1. Jules Winnfield - Pulp Fiction
Miramax Films It was inevitable. Every list like this that features Vincent Vega has to feature his counterpart, Jules Winnfield. Jules is the heart and soul of Pulp Fiction, and not just because he is played with fiery commitment by Samuel L. Jackson, but because he has one of the strongest character arcs in a film full of strong characters. Jules is the quintessential honest hitman - starting the film acting like a stone cold killer, and ending the film with a new sense of purpose. Jules is easily the single most quotable henchman of all time, despite only appearing in three segments in Pulp Fiction. While he shines bantering with his partner, it is in their "professional" scenes in which he steps into the limelight. His performance is almost a definitive statement on what it is to be a movie hitman - chat for a few minutes while walking to the job, "getting into character", and then pulling out all the stops and scaring the sh*t out of your victim. Jules gains most of the sympathy from the audience toward the end of his storyline - since he is not as hapless as Vincent, he is often relegated to playing the straight man of their double act. However, when they experience the mysterious "act of god" following their conflict with Brett and friends, he pulls back from his initial behavior and becomes more introspective, to the point where he can analyse his own favourite bible verse, using it to come to terms with his own identity as a hitman. Now that is quite a lot to think about while mitigating a Mexican standoff.
If there are any exceptionally sympathetic mobster minions you think we left out, feel free to mention them in the comments below!