Is Jenny Prezzioso REALLY as big a brat as the girls think, or is she just a fairly stubborn girl who hates getting dirty?
Some fans feel that "Claudia and Mean Janine" should've been called "Claudia Acts Bratty to Janine" or "Janine and Mean Claudia".
Creator's Pet: Kristy's stepsister, Karen, is loved by everyone except the fandom.
Deader Than Disco: Despite being a Cash Cow Franchise in the 1990s, the series is mostly forgotten these days, probably due to Society Marches On causing its depiction of babysitting to age badly. Even when it is remembered, BSC tends to receive more criticism than praise, and all attempts to bring the characters back for a new generation of readers have failed.
Designated Villain: Janine is demonized by Claudia for... it's hard to say, her motives change randomly. Probably because Janine has the unfortunate tendency to be obnoxious (with an IQ of 196, this makes sense)
Alan Gray for Kristy; Cokie Mason for the whole BSC on occasion.
Jessi's Aunt Cecilia qualifies, at least in her first appearance in Baby-sitters' Island Adventure. She is definitely right about how an eleven-year-old, regardless of how responsible she is, should not be left in charge of an eight-year-old and a toddler for a whole weekend. She's wrong, however, in that she seems determined to blame Jessi for the matter, rather than Jessi's parents who left her in charge.
Pamela Harding in the Little Sister spin-off series is meant to be a pint-sized Alpha Bitch, but ends up coming across as this. While she does have some genuinely snotty moments, the main reason Karen started demonizing her was because in her first appearance, at Karen's sleepover party, she didn't want to eat pizza, didn't like The Wizard of Oz, and preferred to sleep in a bed over sleeping on the floor.
Ensemble Darkhorse: Shannon is very popular among members of some snark communities. Amusingly, so is background character Pete Black. Janine also has a following.
Logan is also rather popular; he even got two "Reader's Request" books narrated by him.
Andrew in the Little Sister series.
Fad Dissonance: It's pretty hilarious to read about Claudia's totally weird new friend who wears long dresses and flared jeans, both of which have come back into style since the books were published.
Family-Unfriendly Aesop: Claudia had the nerve to make a friend outside the club, so in retaliation, the other sitters scarfed her snacks, short-sheeted her bed, left mean notes around her room (one even suggesting they leave a blank one, just to mess with her head) and trash-talked her in the club notebook that's supposed to be only sitting-related. It's Claudia who is portrayed as the wrong one and has to apologize in the end.
Also, when Alan Gray is revealed as the one who's been outright harassing Kristy with his hang-up phone calls, which were because he was trying to work up the nerve to ask her out—which she accepts. Never mind that she was genuinely frightened by what was going on before she knew who was behind it. This might be one of the worst examples of stalking behavior being portrayed as positive, given that as always, the guy gets the girl.
Fan-Preferred Couple: Claudia's sister Janine and Kristy's older brother Charlie are this for many fans.
"Funny Aneurysm" Moment: In the series finale, the girls make a time capsule to be opened in seven years and each contribute a letter. In Dawn's letter, she talks about flying between California and Connecticut and remarks that maybe by the time the capsule is opened, air travel will have changed somehow. The book was published in 2000.
Hilarious in Hindsight: In Mallory and the Mystery Diary, published in 1989, Mallory complains that it feels like she's been 11 for a decade. Cut to 1999, when the books are still being published and poor Mal is still 11...
Ho Yay/Les Yay: Lesbian subtext is a popular topic of discussion among fans.
Kristy/Abby is becoming a pretty prominent pairing in BSC fanfiction.
Memetic Molester: Some snark blogs love painting the BSC as a whole as this, due to how downright creepy their love of younger kids can come across to modern readers.
National Stereotypes: The Australian family in Kristy and the Secret of Susan has the surname Hobart (the capital of Tasmania), eat vegemite, use slang that no one in Australia has used for ages (like "brekky" and "funny as a funeral"), and have to endure tons of Crocodile Dundee references.
It's probably easier to catch the Loch Ness Monster than it is to find fans of Karen Brewer.
Jessi also gets a fair amount of abuse from fans due to her lack of characterisation beyond being the Token Minority and the fact that the entire club seems obsessed with her being black. Somewhat justified given that racism would have been a huge problem in the setting (a small, predominantly white American community in the eighties): however, the series went way overboard to the point where Being Black became pretty much Jessi's defining character trait.
Snark Bait: Several blogs and online communities are devoted to snarking these books.
Unpopular Popular Character: Janine is an unpopular smart girl who has very few friends. Her sister Claudia can't stand her most of the time, and also Claudia's friends (at least in early books) tend to think she's an annoying Insufferable Genius and usually try to avoid her. However fans love her, and she's by far one of the most popular minor characters.
Jenny Prezzioso, to some extent. Every single time she's mentioned, the sitters say something mean about her or talk about how horrible she is. To be fair, Jenny is a Spoiled Brat but it's mostly due to the way her mother raised her and then again, she's four years old. For this reason, Jenny gets a lot of sympathy from fans who think she's not nearly as bad as the sitters think.
Values Dissonance: Kristy and the Secret of Susan: while it may have seemed progressive at the time, the attitude towards autism in the book has not aged well. Kristy completely oversteps her bounds and tries to shame Susan's parents about sending her to a boarding school (never mind that said school had very good professional programs for her) and tries to force Susan to make friends (VERY difficult even for mildly autistic people) by introducing her to the neighborhood children, who treat her like a freak and coerce her into playing memory games. And to top it off, the story ends with her mother happily announcing that she's having another baby and has high hopes for it being "normal" - as if she's looking to replace her "broken" child.
Combining this with Society Marches On, the entire concept of the series. Back then it wasn't weird for a twelve year old to watch someone's children. These days you'd probably get CPS called on you.
The Woobie: Just about all of the major characters get their fair share of woobification.
Mary Anne in the early books was shy, prone to tears and severely overprotected by her dad. It's also heavily implied that she suffered from depression and anxiety in later books. In a book about admitting secrets, hers is that she spent some time in therapy, and it appreciated how much it helped her.
Stacey, due to her sad backstory, being frequently hospitalized, and dealing with her parents' divorce.
Kristy, due to her dad not being around, amongst some other family problems. Taken Up to Eleven in the movie.
Abby and Anna, due to their father's death; their mother also, albeit to a lesser extent.
Although Shannon doesn't get a lot of mention, it's clear that her home life isn't exactly peachy.
As much as many fans dislike her, it's easy to feel sorry for Dawn, who can never have her family in one place.
Claudia has her moments, such as on the occasions when she feels misunderstood by her family (and isn't just being a paranoid Bratty Teenage Daughter for once) and when she can't get the grades she wants, no matter how hard she tries.
Nicky Pike has his moments, mainly when the triplets are being mean to him.
Jerkass Woobie: Karen Brewer if you really consider what she's had to live with. Her parents divorced and remarried within a year and she was apparently expected to adjust pronto despite being six years old at the time. In the earlier books at least, she spend only two weekends out of every month with her father, and he still insists on leaving her with a baby-sitter for most of that time. Then Watson and Elizabeth dropped a "surprise! We adopted a baby!" bomb on the whole family. Her behavior may be inexcusable at times, but it's hardly surprising.