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. Changing his gender and taking the name "Sascha," Vykos became a major figure in the monstrous Sabbat, feared even by her monstrous Clan. Vykos invents new tortures, having perfected them upon countless unwilling victims whose agony she can prolong for years to centuries, alternating it with incredible pleasure to make the victim unsure if it is experiencing torture or rape. In modern times, Vykos plays a major role in the war for the United States East Coast, using her fellow Sabbat as Cannon Fodder or torture victims when she's bored. One luckless failed assassin is reshaped to her servant, tortured and broken so she may experiment with how loyal she 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.
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!
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 Millenium 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 dice.
This is averted in Ari Marmell's Gehenna: the Final Night novel, where Beckett meets a vampire calling himself Kumpanios who is a helpful, curious, friendly, vampire and is actually Caine, despite not actually admitting it.
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.