Author's Saving Throw: There was a Second Edition sourcebook called Dirty Secrets of the Black Hand which proved very unpopular because it suggested that the Sabbat (Already a secret vampire conspiracy to control humanity) was itself controlled by a secret conspiracy within the Sabbat's "Black Hand" faction, which was itself called the Black Hand. This "True Black Hand" controlled everything from the land of the dead, residing in the ghost of the First City mankind founded. There are more details, but things only get more needlessly complicated and stupid from there. When the next edition of Vampire: The Masquerade came out, they scaled back the bloodlines introduced in that book to about a dozen members each, declared that the scope of the "True Black Hand"'s power and agenda were extremely exaggerated, and then dropped a ghost atomic bomb on the underworld city they were operating out of for good measure.
The True Black Hand got brought back in V20, scaling back their ability to influence events, retconning certain of their more egregious aspects so they were more appropriate to the setting and/or optional, and showing that the truth of many of the potentially setting-shaking secrets they were sitting on was unclear even to them.
Virtually everything in the first edition and early second edition concerning the Romani was deeply racist. Later on, the collaboration between the Romani and the Gangrel would be retconned; the founder of Romani-stereotype Clan Ravnos was blasted to flinders from orbit and most of the rest of the clan wiped out in the space of a week. Problem solved?
Complete Monster: Sascha Vykos, born Myca Vykos, is a monster whose legacy dates back to 11th Century Constantinople. Sired by the Tzimisce Symeon, Vykos eventually destroyed his sire by repeatedly consuming and regurgitating him before a final act of draining him to death. Removing his gender and taking the name "Sascha," Vykos became a major figure in the monstrous Sabbat, feared even by its monstrous Clan. Vykos invents new tortures, having perfected them upon countless unwilling victims whose agony it can prolong for years to centuries, alternating it with incredible pleasure to make the victim unsure if they're experiencing torture or rape. In modern times, Vykos plays a major role in the war for the United States East Coast, using its fellow Sabbat as Cannon Fodder or torture victims when it's bored. One luckless failed assassin is reshaped as its servant, tortured and broken so it may experiment with how loyal it has made him. With a thousand year reign of horror, an insatiable hunger for knowledge and an unspeakable appetite for torture, Vykos is the one who shows the rest of the Sabbat what it truly means to be a monster.
Quite a bit of the Ravnos clanbook was snarking at the others. Comes of being a clan of jokers to start with and then having little left to lose after the Week of Nightmares.
There's a Mental Flaw, "Stereotype", that makes you act as a camp vampire (accent, cape, the works). Stereotype returned in V20, but in addition to the typical Bela Lugosi homage, this flaw can now also cause you to want to cover your skin in body glitter.
Evil is Cool: Supposed to be subverted. However, some writers play it straight, usually with some of the most atrocious Clans.
The Russian part of the fandom tends to refer to Old Clan Tzimisce as "Zimischi". The clan's original name is just as unpronounceable in Russian as it is in English, and the Old Clan faction is canonically prominent in Russia - so it needs a Russified name, and Zimischi it is. It means something like "Great Winters". Most use a different transliteration for the Sabbat Tzimisce ("Tsimiskhi" is the most common). So there is Tsimiskhi the Sabbat clan, and Zimischi the Independent clan.
Memetic Badass: Smiling Jack, even in the pen-and-paper game. A Brujah ex-Pirate who has no problems getting with the times.
The prose introduction for the Baali clanbook features a supposedly respected abbot having sex with a preteen boy. After a few minutes, misshapen maggots begin crawling from inside the boy straight up the man's urethra as the boy, a Baali vampire posing as a mortal, clenches down with his knees to prevent the man from escaping, breaking several ribs in the process as the maggots begin burrowing, feeding, and laying eggs in his abdomen. This is only part of how the Baali choose their new initiates. At this point, you can stop reading now and count yourself lucky.
The original Clanbook Tzimisce. The illustrations look like what might happen if H. R. Giger and Salvador Dalí had been fused into one person. Which, come to think of it, is something at least one Tzimisce probably thought about doing.
The same person also illustrated the entirety of the original handbook for Wraith: The Oblivion. Enjoy!
Out of Focus: If you read the first or second edition rulebook, you'll get the idea that the game is a power struggle between the Brujah, anarchs, and young vampires in one camp and the Tremere, Toreador, Ventrue and elders in the other. Everything encourages player characters to be heavily invested in the conflict. As the Metaplot progressed, the Tzimisce, Setites, and the Salubri gradually took over the narrative; out of the initial big four only the Tremere retained their relevance right to the end (and mostly because of their connection with the Salubri founder, Saulot).
True Art Is Angsty: In many ways Vampire: the Masquerade (along with Warhammer) created the Darker and Edgiermovementof today and the original Gothic Horror of the 90's. The nihilism of Generation X, depression, punk literature and bleak mindset of the turning of the Millennium is what gave force and shape to this setting. It was so dark and bleak at its peak that Castle Falkenstein and many other tabletop games were created specifically as an escape for roleplayers who didn't want a dark, soulless, brutal game everytime they touched a die.
The Woobie: Clan Salubri's backstory is so tragic you want to hug them.
From the adventure Lair of the Hidden, there's the Cappadocian Drenis. She was born a male in the second century AD, but after being gang-raped by enemy soldiers and being unable to consummate his arranged marriage due to the resulting psychological trauma, he ran away and joined the priestesses of Cybele, having himself castrated and becoming a woman in every other way as well due to 1) being disgusted with the male gender entirely after his experiences and 2) believing he would be "in a half-state, neither a man nor woman" until he went through with it. The descriptions of the character elsewhere in the book makes it clear that the psychological scars have persisted over the centuries, even suggesting that Drenis entered into the pact with the demon out of self-destructiveness ("There are deep wounds in Drenis' psyche, a fundamentally gentle nature long subjected to horrors beyond its capacity, and so she sometimes behaves in ways no one, including she herself, can really explain"). Add to that the fact that she's one of the few good members of The Twelve (she's Humanity 7, the human baseline and second only to the senile-but-gentle mad-vampire Demetrius), and you really feel bad for her.