Supplements with their own pages include:
Classic Chicago by Night
- Audience-Alienating Era: Under a Blood Red Moon introduced the concept of Abominations or vampire-Garou hybrids. They have since been mocked in almost all subsequent appearances. Many games ban them outright or insist that they are impossible to create.
- Base-Breaking Character: Al Capone as a vampire? Narm Charm or idiotic?
- Big-Lipped Alligator Moment: Awakening: Diablerie: Mexico is a D&D-esque dungeon-crawl to go murder a 4th generation vampire, tear out his heart, and eat it so to gain his power. To say this is thematically dissonant with the rest of the V:TM line is understating matters.
- Ensemble Dark Horse:
- Annabelle, Anita Wainwright, Critias, Damien, Erichtho, Maldavis, and many others have their own fandoms even decades after their initial publication.
- Allicia, Evelyn, Lucian, and Sullivan Dane the Vampire Hunter are favorites from Forged in Steel.
- Franchise Original Sin: A lot of the stuff which became a permanent part of the Camarilla's structure like Princes, Primogens, Sheriffs, and so on came from this book. Interestingly, it was stated in the original book to be somewhat rare.
- LGBT Fanbase: The book contained several gay, bisexual, and lesbian characters when it was still uncommon in RPGs.
- Love to Hate:
- Lodin and Balthazar were incredibly popular villains that many player characters enjoyed fighting against.
- Modius and Juggler were similarly so for Forged in Steel.
- Moral Event Horizon: Son was always described a completely evil amoral psychopath. However, his murder of the Undead Child and Morality Pet Neon after much sexually-themed torture crossed a line for many players. Given Neon was one of the most innocent and decent of all vampires in the setting, this made many players absolutely want Son to die.
- The Scrappy: Jacob Schumpeter was meant to be a Hate Sink character but the misogyny and loathsomeness of it him resulted in many fans never wanting him anywhere near their games (being a vampire who can only feed on battered women).
- Squick:
- The fact Nicolai embraced Erichtho to be his companion despite the fact he's a pre-pubescent boy.
- Also, the fact Dusable embraced Maldavis out of sexual attraction despite being her great uncle.
- Son's aforementioned murder of Neon. He lured a adolescent boy (and he really was one, being recently embraced) to his home before torturing him for weeks then drinking him dry.
- Unpopular Popular Character: Prince Modius is one of the most beloved characters in Vampire: 'The Masquerade, appearing in three separate supplements as well as two corebooks. He is also the most incredibly detested vampire in-universe with everyone thinking of him as the Butt-Monkey. He's a 7th generation Toreador and over a century old but lives in a decaying mansion in a dying city with only his enslaved childer for companion. He's also desperate for your character's approval.
- Unintentionally Sympathetic: Helena was set up to be the "Bad" one in the conflict between Menele and Helena but it comes off as a much more Gray-and-Gray Morality one than intended. Not only was Helena a victim of Domestic Abuse during her mortal years but Menele destroyed her city of Pompeii after her betrayal of Carthage. As such, she comes off as a The Woobie or at least Woobie, Destroyer of Worlds instead.
5th Edition Chicago by Night
- And You Thought It Would Fail: Despite widespread controversy at the time, its Kickstarter hit all but two of its stretchgoals and gained enough money to fund additional art as well as two completely new separate supplements.
- Big-Lipped Alligator Moment: Redwood in Let the Streets Run Red keeps a battle-ax wielding ghoul in a gimp costume as his personal enforcer. The only explanation? He got it from another Kindred.
- He's Just Hiding: Many fans thought this of Al Capone when it was revealed he was killed in the 5th Edition sourcebook. He shows up alive in The Chicago Folios.
- Jossed: The long-standing theory that Ballard was a pedophile who fed only on his own family's children for sexual enjoyment was this by Matthew Dawkins.
- Love to Hate: Kevin Jackson has already become a well-loathed villain for many campaigns as his campaign against the Anarchs and deal with the Lasombra have opened up many new games.
- Walter Nash has quickly proven a fan favorite despite (and because) he's an utter scumbag.
- Modius returns in Rusted Jungle as even more despicable and dangerous. Also staked.
- Overshadowed by Controversy: The Kickstarter had the misfortune of occurring at the same time as the Camarilla Sourcebook release, which spawned a massive controversy among the TTRPG community (using the still-ongoing terror campaign against homosexuals in Chechnya as a plot point for vampire shenanigans) and even resulted in the Chechen Government threatening to sue White Wolf Entertainment (since they claim the deadly prisons where the torture and murder is taking place are completely normal prisons). It was also the final straw from prior controversies that tied the new release with the Alt-Right and ultimately resulted in the end of White Wolf Entertainment, with it being folded into their parent company Paradox Interactive.
- Take That, Scrappy!:
- Matthew Dawkins states he had the Second Inquisition take out Jacob Schumpeter simply because he was such a loathsome piece of crap.
- Al Capone's fate was put on the chopping block for Kickstarter backers to buy since he was always a Base-Breaking Character. The fan who purchased his fate chose to keep him alive and well.
- Unexpected Character: Talley the Hound has decided to make Chicago his home.
