Dang, there sure are a lot of hitman characters in the movies. And what's the difference between a hitman and an assassin, anyway? Does Jason Bourne count, or is he no longer a hitman/assassin by the time his cinematic story begins? Are Pulp Fiction's Vincent and Jules really hitmen or are they technically bagmen? Yeah, it's a difficult task to make a list of prominent hitmen in film. So, I'll let someone else make a "25 Greatest Hitmen" list; here, I present my seven favorites.
Feel free to mention your own preferences. With so many characters, whether easily falling within definition or not, I'm certainly leaving out a lot of good ones. But, as I said, these are my favorites. The cool, the funny, the interesting, they're the ones I enjoy watching over and over again, despite their lethal nature.
Martin Q. Blank in Grosse Pointe Blank (1997, George Armitage)
There is no better hitman than John Cusack's Martin Blank. He's good at his job, and he's funny, and he's willing to give it all up for love. Of course, he's bored enough by the occupation that he'd probably give it up for any good reason. It doesn't seem to matter to him that it's morally wrong; he's just another normal guy, dissatisfied with his job. And while it does seem to be a gag that's stretched thin, his issues do make him more entertaining than the usual silent-yet-conflicted hitmen. Plus, it's enjoyable to think that this is what really happened to Lloyd Dobbler, or Lane Meyer, or any other Cusack character from the '80s.
Signature line: "I was hired to kill you, but I'm not going to do it. It's either because I'm in love with your daughter or because I have a new found respect for life."