Craziest thing? Well so... far. It was coming across the Habeeb Taxi Union, not really knowing what to expect. But my character's goals were to get a good job at the time, so he would've taken pretty much anything as long as it was legal.
I was guided by a IC friend to the place, and I expected something really cool and fancy... Instead I see what looks to be a former gas station turned into a Taxi vehicle depot, with the lights on the outside entrance blinking. Add that by the desert ambience and the nightly desert atmosphere... I bursted out of laughter oocly, thinking what I had gotten myself into... I get beckoned inside the building with a "Is he facka blind?..." and I remember I am supposed to be taking an interview... I thought it was going to be some basic interview, but boy I was wrong. First thing he asked was my name, I gladly gave him mine. And he returned a reply, "Ah, yes. Sammy Woodcock." And I kept laughing throughout the whole interview as it was really just some out of the blue questions. I did some training, but it was abruptly stopped by a serious drunk hit-and-run on my IC friend and had some more great laughs and great roleplay the more I spent time with them the next following days.
Now after interacting with the characters and just generally hanging out with them... That place and Habeeb employee's/friends will always remain a good reminder to myself what good roleplay looks like and how fun and great GTA World can be <: