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When Played for Laughs, there is almost always a sequence where the writer several times puts a sheet into the typewriter, types a few words, and pulls it out to crumple and throw away, followed by putting a new sheet in, staring at the blank paper for a moment, then pulling it out, crumpling it and throwing it away.
Generally a Discredited Trope nowadays -- despite that, aside from the outdated typewriter and the fact that not all writers smoke, the basic idea is close to Truth in Television, right down to the inability to leave the desk before finishing that blasted paragraph just right.
- 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 in the film version; we see the classic crumpled up balls of paper under Paul's desk as the camera pans upward.
- 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 Repuplican President he loathes.
- Black Books, in the episode in which Bernard and Manny try to write a children's book, plays this one straight.
- In FoxTrot, Roger wants to write a novel. There are a few strips where he's struggling to come up with an idea and Andy gets annoyed at how long he's taking, and then he names the trope Her Codename Was Mary Sue (not literally, but he writes the Trope Namer).
- 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.