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Top 25 Movies About Writers (16 to 20)

20. The Unpublished Wino
Miles Raymond (played by Paul Giamatti) in “Sideways” (2004)
Depressed and pathetic, Miles takes his friend on a road trip through the wine country and discovers his friend’s pre-wedding plans have little to do with tasting wine and more to do with one last taste of something else. As he anxiously awaits for a phone call from his publisher, Miles continuously doubts his writing skills only to discover his true writing talent emerges in the form of one particular love letter.

19. The Bitter Songwriter
Robbie (played by Adam Sandler) in “The Wedding Singer” (1998)
OK, so Robbie may not have been the best songwriter, but there’s nothing better than an angry musical tirade about a heartless ex. His singing skills are unfortunately confined to mostly cheesy 80s weddings, but nonetheless, his less-than-creative lyrics were still hilarious:

“You don't know how much I need you. / While you're near me, I don't feel blue. / And when we kiss I know you need me too. / I can't believe I found a love that's so pure and true. / But it all was ********! / It was a god**** joke! / And when I think of you, Linda / I hope you ******* choke!”

18. The Hedonistic Magazine Writer
Raoul Duke (played by Johnny Depp) in “Fear and Loathing in Las Vegas” (1998)
Drugs have been known to ignite a creative spark in the minds of geniuses, but Duke truly takes hallucinogenic experimentations, in the name of writing, to an inconceivable level. Despite being a fictional character, it has been said that Duke was Hunter S. Thompson’s channel for retelling personal tales without the responsibility of admittance. Either way, this writer hardly leaves time for a dull moment as his elusive mind is trifled with bats, grapefruit, cocaine, eels and orgies.

17. The Archetypical LA Screenwriter
Joe Gillis (played by William Holden) in “Sunset Blvd” (1950)
A struggling Angeleno trying to land a meeting with a studio exec may be the quintessential Hollywood cliché, but few have the serendipitous befalling of accidentally driving (literally) directly into a career-saving opportunity. With all Joe’s pride and passion, he inspires desperate screenwriters by his arduous persistence and demonstration of just how far some may have to go to be successful. Shacking up with a has-been actress is not beyond the call of duty. And Joe poignantly states on behalf of screenwriters everywhere:

“Audiences don't know somebody sits down and writes a picture; they think the actors make it up as they go along.”

16. The Voyeuristic Author
Sarah Morton (played by Charlotte Rampling) in “Swimming Pool” (2003)
Writer’s block is a common ado for writer movies: character has been successful; character has impending stress on continuing to be successful; character gets too lost in her own head and needs a peaceful asylum; character searches for inspiration and gets more than she bargained for, creating some ground-breaking, atypical masterpiece. Nothing new there. But Sarah, in particular, has the rare luxury of battling her writer’s block at her publisher’s summer home in France. If only all writers had such remedies. But Sarah’s rarity and distinction as a writer is not strictly about the evolvement of her work. Her #16 ranking comes from being a complete kook and creating images in her head she is convinced are real, consisting of watching a young girl’s bizarre sexual escapades and late-night routines. Quite the adventure for this stuffy English mystery novelist, and an even better adventure for those who watch her.

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