The members of the eponymous club often come off as cult-like.
Every single time Jenny Prezzioso is mentioned, the sitters say something negative about her. To be fair, Jenny is bratty, but it is mostly due to her young age (four) as well as the way she has been raised by her mother. This is why some fans feel that she is not as bad as the sitters think, and is instead just a fairly stubborn girl who hates getting dirty.
Some fans feel that "Claudia and Mean Janine" should have 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. Many fans think she's overused, as she is one of the kids who appears more frequently in almost every book and she's also the main character of a spinoff called Baby-Sitters Little Sister.
Janine is demonized by Claudia for bragging a bit, but this is mostly because she has an IQ of 196.
Alan Gray for Kristy; Cokie Mason for the whole BSC on occasion.
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 that 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 sleeping in a bed over sleeping on the floor. As regards The Wizard of Oz, Pamela had described it as a "baby movie" which clearly was supposed to be patronizing to all the other girls, so that was a fairly reasonable reason to dislike her.
Claudia has the nerve to make a friend outside the club, so in retaliation, the other sitters scarf her snacks, short-sheet her bed, leave mean notes around her room (one even suggesting they leave a blank one, just to mess with her head) and trash-talk her in the club notebook which is supposed to be only sitting-related. It's Claudia who is portrayed as the wrong one and has to apologize in the end.
In the second book, 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; there's also the fact that up to this point, it's been made repeatedly clear that Kristy doesn't even like Alan because he has been bothering and pranking her since (at least) fifth grade. But since "boys tease you because they like you", the harassment can be totally overlooked. This might be one of the worst examples of stalking behavior being portrayed as positive, given that as always, the guy gets the girl.
Mary Anne decides that she wants to get a drastic new haircut, and asks the other members of the BSC if they think she would look good with a short hair. They all tell her no, and are horrified when Mary Anne goes ahead and gets her hair cut. Dawn almost has a mental breakdown because Mary Anne dared to go have a father-daughter day at the mall, where she got her haircut and a new wardrobe to go with it, and the rest of the Club ignore her until she's the one to break down and apologise for not thinking of their feelings.
Fandom Nod: Overlapping with No Pronunciation Guide. In the later books, Claudia's terrible spelling is a handy way to figure out how to pronounce some of the more unusual names. She spells "Spier" "S-P-E-E-R" and "Myriah" "M-A-R-I-A," for example.
Fan-Preferred Couple: Claudia's sister Janine and Kristy's older brother Charlie are this for many fans.
Harsher in Hindsight: 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: One subplot involves Marilyn and Carolyn Arnold sneaking a look at a horror movie and getting freaked out of their minds by it, to the point where they sleep in the same room with all the lights on, tape up electrical sockets, and set up traps for "ghosts," until they watch a documentary on how the movie was made. They becomes riveted by the special effects and demonstrations and declare it the coolest thing they've ever seen. Not only does it lift their fears, it makes them into horror movie fans, and they decide they want to direct their own horror movies when they grow up. Hmmm... that sounds a lot like the biography of a pair of Canadian twin sisters who are not only horror movie directors themselves, but host their own horror-themed game show, Hellevator!
Jerkass Woobie: Karen is bratty and is disliked by the fandom, but given what she has had to deal with, her behavior is understandable. Her parents are divorced, and both remarried within a fairly short time frame. Even worse, Karen was apparently expected to adjust immediately despite being only six years old. The first time Kristy babysits her, Karen admits that they are not supposed to talk about the divorce much. In the earlier books at least, she spends only two weekends out of every month with her father, and he still insists on leaving her with a sitter for at least part of that time. Watson and Elizabeth then adopt a baby, surprising the whole family.
Dawn has garnered a rather large Hatedom in recent years. However, many saw her as being Rescued from the Scrappy Heap in Dawn Saves the Planet, where her self-importance and Soapbox Sadie attitude are deconstructed and she gets called out. This resulted in some much-needed development which toned down her negative traits considerably.
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.
Unintentionally Sympathetic: Every single time Jenny Prezzioso is mentioned, the sitters say something negative about her. To be fair, Jenny is a Spoiled Brat, but it is mostly due to her young age (four) as well as the way she has been raised by her mother. For this reason, Jenny gets a lot of sympathy from fans who think she is not nearly as bad as the sitters think.
Karen is supposed to be likable because she's intelligent, enthusiastic, and imaginative. Many fans however can't overlook her bossy behavior and how often she is an obnoxious pest.
All the main girls can come off as this depending on the book.
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.
This is the primary reason that nearly all attempts to revive the series for 21st-century readers have failed. When the books were first written and published, it was acceptable for a preteen to work as a babysitter. These days, one would have to wait until at least their late teens to take on this responsibility.
Kristy and the Secret of Susan, which was published in 1990, may have seemed progressive at the time for highlighting autism. However, the story's overall attitude towards this condition has not aged well. Susan's boundaries are completely overstepped, and she is consistently viewed in a relatively negative light. Kristy introduces Susan to the neighborhood children (who treat Susan like an outcast) in order to force her to make friends, which is very difficult even for people with milder cases of autism. Kristy tries to guilt-trip Susan's parents out of sending her to a boarding school. Worst of all, the story ends with Susan's mother hoping that her yet-to-arrive second child will be "normal", implying that she considers Susan "broken" and wants to replace her; there are even plans to name the baby "Hope" as an indicator of this exact mindset.
Claudia's new friend is treated as "totally weird" for wearing long dresses and flared jeans, but both of these articles of clothing have since come back into style.
Mary Anne's father is supposed to be seen as overprotective because he does not let her go outdoors after certain hours, even though the other sitters can stay out as late as 10pm. Her father's behavior has become more understandable in recent decades, with Free-Range Children being a thing of the past even in American suburbs. A 12-year-old being out at 10pm is much rarer now than it was in the 1980s.
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. In later books, it is heavily implied that she suffered from depression and anxiety. In a book about admitting secrets, she confesses to having spent some time in therapy, and appreciates how much it helped her.
Jessi, due to the racism she suffered in her earliest appearances. When she's talking to the Pike kids about being teased, she refuses to tell them what names she's been called, just looking tired and saying it's "Nothing as cute as 'spiders.'"
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, though this is shown 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. Heck, she usually can't even have them in one time zone.
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.