Alternative Character Interpretation: Josie Pye is supposed to be an Alpha Bitch (in her mind anyway) but her bitchy behavior is pretty minor and a few times Anne actually starts it. Plus, characters constantly go on about how awful the Pye girls are and Josie is the youngest. You have to wonder how much of her attitude is a result of being harshly judged based on her family.
Big Lipped Alligator Moment: The scene where Anne accidentally gets Diana drunk on current wine in the musical. In the book, this incident has major consequences, causing Mrs. Barry to forbid Diana from seeing Anne. In the show, however, the scene merely happens, and is never referred to again, with Mrs. Barry being more-or-less chill about the whole thing. The audience doesn't really care, though, because it's still pretty funny.
Canon Defilement: Anne of Green Gables: The Continuing Story, the third Kevin Sullivan film, is hailed as this by many fans of the book series. Unlike the first two films, which were fairly accurate to the series (for being films based on books), the third was an original film with an original script. Not only did it ignore any of the canon after "Anne of Windy Poplars," but it was set in World War I with Anne and Gilbert as newlyweds, moving the entire series forward nearly 30 years. The characters are out-of-character as a result.
First Installment Wins: Most people don't even realize that Anne of Green Gables is a series. So much emphasis is put on the first book, most people don't even know there are sequels.
Germans Love David Hasselhoff: The novel has a huge fanbase in Japan, of all places. It's theorised that the idea of a determined little individualist is just that fascinating to female Japanese culture.
Supposedly, General McArthur's wife introduced the Anne of Green Gables novels to Japan with the aim of making Japanese women more individualistic. Make of that what you will...
The fanbase in Japan is so huge, it is not uncommon to see two Japanese get married in Green Gables on Prince Edward Island. Or for the nearby inns and hotels to be filled with other Japanese tourists. Even the signs in the tourist attractions on Prince Edward Island will often have Japanese printed right under the English.
Anne of Green Gables is even popular on an academic level in Japan. It's required reading in the curricula of many schools; in fact, it's even been republished in manga/comic format for the sole purpose of encouraging more children and teenagers to read it.
Harsher in Hindsight: Killing off Gilbert in Anne of Green Gables: A New Beginning becomes this after Jonathan Crombie died.
Les Yay: Albeit largely a case of Values Dissonance — the stories being set in an era in which gushily sentimental overtones were a standard part of any female friendship — this can be read into much of Montgomery's work. Anne Shirley and Diana Barry's relationship in the first book hits pretty much every Les Yay button there is. (The 1980s TV version makes it even more obvious.)
Values Dissonance: Young Anne is celebrated specifically for being smart, creative and ambitious, so her eventual career choice — a doting mother of six — may end up being cringeworthy to some. Especially after she makes reference, as an adult, to her 'pretty fancies'.
Gilbert Lampshades this in Anne's House of Dreams, saying, after Anne points out how wasted Leslie's potential is being impoverished and stuck with her idiot husband, that some people would consider a B.A. and burgeoning established magazine writer to be "wasted" as the wife of a poor country doctor.
There are intelligent and ambitious female characters who have careers in The Blythes Are Quoted: Penelope Craig, child psychologist; Alma Winkworth, who worked in a beauty shoppe; and Susette King, sub-editor of The Enterprise. However, the last two characters are portrayed as having become disillusioned with their careers, which could be social commentary on gender inequality.
The name Diana being considered "heathenish", and the word "heathen" itself being used can come across as this.
Marilla refers to hair dying as "a wicked thing to do".
While undoubtedly well-meant, Marilla's methods for child-rearing, at least before she gets used to Anne and her particular nature, can strike the modern reader as surprisingly rigid and lacking in understanding. Her attitudes reflect both strict Presbyterian values and the Victorian notion that children should be unquestioningly respectful and obedient to their elders to the point of being self-effacing. Early on, she has no qualms about telling Anne to "hold her tongue" when she wants her to be quiet. When Anne tells off Rachel Lynde for criticizing her looks, Marilla is outraged and, while admitting that Rachel is too outspoken, insists that her being "a stranger and an elderly person and my visitor" are "very good reasons" for why Anne should have been respectful to her (despite Rachel having been disrespectful to Anne first), and is adamant that Anne apologize. (Though to her credit, her first response is to call out Mrs. Lynde on it.)
Adopting an orphan for the purpose of having more help around the house or farm seems to be considered a perfectly acceptable motivation. Even Matthew and Marilla, who fully intend to provide the child they adopt with a good home and education, are in part motivated by the idea of Matthew having the extra help that he requires. Mrs. Blewett, who almost took Anne off Marilla's hands in Green Gables also wanted help around the house, and while Marilla felt concerned about how Mrs. Blewett would treat Anne, no one questioned Mrs. Blewett seeking to take in a child to get some extra help. Today, this kind of motivation to adopt would be considered unacceptable.
"Home children" are mentioned several times throughout the series, and though mention of their being abused is treated negatively, nobody's at all surprised by it. Mary Vance is the most extreme example: the entire neighborhood knew she was being horribly abused by her "caretaker", but nobody bothered to do anything about it. This was, sadly, a real phenomenon in Canada in the 19th and 20th centuries; between the mid-1800's and the mid-1900's, thousands of children were sent (both legally and illegally) from Britain to Canada to be used as manual labor. Many children suffered horrific abuse and neglect at the hands of their adoptive families.
Anne of Avonlea features a lot of debate about teachers whipping their students; Anne is opposed to the practice, but only manages to gain Anthony Pye's respect when she finally gives in and whips him for his misbehavior (to her own discomfort).
Davy's mistreatment of his twin sister Dora would possibly be seen as bullying today, but it is often treated humorously and Anne tends to dismiss it as "boys will be boys" stuff. She only becomes upset when Davy tells her a lie.
Rilla and Kenneth Ford share one kiss before he leaves to fight in World War I, and as a result, everyone from her mother to her friends think she and Ken are engaged. Rilla is 16, by the way, to Ken's 22 or so.
That's more due to Rilla promising that she won't kiss anyone else until his return from war, rather than the actual kiss.
Rilla raises a baby, mostly by herself, from age 14. The baby's mother had died and his father was overseas fighting, so Rilla opted for taking him with her instead of letting him die. The entire scene where she brings Jims home is rather reminiscent of a child bringing home a stray kitten; her father tells her that she is on her own and that if she cannot take care of him, he will go to the orphanage. And this is just accepted by everyone around Rilla. Very hard for modern readers to swallow. She does well, aided in part by the family maid Susan and a parenting book she holds great faith in. The entire family comes to love Jims and she raises him until the age of 3-4, but no adult really offers to help beyond Susan.
French Canadians are usually portrayed as backward or comic servants, such as the wife-beating hired man Lazarus from Magic for Marigold. Marilla in Anne of Green Gables actually refers to the French hired boys who understandably quit to pursue better paying jobs in the United States as "stupid little French boys." It is assumed that the true Canada, particularly Prince Edward Island, is Anglo-Saxon and Protestant to the core, even though French settlers predated British ones by many years.
Another example of ethnic prejudice: when Anne explains that she bought the dye that turned her hair green from a peddler, Marilla comments that she has told her "never to let one of those Italians in the house! I don't believe in encouraging them to come around at all." Anne specifies that he was in fact a German Jew.