9. Rocco - The Boondock Saints
Indican PicturesTroy Duffy's 1999 cult film The Boondock Saints has a remarkably divisive reputation - some love it as an over-the-top black comedy, some vehemently despise it as a cheap Tarantino knock-off. But one area in which most people will agree is that it is filled with memorable characters. One of these characters comes in the form of Rocco, a hapless low level mafioso in Boston, Massachusetts. Rocco is a hilariously pitiful character. A friend of the titular Boondock Saints (brothers Connor and Murphy MacManus), Rocco is desperate for advancement in the local drug cartel, but he is treated with absolute contempt by his fellow gangsters, who give him the patronising nickname "The Funny Man" for his awkwardly racist jokes. Rocco, after being betrayed and sent into a death trap, finally snaps and joins the MacManus brothers on their holy crusade against crime - although he is not nearly as successful at it. If The Boondock Saints were a band, Rocco is the Ringo - despite having critical connections, he is completely incompetent compared to everyone else in the film. He is an idiot, but his frustration at the world of organised crime comes from a real place - feeling rejected by their world, he decides to try his hand at being vigilante. He is always caught between smarter and more competent foes, which in some ways makes him the most human character in the film.