100 Creative Writing Prompts Based on Classic Literature: A Bridge Between Literary Heritage and Modern Expression

100 Creative Writing Prompts Based on Classic Literature: A Bridge Between Literary Heritage and Modern Expression

In an age where classic literature continues to captivate and inspire, these 100 imaginative writing prompts offer a fresh approach to timeless tales. This carefully curated collection invites writers to explore the depths of beloved literary works through creative exercises that honor the original material while encouraging innovative storytelling approaches. Each prompt serves as a gateway to understanding the enduring relevance of classical literature in our contemporary world.

From Shakespeare to Shelley, Austen to Wilde, these prompts draw inspiration from literature’s most memorable characters and compelling narratives. Writers are challenged to dive deep into the psychology of classical characters, reimagining their motivations, conflicts, and revelations through exercises that range from character studies to alternative perspectives. Whether examining Frankenstein’s ethical dilemmas or Jane Eyre’s hidden narratives, each prompt opens new avenues for creative exploration.

The collection spans multiple genres and literary periods, offering diverse opportunities for writers to engage with different storytelling traditions and techniques. Gothic romance, social satire, tragedy, and epic poetry all find representation in prompts that encourage writers to examine the craft of storytelling from various angles. These exercises help writers understand how classical narrative techniques can be adapted and applied to contemporary storytelling.

Writers, educators, and literature enthusiasts will discover valuable tools for deep literary analysis and creative expression within these prompts. Each exercise is designed to challenge writers’ understanding of character development, plot structure, and thematic exploration while maintaining the integrity of the source material. The prompts serve as bridges between classical literary analysis and creative writing practice.

For students and teachers of literature and creative writing, this collection provides a structured approach to understanding and engaging with classic texts. The prompts encourage active learning through creative practice, helping writers develop their own voice while gaining deeper appreciation for literary masterworks. Whether used in classroom settings or for personal writing practice, these exercises offer meaningful ways to connect with the enduring power of classic literature.

 

100 Creative Writing Prompts Based on Classic Literature

1. Frankenstein’s Regret (Frankenstein by Mary Shelley) – Imagine you have created something that spirals out of your control. Write a letter of apology (or defiance) to your creation, explaining your actions and emotions.
2. A Lost Chapter of Gatsby (The Great Gatsby by F. Scott Fitzgerald) – Write a missing scene from The Great Gatsby from the perspective of a minor character (Myrtle, Jordan, or even the billboard of Dr. T. J. Eckleburg). What do they see that the main characters miss?
3. A Modern Scarlet Letter (The Scarlet Letter by Nathaniel Hawthorne) – In today’s world, people are still publicly shamed, though often through social media. Create a short story where a character is “marked” in a modern way for a past mistake. How do they cope with or fight against it?
4. Hamlet’s Dilemma in the Digital Age (Hamlet by William Shakespeare) – Hamlet struggles with indecision and overthinking. Rewrite the famous “To be or not to be” soliloquy as if he were debating his choices in a long-winded text message to a friend.
5. The Other Side of the Story (Pride and Prejudice by Jane Austen) – Retell a scene from Pride and Prejudice through the eyes of a character who isn’t Elizabeth or Darcy. How does Mr. Collins feel about being rejected? What does Charlotte Lucas think about her decision to marry him?
6. Rochester’s Hidden Letters (Jane Eyre by Charlotte Brontë) – Write the unsent letters Rochester composed to Jane during their separation, revealing his thoughts about his past decisions and his first wife.
7. The Mad Woman’s Diary (Jane Eyre by Charlotte Brontë) – Create diary entries from Bertha Mason’s perspective, describing her journey from Jamaica to Thornfield Hall and her descent into madness.
8. The Ghost of Catherine’s Choice (Wuthering Heights by Emily Brontë) – Write Catherine’s thoughts as a ghost, watching the consequences of her choice between Heathcliff and Edgar unfold over the years.
9. Marley’s Warning (A Christmas Carol by Charles Dickens) – Write the conversation between Marley’s ghost and other deceased businessmen in the afterlife as they debate who should warn Scrooge and how.
10. The Player Queen’s Revenge (Hamlet by Shakespeare) – Create a monologue from the perspective of the Player Queen from the play-within-a-play, revealing her own thoughts about Gertrude’s hasty remarriage.
11. Lady Macbeth’s Childhood (Macbeth by Shakespeare) – Write a scene from Lady Macbeth’s youth that hints at how she became the ambitious and ruthless woman we know.
12. The Green Light’s Perspective (The Great Gatsby by F. Scott Fitzgerald) – Compose a series of observations from the green light at the end of Daisy’s dock, witnessing Gatsby’s nightly vigils and the events that unfold.
13. Miss Havisham’s Wedding Morning (Great Expectations by Charles Dickens) – Write the hours leading up to Miss Havisham receiving the letter that would change her life, from her excitement to the moment of devastation.
14. The Portrait’s Secret (The Picture of Dorian Gray by Oscar Wilde) – Create an account from the perspective of the portrait itself, describing how it feels to absorb Dorian’s sins and watching him descend into depravity.
15. Elizabeth’s Modern Instagram (Pride and Prejudice by Jane Austen) – Write Elizabeth Bennet’s Instagram posts and stories during key moments of the novel, including her reactions to Darcy, Wickham, and her sisters’ adventures.
16. The White Whale’s Tale (Moby Dick by Herman Melville) – Compose Moby Dick’s own account of why he hunts those who hunt him, and his thoughts about Ahab’s obsession.
17. Watson’s Unwritten Cases (Sherlock Holmes by Arthur Conan Doyle) – Write about a case Watson never published because it revealed too much about Holmes’s human side or vulnerabilities.
18. The Three Witches’ Group Chat (Macbeth by Shakespeare) – Create a modern group chat between the three witches as they plot and discuss Macbeth’s fate, complete with memes and emoji reactions.
19. Ophelia’s Letters to Her Mother (Hamlet by Shakespeare) – Write the letters Ophelia might have written to her deceased mother, describing her feelings about Hamlet and the chaos at court.
20. The March Sisters’ Podcast (Little Women by Louisa May Alcott) – Script an episode of a podcast hosted by the March sisters, where they discuss their dreams, creative pursuits, and family dynamics.
21. Jekyll’s Dating App Profile (Dr. Jekyll and Mr. Hyde by Robert Louis Stevenson) – Create both Jekyll and Hyde’s dating app profiles, showing how each would present themselves to potential matches.
22. The Beast’s Library Books (Beauty and the Beast) – Write the Beast’s library check-out history and his margin notes in various books as he transforms from beast to man.
23. The Pepper Ghost’s Blog (A Christmas Carol by Dickens) – Write the Ghost of Christmas Past’s blog post about their most challenging cases, with Scrooge featured as a particularly difficult but rewarding subject.
24. Mrs. de Winter’s TikTok (Rebecca by Daphne du Maurier) – Create a series of TikTok posts from the second Mrs. de Winter as she navigates life at Manderley and the shadow of Rebecca.
25. Prospero’s Spellbook Comments (The Tempest by Shakespeare) – Write Prospero’s notes and annotations in his book of magic, including his thoughts about using his powers and eventually giving them up.
26. Mercutio’s Last Tweet (Romeo and Juliet by Shakespeare) – Write Mercutio’s social media feed leading up to his fatal duel, including his witty observations about Verona’s feuding families and Romeo’s lovesickness.
27. The Red Room’s Security Footage (Jane Eyre by Charlotte Brontë) – Write a modern security guard’s report of reviewing footage from the infamous red room, where young Jane was locked up, and the unexplainable events they witness.
28. Gregor’s Work Email (The Metamorphosis by Kafka) – Compose the email chain between Gregor Samsa and his employer on the morning of his transformation, as he tries to explain his absence without revealing the truth.
29. The Looking Glass Support Group (Alice in Wonderland by Lewis Carroll) – Write minutes from a support group meeting for characters who’ve fallen through mirrors, portals, and rabbit holes, sharing their experiences of returning to normal life.
30. Dorian Gray’s Influencer Apology (The Picture of Dorian Gray by Oscar Wilde) – Create Dorian’s YouTube apology video script after his followers notice he never seems to age in his photos and demand answers.
31. Lenina’s Dating App Experience (Brave New World by Aldous Huxley) – Write Lenina’s dating app conversations as she tries to explain her world’s relationship customs to modern matches.
32. The Second Mrs. Bluebeard (Bluebeard by Charles Perrault) – Write the story of the wife before the final wife – the one who almost escaped but didn’t. What did she discover, and what warnings did she try to leave?
33. Cordelia’s Family Therapy Session (King Lear by Shakespeare) – Script a family therapy session where Cordelia and her sisters discuss their father’s demand for public declarations of love.
34. The Ghost of Banquo’s Yelp Reviews (Macbeth by Shakespeare) – Write Banquo’s ghost’s reviews of various feast halls and banquets he’s haunted, with special attention to his experience at Macbeth’s infamous dinner party.
35. Miss Havisham’s Home Renovation Show (Great Expectations by Charles Dickens) – Create a transcript of a home renovation show where experts try to convince Miss Havisham to finally clean up Satis House and move on.
36. Captain Ahab’s LinkedIn (Moby Dick by Herman Melville) – Write Ahab’s professional profile, job history, and recommendations from crew members who survived his obsessive quest.
37. The Three Sisters’ Weather App (Macbeth by Shakespeare) – Design the witches’ meteorological app that predicts both weather and fate, including user reviews and glitch reports.
38. Nancy Drew Investigates Thornfield (Jane Eyre meets Nancy Drew) – Write the opening chapter of Nancy Drew investigating the mysterious happenings at Thornfield Hall before Jane’s arrival.
39. The Ghost of Christmas Future’s Memoir (A Christmas Carol by Dickens) – Write an excerpt from the ghost’s memoir about the challenges of showing people their potential futures without speaking a word.
40. Lady Macbeth’s Cleaning Blog (Macbeth by Shakespeare) – Create Lady Macbeth’s viral blog post about removing stubborn stains, with a comment section full of concerned readers.
41. Poe’s Real Estate Listings (Edgar Allan Poe’s works) – Write real estate listings for the House of Usher, the premises from The Tell-Tale Heart, and other Poe locations, attempting to put a positive spin on their haunted histories.
42. Dear Werther’s AI Therapist (The Sorrows of Young Werther by Goethe) – Script a conversation between Werther and an AI therapist as he processes his unrequited love for Charlotte.
43. The Little Match Girl’s GoFundMe (The Little Match Girl by Hans Christian Andersen) – Write the description and updates for a crowdfunding campaign to help the little match girl, started by a passing stranger.
44. Long John Silver’s Recipe Blog (Treasure Island by Robert Louis Stevenson) – Create a post from Silver’s cooking blog, where he shares recipes from his pirating days while dropping hints about hidden treasures in the comment replies.
45. Heathcliff’s Property Development Plans (Wuthering Heights by Emily Brontë) – Write Heathcliff’s proposal to turn Wuthering Heights and Thrushcross Grange into a gothic tourism experience, complete with scheduled hauntings by Catherine’s ghost.
46. Gulliver’s Travel Vlog (Gulliver’s Travels by Jonathan Swift) – Create a series of video transcripts where Gulliver attempts to monetize his bizarre travel experiences, complete with sponsorship deals for giant-sized products.
47. The Phantom’s Spotify Playlist (The Phantom of the Opera by Gaston Leroux) – Write the Phantom’s commentary on his carefully curated playlist, explaining why each song reminds him of Christine.
48. Dr. Frankenstein’s Ethics Committee Hearing (Frankenstein by Mary Shelley) – Script the proceedings of a modern university ethics committee reviewing Victor Frankenstein’s research proposal.
49. Tom Sawyer’s Community Service Blog (The Adventures of Tom Sawyer by Mark Twain) – Write Tom’s mandatory blog posts about his fence-painting scheme as part of his punishment for manipulating others.
50. The Wife of Bath’s Dating Show (Canterbury Tales by Chaucer) – Create a transcript from a reality dating show where the Wife of Bath helps modern women navigate relationships, drawing from her extensive marriage experience.
51. Count Dracula’s Airbnb Reviews (Dracula by Bram Stoker) – Write reviews from guests who’ve stayed at Dracula’s castle, along with his carefully worded responses to their concerns about the odd noises and mysterious disappearances.
52. Emma Woodhouse’s Matchmaking App (Emma by Jane Austen) – Design Emma’s pitch for a new AI-powered matchmaking app, including her defense of why her algorithm would work better than human intuition.
53. The Weird Sisters’ Weather Channel (Macbeth by Shakespeare) – Script a weather forecast show hosted by the three witches, mixing meteorological predictions with prophecies about viewers’ fates.
54. John Proctor’s Reddit Post (The Crucible by Arthur Miller) – Write Proctor’s anonymous Reddit post asking for advice about his affair with Abigail and the brewing witch hysteria, with responses from the community.
55. Mrs. Bennet’s Mommy Blog (Pride and Prejudice by Jane Austen) – Create a blog post where Mrs. Bennet shares her tips for marrying off five daughters in a difficult economic climate.
56. The Ancient Mariner’s Eco-Activism (The Rime of the Ancient Mariner by Coleridge) – Write the mariner’s speech at a climate change conference, using his experience with the albatross to warn about environmental destruction.
57. Captain Nemo’s Tech Review (20,000 Leagues Under the Sea by Jules Verne) – Create Nemo’s detailed review of modern submarine technology, comparing it to his beloved Nautilus.
58. Rosencrantz & Guildenstern’s Group Text (Hamlet by Shakespeare) – Write the text messages between Rosencrantz and Guildenstern as they try to figure out what’s really going on with Hamlet.
59. Jekyll & Hyde’s Therapy Notes (Dr. Jekyll and Mr. Hyde by Stevenson) – Write a therapist’s session notes trying to treat Jekyll/Hyde for dissociative identity disorder in a modern setting.
60. The White Rabbit’s Time Management Seminar (Alice in Wonderland by Carroll) – Script the White Rabbit’s motivational speech about overcoming chronic lateness, while continuously checking his watch.
61. Caliban’s Nature Documentary (The Tempest by Shakespeare) – Write Caliban’s narration of a documentary about Prospero’s island, focusing on the magical ecosystem he knew before the colonizers arrived.
62. Don Quixote’s True Crime Podcast (Don Quixote by Cervantes) – Create a transcript where Don Quixote investigates “crimes” committed by windmills and sheep, with Sancho Panza as his reluctant co-host.
63. The Mad Hatter’s Startup Pitch (Alice in Wonderland by Carroll) – Write the Mad Hatter’s pitch to investors for an endless tea party subscription service, including his unorthodox business model.
64. Bottom’s TikTok Fame (A Midsummer Night’s Dream by Shakespeare) – Create a series of TikTok post descriptions documenting Bottom’s viral fame after his mysterious transformation, including his attempts to recreate the experience.
65. The Walrus & Carpenter’s Food Review (Through the Looking Glass by Carroll) – Write their controversial restaurant review that led to them being banned from seafood criticism, with responses from the oyster community.
66. The Yellow Wallpaper’s Interior Design Blog (The Yellow Wallpaper by Charlotte Perkins Gilman) – Write a series of increasingly disturbing home decoration posts as the narrator reviews different wallpapers while documenting her “rest cure.”
67. Nurse Ratched’s Employee Review (One Flew Over the Cuckoo’s Nest by Ken Kesey) – Create Nurse Ratched’s annual performance review, including complaints from patients and her detailed justification of her methods.
68. The Cheshire Cat’s Self-Help Book (Alice in Wonderland by Carroll) – Write the introduction to the Cat’s bestselling book “The Power of Disappearing: How to Leave Nothing But a Smile Behind.”
69. The Raven’s Twitter Feed (Edgar Allan Poe’s The Raven) – Create the Raven’s Twitter thread documenting his nightly visits to the narrator, with increasingly ominous “nevermore” variations.
70. Robinson Crusoe’s Survival Channel (Robinson Crusoe by Daniel Defoe) – Script Robinson Crusoe’s YouTube tutorials about island survival skills, with Friday adding corrections in the comments section.
71. The Three Bears’ Property Dispute (Goldilocks and the Three Bears) – Write the legal briefing for the bears’ lawsuit against Goldilocks, including property damage claims and emotional distress.
72. Miss Muffet’s Spider Relations Committee (Little Miss Muffet) – Create minutes from the first meeting of the Human-Arachnid Relations Committee, formed to prevent future curds-and-whey incidents.
73. Kafka’s HR Department (The Metamorphosis by Kafka) – Write the internal HR emails discussing how to handle Gregor Samsa’s transformation under modern workplace accommodation laws.
74. Sherlock’s Cold Case Podcast (Sherlock Holmes by Conan Doyle) – Script the pilot episode of Holmes’s podcast where he solves historical cold cases using deductive reasoning.
75. Medusa’s Beauty Channel (Greek Mythology) – Create Medusa’s controversial beauty tutorial about achieving the perfect stone-cold look, addressing the backlash from viewers turned to stone.
76. Anne Elliot’s Second Chance Dating Guide (Persuasion by Jane Austen) – Write Anne’s viral article about reconnecting with old flames, using her experience with Captain Wentworth as a case study.
77. The Little Prince’s LinkedIn (The Little Prince by Antoine de Saint-Exupéry) – Design the Little Prince’s professional profile, listing his experiences on different planets as unique consulting opportunities.
78. The Headless Horseman’s Motorcycle Blog (The Legend of Sleepy Hollow by Washington Irving) – Write the Horseman’s review of modern motorcycles compared to his traditional horse, discussing the challenges of riding while headless.
79. Jay Gatsby’s Party Planning Service (The Great Gatsby by Fitzgerald) – Create Gatsby’s business proposal for an exclusive event planning service, promising to make every client feel as important as Daisy.
80. The March Sisters’ Podcast Network (Little Women by Alcott) – Write show descriptions for each March sister’s podcast: Jo’s storytelling hour, Amy’s art reviews, Beth’s quiet music appreciation, and Meg’s domestic life updates.
81. Scheherazade’s Substack (One Thousand and One Nights) – Create the welcome post for Scheherazade’s subscription newsletter promising a new cliffhanger story every night.
82. The White Witch’s Winter Retreat (The Lion, the Witch and the Wardrobe by C.S. Lewis) – Write the White Witch’s promotional materials for her “Eternal Winter Wellness Resort” in Narnia, addressing concerns about the “always winter, never Christmas” policy.
83. Captain Hook’s Anti-Crocodile Campaign (Peter Pan by J.M. Barrie) – Create Hook’s crowdfunding campaign to implement clock-free zones in Neverland, citing personal trauma.
84. The Little Mermaid’s Environmental Blog (The Little Mermaid by Hans Christian Andersen) – Write the original Little Mermaid’s passionate post about ocean pollution and the true cost of trading your voice for human development.
85. Dr. Moreau’s Research Grant Application (The Island of Dr. Moreau by H.G. Wells) – Write Dr. Moreau’s carefully worded grant application for his “evolutionary acceleration studies,” attempting to sidestep ethical concerns.
86. Prospero’s Magic App Reviews (The Tempest by Shakespeare) – Write Prospero’s increasingly frustrated reviews of modern magic apps, explaining why they’re no substitute for his drowned books.
87. The Boy Who Cried Wolf’s PR Crisis (Aesop’s Fables) – Create a PR firm’s strategy document for rehabilitating the boy’s image, including social media damage control and community trust-building initiatives.
88. The Byronic Hero Support Network (Lord Byron’s works) – Script a group therapy session for Byronic heroes like Manfred and Childe Harold, discussing their struggles with brooding and social isolation.
89. The Tin Man’s Wellness Journey (The Wizard of Oz by L. Frank Baum) – Write the Tin Man’s viral article about emotional intelligence and the dangers of suppressing feelings, even after getting his heart.
90. The Seven Dwarfs’ Mining Startup (Snow White) – Create the dwarfs’ pitch deck for their ethically sourced diamond mining company, addressing concerns about workplace diversity and whistle-while-you-work policies.
91. Falstaff’s Bar Reviews (Shakespeare’s Henry IV) – Write Falstaff’s Yelp reviews of every tavern in London, with detailed notes on wine quality and credit policies.
92. The Black Cat’s Exposé (Poe’s The Black Cat) – Write an investigative journalism piece from the cat’s perspective, revealing the truth about unreliable narrators in gothic literature.
93. Rapunzel’s Hair Care Empire (Rapunzel) – Create Rapunzel’s business plan for a natural hair growth company, including testimonials from princes who’ve climbed her hair.
94. Faust’s Contract Review (Faust by Goethe) – Write a modern lawyer’s analysis of Faust’s contract with Mephistopheles, pointing out potential loopholes and questionable clauses.
95. The Lilliputian Tourism Board (Gulliver’s Travels by Swift) – Design a tourism campaign for Lilliput, addressing concerns about giant visitors while promoting their miniature attractions.
96. Tiresias’s Psychic Review Blog (Greek Mythology) – Write Tiresias’s reviews of modern fortune-telling services, drawing from their experience as both male and female, mortal and prophet.
97. Odysseus’s Navigation App (The Odyssey by Homer) – Create Odysseus’s feedback on a beta version of a navigation app, detailing its performance against sirens, cyclops, and divine intervention.
98. The Good Samaritan’s Ethics Column (Biblical Parable) – Write the Good Samaritan’s advice column addressing modern moral dilemmas about helping strangers.
99. The Emperor’s Fashion Startup (The Emperor’s New Clothes) – Write the Emperor’s launch announcement for his “visionary” fashion tech company, promising clothes visible only to the innovative.
100. The Elves’ Labor Union (The Elves and the Shoemaker) – Create the founding document of the Magical Laborers Union Local #815, addressing night work conditions and proper credit for craftsmanship.

 

These 100 writing prompts showcase the immortal essence of classic literature, demonstrating how timeless narratives can be meaningfully adapted for contemporary audiences. By reimagining iconic characters and pivotal moments through a modern lens, writers can explore the intersection between literary heritage and contemporary culture, revealing new dimensions of these beloved works while maintaining their fundamental power.

Through exercises that translate classical narratives into contemporary formats—from Captain Ahab’s LinkedIn recommendations to Dorian Gray’s viral apology video—writers discover how universal themes transcend time periods and storytelling mediums. These prompts reveal that core human experiences of love, ambition, redemption, and betrayal remain powerfully relevant whether expressed through traditional prose or modern digital platforms.

For educators and students alike, these prompts serve as dynamic tools for literary engagement and creative exploration. When learners transform classical texts into familiar modern formats—imagining Ophelia’s unsent text messages or Lady Macbeth’s cleaning blog—they develop deeper connections with these enduring works. This innovative approach makes classical literature more accessible and relevant, helping students recognize the continued significance of these foundational texts in understanding human nature.

Creative writers will discover that these prompts offer more than mere writing exercises; they provide a framework for mastering character development, voice consistency, and perspective across different storytelling formats. Each prompt challenges writers to maintain a character’s essential nature while adapting their expression to contemporary contexts, developing crucial skills in narrative craft and character authenticity.

In our rapidly evolving digital world, these creative reinterpretations illuminate how classic literature continues to offer insights into contemporary human experience. These prompts demonstrate that while communication methods may evolve, the fundamental aspects of storytelling—compelling characters, universal conflicts, and profound themes—remain constant across centuries. Through this collection, writers are invited to participate in the ongoing dialogue between literary tradition and modern expression, ensuring these timeless tales continue to resonate with new generations of readers and writers.