The qualifiers make this harder to answer than expected. Given the many vampire games my group has played through the years, choosing the craziest thing is a tricky prospect. We've had neonate games, anarch sessions, Sabbat romps, elder campaigns, cross-generational stories and even multiple arcs of the same story (Giovanni Chronicles was run four/five times, depending on who you ask. Transylvania was run around thrice. The Gehenna book has been used a few times too, in once case having ALL FOUR SCENARIOS merged into one.)
There was even that one game where the players were portraying the Antedeluvians when they were still neonates and the game was set in the ancient times. Oh yes, they would worry each time I'd mention in a scene that it was raining pretty hard. Good times. I should run that game again.
But I guess the craziest game we played would be our multi-character spanning session which I ran very many years back. I forget what I called it, but the game basically was approached in this manner:
1) All players are Kindred Special Agents
Yes, you were a vampire. And you worked for a special ultra secret branch of the government.
You were tasked to deal with threats and handle the maintenance of National Security.
2) Powers were gathered into a Pool of Assets
Every single power in Vampire the Masquerade, Vampire the Dark Ages, Werewolf the Apocalypse and Wraith the Oblivion were gathered into a single pool. During Mission Briefing, players would select up to five powers which they planned to use. So yes, you can, for example, have: Step Sideways, Telepathic Communication, Celerity, Form of Mist and Theft of Vitae while your fellow agent might be armed with Body of Sun, Fortitude, Sense Wyrm, Movement of the Mind and Mask of 1000 Faces.
Powers worked normally, but those that were beyond your Generational limits would cost an additional health level and willpower point to use. Any powers that were non-Cainite immediately were considered beyond Generational limits. And lastly, all uses of powers beyond level 5 cost three extra blood points to use each time. So the Agent with Body of Sun? Each turn he activated it, he would need to spend 1 Health Level, 1 Willpower point, and 3 Bloodpoints to activate (standard system) plus 3 to use since it was beyond 5. Then required 2 blood points per turn to maintain (standard system).
This meant needing a Generation high enough to spend 6 in one go, or needing extra turns to "charge it up".
So it kind of balanced out :-)
3) The Enemies were the Ancients
The game progressed with the players learning the names of the counter-intelligence forces were Arikel, Malkav and the like. This, of course, freaked them out big time!
4) Finally, the game ended with one single player being told the truth.
The rest of the players had an awesome romp fighting international threats and forces. And the game ended with them just happy the world was saved.
One player was allowed to break free from the illusions and telepathic manipulations the rest of them were in. The Ravnos elder whispered to him that is what happens to those who cross the Ravnos. Then he silently committed the Amaranth and took that character's soul away. The rest he was to devour at his own leisure.
That player never told the other player to this day.
(Or at least that's what I believe since none of the others ever told me about this game's secret ending).
Now, if the entry were to require craziest thing a player did, rather than what a GM did, that would be a True Brujah player using Temporis to halt an ongoing battle between fellow Cainites and a pack of Sabbat hunters, then the same said Brujah raising his glock to shoot the Sabbat Pack Leader, but botching his roll so bad, we ruled he just shot his ally in the head.
Definitely a WTF moment we all enjoyed.
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