Call of Cthulhu characters, both by the same guy, for a Masks of Nyarlethotep game. The rest of the group included a Starlett with an interest in the occult, a wealthly playboy who fancied himself an adventurer, and a professor of archaeology at Indiana Jones University. (No, it's not really where he taught. You get the point, right?)
Firstly, after hearing that it really was an investigative-heavy game where fighting would not be a frequent occurrence, he created a gun toting russian/irish mobster with nothing but combat skills. He spoke very little english, was barely literate, and for some reason had a number of "chivalrous" character traits tacked on for interest I suppose. He was the star of several sub-plots, including the "Mystery of Why the Fuck did you Dynamite that Apartment Building?" and "The Case of Why Did you Shoot A Bunch of British Houses With a Thompson?". His final moment was in the middle of thousands of evil cultists when he decided to toss a stick of burning dynamite onto the main stage. He was in disguise, but I pointed out that throwing something while surrounded would instantly give him away, no matter how ridiculous his stealth roll was. He did it anyways.
Then, to fix things, he created a navy seaman who was for some reason being held captive in cairo by the cultists. Since he was an officer, he decided his skills should be focused on leadership and ordering people around, but that he "gives orders, he doesn't actually do stuff. So he won't have any kinds of useful skills, just Leadership and Inspiration and such." He walked immediately into the group and said, pretty much verbatim, "I'm a great leader, so you need to listen to me." They tolerate him because of his player halo, but his (again) complete lack of any investigative skills has made him very few friends, and "I try to inspire X with my inspiration skill" (where X is some sort of inanimate object or inappropriate situation) has become a running joke in game. Because you have to laugh to keep from crying.
