What is an obscure piece of media or videogame that you think nobody else here has heard of?

There was a door (plugin) for The text-based *BBS game Legend of the Red Dragon called Violet's Tavern.

You could sit at the bar and buy a drink that enhanced your stats, You could go upstairs and pay for a hooker to replenish your energy or you could try to seduce the barmaid / owner and actually have kind of a sweet encounter with her.

It had a betting mechanic I don't remember if it was blackjack, dice or what but you could game it a little bit by throwing a shit ton of money at it a few times. The initial odds to win or somewhat higher than the extended odds to win so if you hit it and hit big you just walk away. Sometimes you ended up empty but more often than not it worked.