History HardToAdaptWork / Literature

** ''Literature/GeraldsGame'' was long considered unfilmable considering that the plot revolves around a character trapped alone on a bed, with the narrative focusing mostly on her interior thoughts. It ultimately received [[Film/GeraldsGame a film adaption]] in 2017, 25 years after its original publication.

** ''Literature/GeraldsGame'' was long considered unfilmable considering that the plot revolves around a character trapped alone on a bed, with the narrative focusing mostly on her interior thoughts. It ultimately received [[Film/GeraldsGame' a film adaption]] in 2017, 25 years after its original publication.

* Creator/CormacMcCarthy has seen many of his works put to film, but ''Literature/BloodMeridian'' is not one of them. Even more than [=McCarthy's=] other works, ''Blood Meridian'' is [[{{Gorn}} extremely violent]], featuring countless acts of scalping, maiming, rape, and murder by ''[[VillainProtagonist its protagonists]]'' alone, presented with disturbingly gruesome banality as a scathing GenreDeconstruction of TheWestern. While there's actually very little in the way of technical challenges that could prevent a film from being shot and made (horrific violence and philosophical plot aside, nothing about the story is outwardly fanciful or inconceivable for a Western film), it's definitely "hard to adapt" by virtue of [[AudienceAlienatingPremise only attracting a very niche audience]] and inherently invoking the preemptive wrath of censors. For a character-specific example, Holden was written as a physical monstrosity that probably couldn't exist and therefore impossible to convincingly portray in live-action. In 2023, it was announced that [=McCarthy=] himself would take a crack at adapting the book into a screenplay and be an executive producer; unfortunately, [[DiedDuringProduction he died soon afterwards]], leaving the fate of the project uncertain.

** The founding work of the franchise is a downplayed example. The book chronicles Ender from ages 6 to 12 (plus an epilogue of quite a lot longer), an age when it is hard to find actors who are capable of, well, acting, much less portraying a character of any complexity. Creator/OrsonScottCard, who has a lot of experience in theatre, was adamant that the film not be made unless an actor could be found who could carry the role. Then-15-year-old Creator/AsaButterfield rose to the challenge, aided by a CompressedAdaptation that squeezes the whole story into less than a year and the casting of Creator/HarrisonFord as Col. Graff, and [[Film/EndersGame the resulting film]] was released in 2013. It didn't turn a profit, but no one complained about the acting.
** The sequels play this issue much straighter. Marvel's adaptation ''Literature/SpeakerForTheDead'' was the only book they adapted that had nothing to do with the BugWar. And it remains the only time that book got a derived work, as author Creator/OrsonScottCard deems it unfilmable, given "It consists of talking heads, interrupted by moments of excruciating and unwatchable violence." The follow-ups ''Literature/{{Xenocide}}'' and ''Literature/ChildrenOfTheMind'' can also be considered hard to adapt, being bloated philosophical works.

* ''Literature/EndersGame'': Marvel's adaptation ''Literature/SpeakerForTheDead'' was the only book they adapted that had nothing to do with the BugWar. And it remains the only time that book got a derived work, as author Creator/OrsonScottCard deems it unfilmable, given "It consists of talking heads, interrupted by moments of excruciating and unwatchable violence." The follow-ups ''Literature/{{Xenocide}}'' and ''Literature/ChildrenOfTheMind'' can also be considered hard to adapt, being bloated philosophical works.

** ''Literature/TheSilmarillion'' is less a single narrative and more a collection of smaller tales that form a somewhat cohesive historical account. Essentially, it was pieced together posthumously from a body of material Creator/JRRTolkien had worked on for much of his life, ever since ''World War I'', and the earlier-published but later-written books were practically just spin-offs of it. However, he had never managed to complete the work to his satisfaction due to his constant rewrites and additions. Most of it takes place during the First Age and the War of the Jewels and covers a period of about 600 years, switching the narrative between many different characters and dispensing ''lots'' of exposition. As such, an adaptation would be nearly incomprehensible, even to people who were familiar with ''The Lord of the Rings'', unless you were a big nerd who already studied the background. Even then, it's difficult to link to ''The Lord of the Rings'' because of the insane time differences -- to put it in perspective, the War of the Jewels was as distant from the events of the prologue of ''The Lord of the Rings'' films as said prologue is to Frodo and his adventures.

* The uncentered, interview-based structure of Max Brooks' ''Literature/WorldWarZ'' caused it to be difficult to adapt. The movie version of ''Film/WorldWarZ'' instead takes a more traditional narrative approach, focusing on a few central characters before and during the ZombieApocalypse.

** ''Literature/TheHobbit'' has had ''three'' attempts to adapt it to film, none of which were as successful as ''The Lord of the Rings''. For Tolkien, it's got a lot of EarlyInstallmentWeirdness, including talking animals, a talking ''bag'', and the existence of giants. It's so episodic that there are multiple points that could be considered a climax. Its dwarf characters are comically underdeveloped, especially compared to ''[=LoTR=]'''s protagonists. And most problematically, despite happening before ''The Lord of the Rings'' and containing several characters who appear in the later work, it's not really a prequel to ''[=LoTR=]'' -- the temptation to treat it as such is perhaps the biggest stumbling block. Creator/PeterJackson, in adapting ''The Hobbit'' to [[Film/TheHobbit film]], essentially tried to clone ''The Lord of the Rings'', making it a {{prequel}} trilogy as long as the original -- in spite of the source material being ''much'' shorter than ''The Lord of the Rings'', leading to a lot of {{Padding}}. Jackson's hand may have been forced by ExecutiveMeddling, and the ''Hobbit'' trilogy was significantly less acclaimed than ''[=LoTR=]'', but it was still a massive [[CashCowFranchise financial success]] (particularly the [[Film/TheHobbitTheBattleOfTheFiveArmies third film]]), and its [[BetterOnDVD extended editions were better received]].

* Creator/CormacMcCarthy has seen many of his works put to film, but ''Literature/BloodMeridian'' is not one of them. Even more than [=McCarthy's=] other works, ''Blood Meridian'' is [[{{Gorn}} extremely violent]], featuring countless acts of scalping, maiming, rape, and murder by ''[[VillainProtagonist its protagonists]]'' alone, presented with disturbingly gruesome banality as a scathing GenreDeconstruction of TheWestern. While there's actually very little in the way of technical challenges that could prevent a film from being shot and made (horrific violence and philosophical plot aside, nothing about the story is outwardly fanciful or inconceivable for a Western film), it's definitely "hard to adapt" by virtue of [[AudienceAlienatingPremise only attracting a very niche audience]] and inherently invoking the preemptive wrath of censors. For a character-specific example, Holden was written as a physical monstrosity that probably couldn't exist and therefore impossible to convincingly portray in live-action. In 2023, it was announced that [=McCarthy=] himself would take a crack at adapting the book into a screenplay and be an executive producer, though he died soon afterwards.

* Creator/CormacMcCarthy has seen many of his works put to film, but ''Literature/BloodMeridian'' is not one of them. Even more than [=McCarthy's=] other works, ''Blood Meridian'' is [[{{Gorn}} extremely violent]], featuring countless acts of scalping, maiming, rape, and murder by ''[[VillainProtagonist its protagonists]]'' alone, presented with disturbingly gruesome banality as a scathing GenreDeconstruction of TheWestern. While there's actually very little in the way of technical challenges that could prevent a film from being shot and made (horrific violence and philosophical plot aside, nothing about the story is outwardly fanciful or inconceivable for a Western film), it's definitely "hard to adapt" by virtue of [[AudienceAlienatingPremise only attracting a very niche audience]] and inherently invoking the preemptive wrath of censors. For a character-specific example, Holden was written as a physical monstrosity that probably couldn't exist and therefore impossible to convincingly portray in live-action.

* The ''Franchise/{{Dune}}'' universe has proven difficult to successfully adapt to the big screen due to its length, complexity, and significant amounts of [[FantasticDrug spice-induced psychedelia]]. Creator/AlejandroJodorowsky unsuccessfully attempted an adaptation of the [[Literature/{{Dune}} first book]] in the 1970s, despite first-rate talent at his disposal (documented in ''Film/JodorowskysDune''). The director's cut of Creator/DavidLynch's [[Film/Dune1984 film]] is over three hours long and still has to cover large portions of the book in narrated {{Time Skip}}s. The Creator/SciFiChannel had a little more success by adapting the first three books of the series as two separate [[Series/FrankHerbertsDune TV miniseries]], with the extra run time of a mini-series format going a long way to making the material more accessible. The [[Film/Dune2021 2021 movie]], which only adapted half the book so as to have room to breathe (a sequel will finish it off), has been very well received but is considered a bit too slavishly loyal to the book and accordingly a bit slow in some places.

* Advertisements for Creator/StanleyKubrick's 1962 film of ''Literature/{{Lolita}}'' asked "How did they ever make a movie of ''Lolita''?" It wasn't merely a catchy tagline. Not only does the novel center on a truly loathsome VillainProtagonist who lusts for his own underage stepdaughter, but it's narrated from his erudite point-of-view, [[UnreliableNarrator where he tries to paint himself as a romantic, but subtextually betrays himself as a sexual predator]]. Kubrick made his film by, among other things, slightly aging up Lolita from 12 to 14, demoting the story's most provocative content to innuendo, and softening protagonist Humbert Humbert's most heinous actions. Adrian Lynne's 1997 adaptation is TruerToTheText, but misses much of the dramatic subtext.

* ''Literature/MobyDick'' is one-fourth the story that everybody knows (a mad whaling ship captain chasing a white whale in revenge for his leg) and three-fourths an encyclopedia on whales, whaling, cetology and mythological allusions to whales. As such, almost every adaptation winds up paring down most of the {{Doorstopper}}'s content to the point where it can't really be considered the same story any more because of how ironically crucial all the background information is to the experience of reading the book. As Creator/AndrewRakich put it in his Letterboxd review of the 1998 film version, the ideal adaptation of the book would be some kind of seven-hour pseudo-documentarial miniseries about whaling in the nineteenth century with the overarching plot taking a back seat.

* ''Literature/ThePhantomOfTheOpera'' is an unfortunate example of being AdaptationOverdosed (complete with three separate high-profile adaptations in the form of an early 20th-century film, a mid-80s Broadway musical adaptation, and an early 2000s film adaptation of said musical), but yet scant few adaptations actually follow the narrative of Gaston Leroux's original book and the majority of them instead go for a distillation of the plot or just borrow similar set pieces and themes. One of the main issues of trying to get a faithful adaptation is that the novel is a horror romance thriller with a historical basis regarding the Palais Garnier opera house and trying to balance that in a different medium outside literature is difficult. This is understandably why most adaptations simply focus in on the Phantom and Christine, though this cuts into the worldbuilding of the book and does away with a sizable portion of the supporting cast, including ones who make the main characters feel more fleshed out (such as Christine's adoptive mother, Raoul's older brother, and the Persian for the Phantom). Another issue in adapting the book is the division among creators between whether it should be a chilling horror or bohemian romance. Earlier film adaptations (particularly the Creator/LonChaney film) focus mainly on horror, which takes away from the sentimentality of the novel. Later adaptations like the Creator/AndrewLloydWebber musical, on the other hand, go the opposite direction by downplaying the horror and upping the sensuality, which diminishes the threat and monstrosity the titular antagonist is supposed to embody. Additionally, much like Dracula, the reader is kept in the dark for most of the book and mainly follows the bewildered Raoul’s POV until towards the end; an approach which, while good for slow burn mystery’s purposes, is ill-suited for non-episodic adaptations. Not helping matters is that Raoul is a [[UpperClassTwit bratty]] and [[ManChild immature]] POV protagonist in the book which is why most adaptations tend to make him more traditionally competent and noble in an effort to make him more likable, though at the expense of undercutting the agency and other strong qualities of Christine (the actual main character to whom Raoul serves as a SupportingProtagonist), resulting in her becoming solely a DamselInDistress rather than a [[ViolentlyProtectiveGirlfriend protective]] heroine like she is in the novel.

* Adapting ''Literature/TheBlueLagoon'' into various forms of media such as film or theater presents a lot of complex challenges. These difficulties arise from the need to delve deeply into themes related to the growth of characters, depicting their sincerity and innocence, and accurately portraying the isolated island setting. Additionally, it is crucial to manage the passage of time, address cultural shifts, and avoid excessive sensationalism. These multifaceted issues have significantly affected the reception of film adaptations, often resulting in mixed or negative reviews. Despite having top talent at his disposal, English filmmaker Herbert Wilcox failed to successfully adapt the novel to the screen in the 1930s. Creator/FrankLaunder’s [[Film/TheBlueLagoon1949 1949 film]] had its screenplay heavily modified to comply with MediaNotes/TheHaysCode. [[Film/TheBlueLagoon1980 The 1980 film]] inevitably streamlined certain aspects of the story to make it more accessible to a wider audience, which may have left purists yearning for the intricacies and complexities found within the novel's pages.

* Adapting ''Literature/TheBlueLagoon'' into various forms of media such as film or theater presents a lot of complex challenges. These difficulties arise from the need to delve deeply into themes related to the growth of characters, depicting their sincerity and innocence, and accurately portraying the isolated island setting. Additionally, it is crucial to manage the passage of time, address cultural shifts, and avoid excessive sensationalism. These multifaceted issues have significantly affected the reception of film adaptations, often resulting in mixed or negative reviews. Despite having top talent at his disposal, English filmmaker Herbert Wilcox failed to successfully adapt the novel to the screen in the 1930s. Creator/FrankLaunder’s [[Film/TheBlueLagoon1949 1949 film]] had its screenplay heavily modified to comply with TheHaysCode. [[Film/TheBlueLagoon1980 The 1980 film]] inevitably streamlined certain aspects of the story to make it more accessible to a wider audience, which may have left purists yearning for the intricacies and complexities found within the novel's pages.

* Adapting ''Literature/TheBlueLagoon'' into different forms of media, such as film or theater, presents several complex challenges. These difficulties arise from the necessity of delving deeply into themes related to the growth of characters, depicting their sincerity and innocence, and accurately portraying the isolated island setting. Additionally, it is crucial to manage the passage of time, address cultural shifts, and avoid excessive sensationalism. These multifaceted issues have significantly affected the reception of film adaptations, often resulting in mixed or negative reviews. Despite having top talent at his disposal, English filmmaker Herbert Wilcox failed to successfully adapt the novel to the screen in the 1930s.

* Adapting ''Literature/TheBlueLagoon'' into different media, like film or theater, poses several intricate challenges. These difficulties stem from the need for a profound exploration of themes tied to the characters' growth, the portrayal of their sincerity and innocence, and the depiction of the isolated island setting. It's also imperative to handle the passage of time, address cultural shifts, and avoid excessive sensationalism. These multifaceted issues have significantly impacted the reception of film adaptations, often resulting in mixed or negative reviews. Despite having top talent at his disposal, English filmmaker Herbert Wilcox failed to adapt the novel to the screen in the 1930s.

** ''Literature/{{It}}'' has had multiple adaptations such as the [[Film/It1990 1990 Miniseries]] and [[Film/ItChapterOne 2017]]-[[Film/ItChapterTwo 2019 duology]] (the 2017 film in particular being considered very good and was a hit at the box office). However, all three works are still heavy [[CompressedAdaptation distillations]] of King's original {{Doorstopper}} whose content is an utter sensitivity minefield and MindScrew for filmmakers to adapt. The first big problem is that it is a NestedStory with the narrative split between the Losers' Club childhood ComingOfAge battle with Pennywise and them coming back to Derry OlderAndWiser and more cynical to finish Pennywise off. Not to mention the various other side stories and accounts, such as the fire at the Black Spot and drowning at the Stan Pipe, which helped flesh out the world. The Miniseries attempted to do the switching back and forth between the Losers as adults and kids, on screen however, it only makes the flow of the story cluttered and severely dampens the stakes of the childhood battle with Pennywise given the audience knows they are all going to survive to adulthood. There's also the hard task of making the adult versions of the Losers as likable and engaging as their kid selves, which the 1990 Miniseries struggled with. Unsurprisingly the 2017 film, which was solely the childhood portion got the most praise, even compared to its sequel, which featured the adult versions of the characters admirably doing their absolute best. Then there's the many content issues with the story since it involves kids being abused, killed, and most infamously having sex in a sewer and extreme racism when it comes to Mike. The Miniseries had to cut down on the violence and darker content at the cost of lessening the threat and even the DarkerAndEdgier 2017-2019 films which are even more extreme than the book in some respects -- such as Beverly's dad attempting to rape her whereas the book only implied incestuous feelings -- still had to remove the aforementioned sewer scene and the extended racial abuse Mike goes through to make it suitable for the MPAA. Finally, the CosmicHorrorStory element of the story, with Bill in the book's climax having a BattleInTheCenterOfTheMind with Pennywise in another dimension aided by Maturin the giant god turtle as ''It'' is strongly connected to ''Literature/TheDarkTower'' (see below) which is quite hard and confusing to translate on screen. This means the film adaptations are inclined to change it to just having the Losers physically kill Pennywise. Though granted the 2017 and 2019 films to their credit, touch upon Pennywise's cosmic origins and lean into the ClapYourHandsIfYouBelieve elements of the book, but still nonetheless have the Losers physically kill Pennywise and downplay or omit the elements more explicitly connected to ''The Dark Tower''.

** Several of ''Literature/TheChroniclesOfNarnia'' have been successfully adapted to screen and stage, but a notable absence is the series' third book (in chronological order; in publishing order it was the fifth) ''Literature/TheHorseAndHisBoy''. This is primarily believed to be due to how two of the main protagonists of this book are talking horses, which would be difficult to portray unironically due to how often stories featuring talking horses are usually played for comedy (such as in ''Series/MisterEd''). And even without that stigma to worry about, faithfully portraying this aspect of the story is still difficult at best due to how difficult (if not dangerous) it would be to [[NeverWorkWithChildrenOrAnimals try to train real horses]] to portray the two talking horse characters and how getting around the issue of training live horses by animating them with CGI instead would be highly expensive to use for an entire feature-length film. Tellingly, the only successful adaptation of this book was an audio play, which completely eliminated the need for any visual effects and risk of SpecialEffectFailure by relying entirely on the voice acting being heard without anyone or anything being committed to visuals.

* Adapting ''Literature/TheBlueLagoon'' into different media, like film or theater, poses several intricate challenges. These difficulties stem from the need for a profound exploration of themes tied to the characters' growth, the portrayal of their sincerity and innocence, and the depiction of the isolated island setting. It's also imperative to handle the passage of time, address cultural shifts, and avoid excessive sensationalism. These multifaceted issues have significantly impacted the reception of film adaptations, often resulting in mixed or negative reviews.
* Creator/TomWolfe's ''Literature/TheBonfireOfTheVanities'' is a [[Creator/CharlesDickens Dickensian]] satire that criticizes the excesses and social dynamics of the 1980s in a precise and cynical manner, complete with [[WorldOfJerkass a cast of jerkasses]]. Adapting the social commentary, sharp wit, and the exploration of themes such as race and class while navigating the cultural shifts since the novel's publication presents challenges for filmmakers. Creator/BrianDePalma's 1990 film adaptation had an AllStarCast of likable actors such as Creator/TomHanks [[note]]Not yet known for serious work.[[/note]] as protagonist Sherman [=McCoy=] and Creator/BruceWillis as sleazy - and in the novel, [[AdaptationalNationality British]] - journalist Peter Fallow, and bent over backwards to soften the novel's racially-charged story. The end result was a legendary BoxOfficeBomb.

* The works of Creator/HPLovecraft have a reputation for being un-cinematic. This owes in part to their being heavy on {{exposition}}, and in part to their descriptions of {{Eldritch Abomination}}s that can drive anyone who merely looks at them to insanity. The latter is difficult to put to film without being either {{Narm}}, SpecialEffectFailure, NightmareRetardant, or some combination thereof. None of this has [[LovecraftOnFilm stopped filmmakers from trying]]. A particular challenge was ''Film/{{Color Out Of Space|2020}}'', an adaptation of a story that would be [[FictionalColor unfilmable]] if it were true to the source, which chose to take advantage of the discovery of [[https://en.wikipedia.org/wiki/Magenta#In_optics_and_colour_science magenta technically being an inherently unnatural color]].

** Several of ''Literature/TheChroniclesOfNarnia'' have been successfully adapted to screen and stage, but a notable absence is the series' third book ''Literature/TheHorseAndHisBoy''. This is primarily believed to be due to how two of the main protagonists of this book are talking horses, which would be difficult to portray unironically due to how often stories featuring talking horses are usually played for comedy (such as in ''Series/MisterEd''). And even without that stigma to worry about, faithfully portraying this aspect of the story is still difficult at best due to how difficult (if not dangerous) it would be to [[NeverWorkWithChildrenOrAnimals try to train real horses]] to portray the two talking horse characters and how getting around the issue of training live horses by animating them with CGI instead would be highly expensive to use for an entire feature-length film. Tellingly, the only successful adaptation of this book was an audio play, which completely eliminated the need for any visual effects and risk of SpecialEffectFailure by relying entirely on the voice acting being heard without anyone or anything being committed to visuals.

* ''Literature/MobyDick'' is one-fourth the story that everybody knows (a mad whaling ship captain chasing a white whale in revenge for his leg) and three-fourths an encyclopedia on whales, whaling, cetology and mythological allusions to whales. As such, almost every adaptation winds up paring down most of the {{Doorstopper}}'s content to the point where it can't really be considered the same story any more because of how ironically crucial all the background information is to the experience of reading the book. As Creator/AndrewRakich put it in his Letterboxd review of the 1998 film version, the ideal adaptation of the book would be some kind of nine-hour pseudo-documentarial miniseries about whaling in the nineteenth century with the overarching plot taking a back seat.

* ''Literature/MobyDick'' is one-fourth the story that everybody knows (a mad whaling ship captain chasing a white whale in revenge for his leg) and three-fourths an encyclopedia on whales, whaling, cetology and mythological allusions to whales. As such, almost every adaptation winds up paring down most of the {{Doorstopper}}'s content to the point where it can't really be considered the same story any more because of how ironically crucial all the background information is to the experience of reading the book. As Creator/AndrewRakich put it in his Letterboxd review of the 1998 film version, the ideal adaptation of the book would be some kind of nine-hour pseudo-documentarial miniseries about whaling in the ninteenth century with the overarching plot taking a back seat.

** ''Literature/{{It}}'' has had multiple adaptations such as the [[Film/It1990 1990 Miniseries]] and [[Film/ItChapterOne 2017]]-[[Film/ItChapterTwo 2019 duology]] (the 2017 film in particular being considered very good and was a hit at the box office). However, all three works are still heavy [[CompressedAdaptation distillations]] of King's original {{Doorstopper}} whose content is an utter sensitivity minefield and MindScrew for filmmakers to adapt. The first big problem is that it is a NestedStory with the narrative split between the Losers' Club childhood ComingOfAge battle with Pennywise and them coming back to Derry OlderAndWiser and more cynical to finish Pennywise off. Not to mention the various other side stories and accounts, such as the fire at the Black Spot and drowning at the Stan Pipe, which helped flesh out the world. The Miniseries attempted to do the switching back and forth between the Losers as adults and kids, on screen however, it only makes the flow of the story cluttered and severely dampens the stakes of the childhood battle with Pennywise given the audience knows they are all going to survive to adulthood. There's also the hard task of making the adult versions of the Losers as likable and engaging as their kid selves, which the 1990 Miniseries struggled with. Unsurprisingly the 2017 film, which was solely the childhood portion got the most praise, even compared to its sequel, which featured the adult versions of the characters admirably doing their absolute best. Then there's the many content issues with the story since it involves kids being abused, killed, and most infamously having sex in a sewer and extreme racism when it comes to Mike. The Miniseries had to cut down on the violence and darker content at the cost of lessening the threat and even the DarkerAndEdgier 2017-2019 films which are even more extreme than the book in some respects -- such as Beverly's dad attempting to rape her whereas the book only implied incestuous feelings -- still had to remove the aforementioned sewer scene and the extended racial abuse Mike goes through to make it suitable for the MPAA. Finally, the CosmicHorrorStory element of the story, with Bill in the book's climax having a BattleInTheCenterOfTheMind with Pennywise in another dimension aided by Maturin the giant god turtle as ''It'' is strongly connected to ''Literature/TheDarkTower'' (see below) which is quite hard and confusing to translate on screen. This means the film adaptations are inclined to change it to just having the Losers physically kill Pennywise. Though granted the 2017 and 2018 films to their credit, touch upon Pennywise's cosmic origins and lean into the ClapYourHandsIfYouBelieve of the book.

** ''Literature/{{It}}'' has had multiple adaptations such as the [[Film/It1990 1990 Miniseries]] and [[Film/ItChapterOne 2017]]-[[Film/ItChapterTwo 2019 duology]] (the 2017 film in particular being considered very good and was a hit at the box office). However, all three works are still heavy [[CompressedAdaptation distillations]] of King's original {{Doorstopper}} whose content is an utter sensitivity minefield and MindScrew for filmmakers to adapt. The first big problem is that it is a NestedStory with the narrative split between the Losers' Club childhood ComingOfAge battle with Pennywise and them coming back to Derry OlderAndWiser and more cynical to finish Pennywise off. Not to mention the various other side stories and accounts, such as the fire at the Black Spot and drowning at the Stan Pipe, which helped flesh out the world. The Miniseries attempted to do the switching back and forth between the Losers as adults and kids, on screen however, it only makes the flow of the story cluttered and severely dampens the stakes of the childhood battle with Pennywise given the audience knows they are all going to survive to adulthood. There's also the hard task of making the adult versions of the Losers as likable and engaging as their kid selves, which the 1990 Miniseries struggled with. Unsurprisingly the 2017 film, which was solely the childhood portion got the most praise, even compared to its sequel, which featured the adult versions of the characters admirably doing their absolute best. Then there's the many content issues with the story since it involves kids being abused, killed, and most infamously having sex in a sewer and extreme racism when it comes to Mike. The Miniseries had to cut down on the violence and darker content at the cost of lessening the threat and even the DarkerAndEdgier 2017-2019 films which are even more extreme than the book in some respects -- such as Beverly's dad attempting to rape her whereas the book only implied incestuous feelings -- still had to remove the aforementioned sewer scene and the extended racial abuse Mike goes through to make it suitable for the MPA. Finally, the CosmicHorrorStory element of the story, with Bill in the book's climax having a BattleInTheCenterOfTheMind with Pennywise in another dimension aided by Maturin the giant god turtle as ''It'' is strongly connected to ''Literature/TheDarkTower'' (see below) which is quite hard and confusing to translate on screen. This means the film adaptations are inclined to change it to just having the Losers physically kill Pennywise. Though granted the 2017 and 2018 films to their credit, touch upon Pennywise's cosmic origins and lean into the ClapYourHandsIfYouBelieve of the book.

* Creator/CormacMcCarthy has seen many of his works put to film, but ''Literature/BloodMeridian'' is not one of them. Even more than [=McCarthy's=] other works, ''Blood Meridian'' is [[{{Gorn}} extremely violent]], featuring countless acts of scalping, maiming, rape, and murder by ''[[VillainProtagonist its protagonists]]'' alone, presented with disturbingly gruesome banality as a scathing GenreDeconstruction of TheWestern. While there's actually very little in the way of technical challenges that could prevent a film from being shot and made (horrific violence and philosophical plot aside, nothing about the story is outwardly fanciful or inconceivable for a Western film), it's definitely "hard to adapt" by virtue of [[AudienceAlienatingPremise only attracting a very niche audience]] and inherently invoking the preemptive wrath of censors.

** In terms of video games, the world has also seen [[TheProblemWithLicensedGames far more misses than hits]]. Adapting the events of the books presents issues; though things like length, spectacle, and large casts are less important than in a film, the books and films have long stretches of little to no action on the part of the main characters (Frodo in particular [[ActualPacifist forsakes fighting altogether by the third book]]), forcing any traditional action game to heavily modify the plot. Consequently, most of the more successful games are based primarily on the films instead. Games serving as prequels run into the issue that, while several characters do have [[ShroudedInMyth lengthy and mysterious backgrounds]], they also have obvious endpoints as characters that any prequel is going to be unable to cover. This has resulted in several attempts at [[GaidenGame side-story projects]] that take place in Middle-earth but deal with their own events, which gives the creators a lot more freedom, but also risks the final product feeling very little like Tolkien. [[ScrewedByTheLawyers Rights issues]] are also a factor; the main events and world of the books, the iconic imagery of the films, and the various other stories that Tolkien's estate [[NoAdaptationsAllowed keeps a tight grip on]] are all separate, which has created issues for quite a few developers. For instance, ''VideoGame/LordOfTheRingsTheThirdAge'' only had the rights to the films and therefore had to tightly constrain its plot to ensure the protagonists exclusively visited film locations, and ''VideoGame/LordOfTheRingsOnline'' only had the rights to the books, resulting in a noticeable off-brand look to its characters and setting.

** Several of ''Literature/TheChroniclesOfNarnia'' have been successfully adapted to screen and stage, but a notable absence is the series' third book ''Literature/TheHorseAndHisBoy''. This is primarily believed to be due to how two of the main protagonists of this book are talking horses, which would be difficult to portray unironically due to how often stories featuring talking horses are usually played for comedy (such as in ''Series/MisterEd''). And even without that stigma to worry about, faithfully portraying this aspect of the story is still difficult at best due to how difficult (if not dangerous) it would be to [[NeverWorkWithChildrenOrAnimals try to train real horses]] to portray the two talking horse characters and how getting around the issue of training live horses by animating them with CGI instead would be highly expensive to use for an entire feature-length film.