upon him. Despite his rougher exterior, he is thoughtful, especially when conversing with Gordie. Some of the best films are that of the more intimate variety; Stand by Me is one of those films. (Joe Vargas)

Let’s be honest with ourselves, yeah? Who hasn’t dreamt of following around their favorite band when they were a young kid? Heck, some people did take that path. But none did it better than high schooler William Miller (Patrick Fugit) in Almost Famous, who conned his way into getting a job writing for Rolling Stone Magazine so he could go on a nationwide tour with his favorite band, Stillwater. Queue the craziness. Whether it’s the groupies the bandmates hook up with behind their wives’ backs, the excessive drug use, all of the internal fights within the band, or the band’s plane almost crashing, there’s plenty for Will to write about for Rolling Stone. That’s not even counting Will‘s personal journey as he falls in love, learns how to relate to his mother, and has his own personal coming-of-age tale. When all is said and done, it adds up to Almost Famous being a fantastic film that deserved winning the Oscar for Best Original Screenplay, and remains a high recommendation to this day. (Heath Lynch)

This is how you update a well-worn adaptation. Coming off her directorial debut (Lady Bird), Greta Gerwig took aim at Little Women. Louisa May Alcott’s novel has seen numerous adaptations over the years, and, admittedly, I’ve neither seen any of the previous nor read the original novel. However, this version is pulled off so perfectly, it would be hard for any other to uproot it. These characters are who they are in this movie, for me. It’s clear how much of a passion project this was for not only Gerwig, but for Saoirse Ronan as Jo — even if there wasn’t a bunch of behind-the-scenes trivia to back up what you’re seeing on screen. The passion that Jo has in pursuing her dream of being a writer and getting her novel published is central to the film. It’s also where Gerwig’s tweaks to the source material really shine when it comes to the ending. It’s updated for modern audiences without crossing the line and coming off as anachronistic. Oh, well, and I suppose having your cast filled out by the likes of Emma Watson, Florence Pugh, Eliza Scanlen, Laura Dern, Timothée Chalamet, and Meryl Streep doesn’t hurt things either. (Jake Bourgeois)

What are the dangers of writing about your own experiences, especially those intimately involving others? Richard Linklater made a splash with his verbose and dialogue-driven romance, Before Sunset. Jesse (Ethan Hawke) and Celine (Julie Delpy) were just two young strangers who had a once-in-a-lifetime connection over the course of one night. The result? Jesse became a successful writer telling a “fictionalized” version of that night. Years later, they spend the late afternoon with each other. What is miraculous is that Linklater captured the same spark and delivered a fantastic sequel in Before Sunset. The characters are older, more mature, and have connections that complicate their love that is rekindled over the course of the film. This is a complex and moving cinematic experience, as it creates one of the most organic romances. Period. Hawke and Delpy sparkle together all over again; but will it last this time? This film compels all the way up to the final shot, which is moving and poignant in the best ways. Guess what? Linklater only does it again with the third (and maybe final) entry, Before Midnight. (Shane Conto)

Spotlight couldn’t have come at a better time. Nowadays, when we all consume everything online and most of us are not willing to buy newspapers anymore, Spotlight showcases what we could lose, if don’t start paying again. It shows investigative journalism — a bunch of people who won’t take no for an answer and go door to door, and make one phone call after another just to get somewhat sensible answer out of… well, anybody. And here’s the thing — this movie deserved to win that Oscar. Simply because it made us care about this topic, the newspapers. And let’s not forget the actual newspaper job isn’t that exciting, yet this movie never bores you. It’s slightly over two hours, but I can’t think of a scene I might want to drop. Tom McCarthy is underrated as a screenwriter and director, so I was happy to see him winning the Best Screenplay Oscar. And I hope one day, he gets his due for directing too, because this could have easily been one of those “important, yet boring movies” we have a lot of. He not only made this movie thrilling, he handled the subject matter (priests being relocated when accused of inappropriate things) with utmost respect. That’s another thing Spotlight got right: this could have easily turned sensational, but it never did. If you haven’t seen it since it came out, I’d recommend a rewatch. Also, it might be Rachel McAdams at her best. (Luke Burian)

Andy Bernard said in an episode of The Office. “I wish there was a way to know you were in the good old days before you’ve actually left them.” This thought is on full display for forgotten Hollywood star Norma Desmond (Gloria Swanson). Sunset Blvd is a cautionary tale of the dangers of obsessing over fame and attempting to recapture glory long past your prime. Joe Gillis (William Holden) is at the wrong place at the wrong time when he encounters Norma. Joe enters Norma’s life when they both needed each the most but for the wrong reasons. Joe as a struggling screenwriter needed someone who (he thought) would believe in him as a writer and Norma needed someone who believed in her enough to make it back to acting. It’s a toxic relationship filled with enabling and delusion. This is a recent film I crossed off my list of shame and I left it feeling like this is standard viewing for anyone trying to break into Hollywood. “Making it” and getting a series of films under your belt is one thing, but clawing your way back after the industry has passed you by is another thing entirely. You almost feel bad for Norma in the end, but it’s part of the manipulation after years being surrounded by people who like to play the game with her. (Mike Hilty)

Sideways

Have you ever been in that situation where you want to relax and talk to people as friends, but the people you are with insist on partying and trying to get some action? That’s what unpublished writer Miles Raymond (Paul Giamatti) deals with as he spends the week on a road trip with his college friend Jack Cole (Thomas Haden Church). A short way into the trip, Jack learns Miles has become acquainted with a waitress named Maya (Virginia Madsen). The implication is that Miles never intended his relationship with her to be anything more than someone to share small talk with while he’s at the restaurant where she works. Jack, however, immediately starts pushing Miles to try and make the moves on her, which makes Miles feels uneasy. Setting in motion a clear theme for the comedy throughout, Jack will lie and waste no time trying to get with any woman he finds, in this case, future Killing Eve star Sandra Oh as Stephanie. Meanwhile, Miles struggles to know how to act even when presented with a woman that’s into him. As the story progresses, Jack’s act first, think later attitude catches up with him, but Miles has to suffer to make things right. Combined with some good chemistry between Giamatti and Church, some stunning shots of Santa Barbara, and many downright hilarious sequences, this seemingly mundane story is so compelling from beginning to end. (John Tillyard)

Capote

So if I were to ask you to name a Truman in a movie, who would you guess? Well, you’d be wrong…. unless you said Truman Capote, then you’d be right. Yes, this week I decided to put on the film Capote, a film about the years Truman spent researching and writing his novel In Cold Blood. In this movie, Phillip Seymour Hoffman shows why he was one of the greats: truly disappearing into the character of Capote, as he works to learn the motives behind the killers, especially that of Perry Smith (Clifton Collins Jr.). It’s an interesting look into the life of a writer as he writes about a cold-blooded killer, while also looking for the humanity inside the man. His actions as to research the book, including to help with the appeals process, echo both someone wanting to have a set goal for themselves, but also to try to find some shred of humanity to hold onto even with the darkest of people. It also echoes the difference between himself and his friend Harper Lee (Catherine Keneer) as she has her own meteoric rise for her book To Kill a Mockingbird. It’s a fascinating look into these artists’ lives, one I can’t help but feel drawn into. (Joseph Davis)

The Disaster Artist

Tommy Wiseau genuinely thought he was making a masterpiece in The Room, which did indeed make its mark, and, one could say, became a bigger movie than it ever would have as a run-of-the-mill drama. The Disaster Artist is a funny and heartwarming film about the troubled making of The Room, starring (and directed by) James Franco as Wiseau. I’m a big proponent of separating the art from the artist, and I will confidently say that Franco does an incredible job in his various roles, especially alongside his brother Dave Franco, the latter of whom plays Greg Sestero, a struggling actor who infamously put everything on the line to help Wiseau out with The Room. Acting as an actor playing an entirely different role is not particularly easy, and both Francos are wonderfully effective. You shouldn’t throw spoons at the screen while watching The Disaster Artist, but it’s nevertheless a valuable portrait of what might be the craziest film shoot of all tim,e spearheaded by what might be the craziest filmmaker of all time. (Rowan Wood)

Moulin Rouge!

If someone were to ask me to give an example of a stylistic director, I’d point you to Baz Luhrmann, and specifically to this film — Moulin Rouge! Bright, colorful, tragic, and romantic, this is a film staged around what it is to live your life in and around the stage. As such, it comes with high-tempered emotions that cause the same to unfold in the viewing audience. So for what it is, everything about it is pitch-perfect. The cast is magnetic and full of unbalanced chemistry. The music is just phenomenal — no questions there — and the design is unparalleled. This is just a thrilling watching experience, and I highly recommend any, and all musical fans watch it at least 15 times in their life. (Alice-Ginevra Micheli)

Stranger Than Fiction

I know what you’re thinking: in 2022, when Deadpool has had two and a half movies come out, and everyone knows what it’s like to see a movie where its main character knows he’s a character, the concept doesn’t really seem all that original. And maybe it shouldn’t be an original thing, but certainly when 2006’s Stranger Than Fiction came out, Will Ferrell wasn’t exactly the kind of actor who was known to be able to play dramatic roles, either. The movie combines that concept with Ferrell’s unexpected dramatic chops very well, featuring Emma Thompson as an author who just cannot figure out how to end her novel — the novel that stars Ferrell’s character Harold Crick. Through whatever happenstance, he finds out he is indeed a character in an unfinished book, and sets out to prevent his own death at the hands of his author — somehow. With Dustin Hoffman and Maggie Gyllenhaal rounding out the main cast, Stranger Than Fiction is a movie I have some very fond memories of, and it achieves it all off the back of a very simple premise that’s executed with charm, heart, and just a little bit of absurdity. (Chris Bakker)

Ruby Sparks

Ruby Sparks is a rare movie for me where I had only ever seen it once, back about six years ago. While a lot has happened in that time, and a lot of things have passed in and out of my memory, this movie has stuck pretty strongly. Paul Dano plays Calvin, a novelist who has been cursed with early success and now has the burden of writing something new, but has no idea what that is. He begins to write about a girl that he dreams about and becomes inspired, even falling in love with the idea of this fictional idealized woman, only to find that she has been manifested in the flesh by magic. The story is written by Zoe Kazan, who plays the titular character and I absolutely love the creativity and originality. I also love the messaging it has about wanting something that we don’t truly understand and then fighting for control of it when it goes in directions we couldn’t possibly anticipate. The acting is charming and the chemistry that Dano and Kazan have is really enjoyable. It’s the perfect blend of real, with a little pinch of surreal, that allows for grounded but whimsical storytelling that triggers a consideration on how we perceive things around us and how our wants and egos affect those around us. I couldn’t recommend this movie more, and just thinking about it makes me want to rewatch in the not too distant future. (Evan Lucken)

Mank

Normally, I am not one for stuffy stories about the “great work” that filmmakers, actors, and writers do. The pride and arrogance on display seems to blind from the fact that at the end of the day, they are playing a very expensive game of make believe. But Mank has something more importance up its sleeve: a question about the relevance of one’s work and talent. Set against the backdrop of Depression-era Hollywood, Herman Mankiewicz (Gary Oldman) races against the clock to finish the screenplay for Citizen Kane. Through his process, he must find a way to channel his anger and cynicism into writing what will be considered the greatest movie of all time. Backed by a solid cast including Oldman, Amanda Seyfried, Lily Collins, and Charles Dance, our story pulls back the curtain on the wealthy and powerful. All the while, it’s laced with the directorial excellence that only David Fincher can bring to a project, we are treated to a real gem of a film. (Samuel Nichols)

Trumbo

Trumbo came as the peak of CranstonMania was on the back swing, but not before giving the man best known for playing a meth-making teacher another accolade. Nominated for an Academy Award for his role as the titular Trumbo, Bryan Cranston brings to life blacklisted screenwriter Dalton Trumbo. What I find most fascinating about this movie is the stance of the communist party in the early 1950s. I always read in history about the Red Scare and what it meant for the country, but what the history books failed to share with you is what the communist party actually believed. Cranston, at this point of his career, has proven he is a more-than-capable actor who is able to bring a range of emotions to any person who he plays, real or fictional. Trumbo has his convictions and does not waiver on his beliefs, and Cranston is able to bring that to life. What makes this the best movie about a writer is Trumbo’s journey into creating works of art to B-Movie horror flicks. Some real humor is able to be displayed as Trumbo then submits a good script that goes on to win the Academy Award for Best Story. There is so much to Trumbo that makes him a magnificent writer, and I cannot recommend this movie enough for everything that you learn not just about the man, but the unique ways in which politicians and media were able to spin stories to fit their needs. (Scott Batchelor)

Hail, Caesar!

Most of the time I hear people talking about Hail, Caesar!,they go on about how it’s one of the “lesser” films by the Coen brothers. And I don’t know whether I love old Hollywood, movies about making movies, all-star casts, or all of the above, but I think Hail, Caesar! is brilliant. Everything from Josh Brolin as the “fixer” for one of the biggest studios at the time, to Channing Tatum, who made me laugh when I wasn’t expecting it (he’s seriously an underrated comedic actor), to Scarlett Johansson worked for me. But I get it might be too “inside baseball,” where if you don’t know much about studios back in the day, the Red Scare, how screenwriters were being blacklisted just on a suspicion alone that they MIGHT be communists… This film dances (at times literally) the fine line between a comedy, mystery crime story, and almost semi-documentary about old Hollywood. Sure, have we seen movies like this before? Yes. But this is the Coens’ love letter to the cinema, to the old Hollywood, and it might be the cinephile inside me talking, but I enjoyed every single moment. And I think I need to rewatch it soon. (Luke Burian)

Fear and Loathing in Las Vegas

We all know the saying: what happens in Vegas, stays in Vegas, right? Well, Raoul Duke and his attorney, Dr. Gonzo (wildly unhinged performances by Johnny Depp and Benicio Del Toro, respectively), grab the drugs, rent a red Chevy Impala convertible and take a psychedelic journey to Las Vegas. Duke is there to write about the Mint 400 motorcycle race, but the duo has other plans in mind. They relished in the exploration of Sin City while on a drug-induced haze. Fear and Loathing in Las Vegas is such a wild, ridiculous ride. For 118 minutes, these two picked a young, hitchhiking Tobey Maguire in a balding wig, drugs, hallucinating clerks and patrons as lizards, trashing a hotel room, more drugs, trying to meet Debbie Reynolds, more drugs, having a run-in with the police while chasing the American Dream. Fear and Loathing is a mess of a film, but it’s a good mess. There’s a bit of fiction and a bit of facts, thanks to Hunter S. Thompson, whose book was adapted to give us this cult classic. (Chantal Ashford)

Also See: Barton Fink, The Player, Shakespeare in Love, Henry & June, Brigsby Bear, Secret Window, Wonder Boys, Tolkien, The Diving Bell and Butterfly, In a Lonely Place, Can You Ever Forgive Me?

If you’re interested in contributing to Best Ever Challenges or other entertainment-related articles for SiftPop, DM us on Twitter @SiftPop or email us at writersroom@siftpop.com!