6. Vincent Vega - Pulp Fiction
MiramaxIn many ways, Vincent Vega is the most iconic sympathetic hitman - despite working for a ruthless gangster in Los Angeles, he is a laconic & philosophical dude who hangs on long conversations about foot massages and overpriced milkshakes in between the brutal spots of violence that characterise his career choice. Considering he is the brother of the sociopathic Vic Vega (Mr. Blonde from Reservoir Dogs), Vincent seems like a genuinely decent guy. He gossips about his boss, gets into ethical disputes in the workplace, and gripes to his local drug dealer about some jerk vandalising his motorcycle. By this description, you wouldn't even guess that his job happens to involve killing people for money. But when that bit comes up, Tarantino knows a foolproof way to keep Vincent from becoming dislikable. Tarantino's ace in the hole with this character is his crushing haplessness. The most ironic moments in Pulp Fiction come from the frequent times when things go horribly, horribly wrong for Vincent, and he has to work madly to get himself out of the jam that he got himself (and his partner) stuck in. He is phenomenally unlucky, and that bad luck translates into extreme sympathy for the audience. It is fitting that he died because he didn't bring his gun to the toilet with him - doesn't mean it doesn't make us upset.