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- The Shining: "All work and no play makes Jack a dull boy."
- Barton Fink is essentially an entire movie based on this principle, down to Fink typing the exact same establishing shot and nothing else every time he sits down. Supposedly, The Coen Brothers wrote it while they were blocked writing Miller's Crossing.
- Shakespeare in Love plays with this trope. Our first shot of Will sees him busily and confidently scribbling away, and we cut to his paper to see that he's just trying out different signatures over and over. However, he does crumple up a sheet of parchment and toss it away moodily - only for it to land next to a very Hamlet-esque skull.
- Not quite a montage, but the basic imagery is well and truly incorporated into Breakfast at Tiffany's; we see the classic crumpled up balls of paper under Paul's desk as the camera pans upward.
- In Julia, Lillian Hellman goes through one while struggling to write The Children's Hour.
- At the beginning of Throw Momma from the Train, Larry just can't come up with the right word to complete the first sentence of his new novel. He struggles even harder with it after seeing his book-thieving ex-wife on The Oprah Winfrey Show.
"'The night was', 'the night was'! 'The night....' 'The night was dry, yet it was raining.' (scoffs) 'The....the...the streets were wet....but the night....was as bright....as the earrings in Margaret Donner's ears!' My God! I'M GOIN' OUTTA MY MIND!!"
- One alternate-universe Clark Kent had writer's block while writing a novel. Frustrated, he picks up the typewriter, crumples it into a ball, and hurls it through the wall of his lunar Fortress of Solitude. It smacks into a hillside miles away, which is shown to be pockmarked with craters, each containing a crumpled typewriter...
Live Action TV
- The IT Crowd, as they attempt to find a way to make the tech department more popular. (Set to the music of The A-Team.)
- Spaced has a version where Daisy stares at a blank piece of paper in the (yes) typewriter and keeps glancing at the clock, apparently seconds apart, yet every time she does an hour has passed.
- In Millennium, author Jose Chung is shown suffering from this.
- In The West Wing, speechwriting can be difficult for both Sam Seaborn and Toby Ziegler. The way the latter deals with writer's block gives good comedic fodder, as when he sets sheets of paper on fire and when he gets drunk on Air Force One trying to write a eulogy for a Republican President he loathes. There's also the pink rubber ball.
- Black Books, in the episode in which Bernard and Manny try to write a children's book, plays this one straight.
- Bleak Expectations: The second-to-last episode has Pip Bin get into a "novel-off" with Charles Dickens, wherein the two have to stay in a hotel for a year writing a novel. Pip spends most of that year drinking coffee, staring out the window, drinking more coffee, reading through the entire dictionary, drinking some more coffee... by year's end he hasn't actually written anything.
- It's not really a montage, per se, but 1776 shows an 18th-century version of the process with Jefferson's inability to write the first draft of the Declaration of Independence — right down to the discarded blank sheet.