''Daddy-Long-Legs'', written in 1912 and set at about the same time, is Jean Webster's best-known novel (not to be confused with the [[Webcomic/DaddyLongLegs webcomic of the same name]]).

Jerusha "Judy" Abbott is an orphan, having been raised in the unpleasant John Grier Home, which is run by a board of trustees. One of the trustees, whose name is unknown to her except through the pseudonym of 'John Smith,' is impressed by a humorous essay she writes and volunteers to send her to college to study writing. The only condition he places on the generous gift is that she write him regular letters to inform him of her progress, her activities, and her plans. Outside of the first chapter, which sets up the story, these letters form the entire novel. Judy catches one glimpse of her anonymous benefactor from behind, and her only impression of him is that he is very tall and thin; she therefore dubs him Daddy-Long-Legs, and begins to affectionately view him as the father she's never had.

"Daddy" and the reader follow Judy through four years of school and join her as she meets new people -- friendly Sallie [=McBride=], Sallie's good-natured brother Jimmie, snobbish Julia Pendleton, and Julia's handsome young uncle Jervis. She spends her summers on a charming farm, tries very hard to become a writer, and falls in love.

The book has received several [[TheFilmOfTheBook film adaptations]]. It was made in 1919 with Creator/MaryPickford and in 1931 with Janet Gaynor, and looser adaptations in 1935 with Creator/ShirleyTemple (that one titled ''Curly Top'') and in 1955 with Creator/FredAstaire. The 1955 version was modified to the point where it almost qualifies for InNameOnly (among other things, Judy's name is changed to Julie, possibly because the character is now French). It was adapted into two anime productions: a 1979 TV special, and, eleven years later, an installment of Anime/WorldMasterpieceTheater, ''Anime/MyDaddyLongLegs (Watashi no Ashinaga Ojisan)''. There's also a two person musical adaptation of it that's been going since 2009.

The less-well-known sequel is ''Dear Enemy'', published a few years later, in which Judy convinces her old college friend Sallie to take the helm of the John Grier Home and turn it into a warmer and kinder place. Sallie, reluctant at first, becomes very invested in the lives of the orphans, but frequently finds herself butting heads with the eponymous 'Enemy,' her nickname for the asylum's staff physician, Dr. Robin [=MacRae=].

!!This original novel contains examples of:

* AnguishedDeclarationOfLove: Judy makes one of these, sort of, when explaining to Daddy about her feelings for the man she loves. [[spoiler:She just doesn't realize they're the same person.]]
* AnimatedAdaptation: In 1990, as a part of the Anime/WorldMasterpieceTheater. It had none other than Creator/MitsukoHorie as Judy.
** The role of Judy in the Japanese-language debut of the musical was played by superstar seiyuu Creator/MaayaSakamoto.
** There is also an earlier anime adaptation of the story, a TV special made in 1979 by Creator/TatsunokoProduction. Unlike the 1990 series, the Tatsunoko version was dubbed into English and released in the United States.
* AnonymousBenefactor: Daddy
* BlackSheep: Julia's remarks about her uncle Jervis indicate that he is this to the rest of the Pendletons, as he's far less snobbish and much more genial.
%%* BunnyEarsLawyer: Jervis Pendleton.
%%* TheCasanova: Jervis again.
* EasilyForgiven: When Judy learns that [[spoiler:Jervis is Daddy Long Legs, she never takes him to task for his whole deception and jealous manipulation of her, although this can be justified since he was recovering from a serious bout of pneumonia and she was so happy.]] Averted in the musical, [[spoiler:where she takes him to task and behaves very coolly at first...for about two minutes, ''then'' she forgives him.]]
* EmbarrassingFirstName: Judy hates her real first name, Jerusha, and mentions in one letter that the matron of the John Grier Home got it from a ''tombstone'' when trying to name the abandoned infant. When she gets to college, she goes by Judy.
* EpistolaryNovel: In the original, almost the entire story is told through Judy's letters to her benefactor.
* FirstEpisodeSpoiler: In the musical only. It's not revealed until the very end of the novel that [[spoiler:Jervis is Daddy-Long-Legs, and Jerusha's benefactor]]; in the musical, however, the audience finds this out right away, after [[spoiler:Jervis himself appears on stage in the second number to tell them so]].
* TheGhost: Daddy, who is never seen [[spoiler:(or so the reader thinks)]] until Judy's very last letter.
* GirlNextDoor: Sallie [=McBride=], as well as Judy herself.
* GorgeousPeriodDress: Daddy very generously supplies Judy with money to purchase new clothes, and she gushes at length about her beautiful dresses.
* HappilyEverAfter: The last letter of each book more or less sets this up for that book's respective heroine; the sequel confirms Judy's HappilyEverAfter status.
* InnocentInaccurate: Judy doesn't know anything about Daddy, who prefers to communicate through a representative. This frustrates her, especially when his motives for a decision are unclear. Likewise in the sequel, with Sallie and the doctor; his actions at some points are a complete mystery to her, [[spoiler:because she doesn't know he's trying to deny his love for her]].
%%* LitFic
* LoveBeforeFirstSight: The original turns this trope on its head.
* MostWritersAreWriters: By the end of the original novel, Judy has published her first real story.
* MrSmith: Daddy-Long-Legs instructs Judy to address her letter to "Mr. John Smith". She dislikes such a bland pseudonym so comes up with the nickname "Daddy-Long-Legs". His real name is eventually revealed to be [[spoiler:Jervis Pendleton]].
* OrphanageOfFear: The John Grier Home is a borderline example. The kids ''did'' have what they needed to live somewhat comfortably and weren't directly abused, but they still were emotionally neglected.
%%* OrphansOrdeal:
%%* PluckyGirl: Judy
* PossessionSue: InUniverse example; at one point after reading ''{{Hamlet}}'' Judy writes about how she imagines herself as Ophelia, except she's a "sensible" Ophelia who coddles Hamlet until he's cured of his melancholy and they rule Denmark together happily and well after the king and queen die in an accident at sea.
* RewatchBonus: If you haven't figured out before the end that [[spoiler:'Daddy' is actually Jervis]], reading the book again means you can spot all the points where [[spoiler:he's clearly intensely jealous of Jimmie [=McBride=] and working to keep Judy away from him]].
* RichBitch: Julia, although she warms up enough that Judy grows to like her better.
* RomanticFalseLead: [[spoiler:Jimmie [=McBride=]]], whom Judy likes, but only as a friend. Daddy and [[spoiler:Jervis]] don't realize that it's strictly platonic.
* ScholarshipStudent: Not precisely, but Judy might as well be this. She ''does'' earn an actual scholarship during the course of the first novel.
* SingleWomanSeeksGoodMan: Averted, especially for the time period. Judy does fall in love, but her main ambition is to fulfill what she sees as her obligation to her beloved benefactor and become a real writer. This is so much her ambition that when the man she loves proposes, she turns him down! [[spoiler: Then she finds out that they're the same person, so it all works out.]]
* SpurnedIntoSuicide: Almost. After Judy rejects his marriage proposal, [[spoiler:Jervis]] -- thinking that she doesn't love him -- goes hunting in Canada and nearly dies as a result. He wasn't deliberately trying to kill himself, but he's so depressed that he has a very difficult time recovering.
%%* UnclePennybags: Jervis, to Julia.

!!The sequel, "My Dear Enemy", has the following tropes.
* TheAlcoholic: Tommy. [[spoiler: It almost kills him, and it's only Dr [=McRae=]'s PapaWolf efforts that save him. Sallie helps him out, and once they're done, they hug each other out of distress, which almost leads both of them to a LoveEpiphany.]]
* BabiesEverAfter: It's noted that Judy and [[spoiler:Jervis]] are the parents of a little girl, whom Sallie refers to as "Judy Junior."
* BrattyHalfPint: Sadie Kate, in the sequel, although in spite of her antics she's Sallie's favorite kid. Punch is more of a direct example, though he does reform.
* ButNotTooForeign: Punch's father was Italian and his mother was Irish.
* CaptainErsatz: In the sequel, [[spoiler:the doctor's situation with his wife makes him appear to be a more humane version of Rochester from ''Literature/JaneEyre''.]]
* [[ChekhovsGunman Chekhov's Gunman]]: In the sequel. Sterry, the original farmer at the John Grier Home, is let go from his position after arguing with Sallie. Later he returns and tries to get his job back, to no avail. He [[spoiler:breaks into one of the buildings to sleep at night, and accidentally leaves a candle burning...the result being that the entire orphanage burns down.]]
* DeliberatelyCuteChild: Several orphans in the sequel, little Allegra in particular.
* DisproportionateRetribution: A girl named Hattie is adopted by a rich family... and then unadopted and sent back to the orphanage under accusations of thievery. Her sin? She took a silver Communion cup from a church and kept it for herself, naively thinking it was a toy. Sallie tells this to Judy in a letter and remarks on how unfair it is for a little girl.
* {{Determinator}}: Dr. [=MacRae=] is just as stubborn as PluckyGirl Sallie is, which works very well when they're in agreement but just as often leads to them arguing.
* EpistolaryNovel: The sequel cranks this UpToEleven by being completely epistolary, without the narrative opening chapter of the original, and by being almost three times as long. It's made up of Sallie's letters to Judy, to the 'Enemy', and to Gordon Hallock, her sweetheart in Washington, D.C.
* ExecutiveMeddling: Sallie suffers this in-universe from one of the John Grier Home trustees, "Hon. Cy," as she calls him. She learns to distract him by getting his opinion on things that don't matter, and he does prove very useful to her in his own way.
* FieryRedhead: Sallie, though this is made more apparent in the sequel than in the original novel.
* FunetikAksent: In the sequel, and not unreasonably. Sallie is of Irish descent, and the doctor is of Scottish, so she tells Judy that sometimes they speak to each other in their ancestral accents. She even writes a few sentences out phonetically so Judy (and the reader) can see what she means.
* GreenEyedMonster: Gordon is insanely jealous of the doctor. [[spoiler:Not without reason, as it turns out.]]
* HappilyAdopted: A few of the orphans in the sequel, especially after [[spoiler:the fire]]. Of special note are [[spoiler: Allegra and her brothers, who are taken in by the rich man who at first only wanted to adopt Allegra and fought heatedly with Sallie since she didn't want to tear the siblings apart; after Allegra almost dies in the fire, he changes his mind and decides to take the three in.]]
* [[spoiler: HasTwoMommies: Punch is adopted by two rich ladies.]]
* HeartwarmingOrphan: Baby Allegra, in the sequel, who charms everyone -- even crotchety, un-charmable Dr. [=MacRae=].
* HollywoodFire: [[spoiler:The orphanage goes up in smoke, but thanks to their previously-instituted policy of fire drills, all the kids make it out safely. Though Dr. [=McRae=] is severely injured while trying to save Allegra.]]
* LitFic
%%* LoadsAndLoadsOfCharacters:
%%%* LongDistanceRelationship: Sallie's relationship with Gordon .
* MysteriousPast: Dr. [=MacRae=] won't talk about his, but eventually Sallie learns from his housekeeper that [[spoiler:he has a wife and daughter. The wife is institutionalized for mental problems; the doctor knew she was unstable but believed he'd be able to help her, and had to place her in the institute when not even all his care was enough; the daughter, who shows tendencies of the same kind, [[RaisedByGrandparents lives with her grandmother]] and a devoted nurse.]]
* TheNicknamer: Sallie is this for Dr. [=MacRae=], calling him not only "Dear Enemy," but also "Sandy" (a reference to his hair color) and, at least once, "Robin lad." A few others crop up irregularly too.
* NonHumanSidekick: In the sequel, Sallie's beloved Chow-Chow, Singapore.
* OrphanageOfLove: Sallie, in the sequel, is working to transform it into this.
* PluckyGirl: Sallie, once she settles into her position as orphanage superintendent.
* RescueRomance: Done with a twist. [[spoiler:Sallie explains, in the final letter of the book, that what made her realize she was in love with the doctor was when he risked his life to save Allegra from the fire, and they didn't know if he would survive.]]
** She almost had a similar epiphany (and even toys with the idea) when [[spoiler: the doctor saves Tommy from dying of alcoholic poisoning.]]
* SingleWomanSeeksgoodMan: In the sequel, Sallie [[spoiler:breaks off her engagement to Gordon rather than give up the John Grier Home ''and'' the Doctor... after she not only learns about his tragic past, but sees how much he loves the children of the orphanage]].
* SlapSlapKiss: In the sequel, [[spoiler:Sallie and the doctor]], eventually.
* SuddenlySuitableSuitor: Of a sort, in the sequel. [[spoiler:Dr. [=MacRae=] has been in love with Sallie for months, but will not allow himself to show it because of his previous tie to his wife. Her death sets him free of that obligation, but by that point, Sallie is set to marry Gordon Hallock. Once she breaks off the engagement, however... (Though to be fair, ''he'' didn't tell her right off the bat. His housekeeper could have done so, but she didn't do it either.)]]
* {{Tsundere}} : Sallie, to Gordon [[spoiler: and to Robin]].
* WhatBeautifulEyes: Punch is noted to have ''gorgeous'' eyes, apparently the prettiest ones Sallie has ever seen.