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Some characters get all of the coolest lines. James Bond gets to introduce himself by last name first, Darth Vader gets to (spoiler alert) proclaim that he is in fact Luke Skywalker’s father, and even Don Vito Corleone gets to explain how he will make someone an offer they won’t be able to refuse. These are lines that can only be uttered by those particular characters.

On the flip side, there are other lines: lines that just ooze badass, but basically anybody can say them. One of those lines is, "I should have killed you when I had the chance." Check out the compilation video below to see just how many times that particular phrase has been spoken in movies over the years.
Across myriad genres and an insane amount of movies, the supercut showcases iconic film characters – hero and villain alike – claiming that they should have killed someone when they had the chance. It’s the sort of line that sounds great in a sweeping, epic movie, but compiled together one also realizes how much movies have long relied on familiar tropes to get certain points across. Sometimes it’s employed for comedic effect, while at other times it’s used to sell a major dramatic moment; either way it’s a trope we have all come to know and love.

You probably never realized how much that particular phrase, or at least some variation of it, gets uttered at the movies. However, hearing them all at once makes it clear just how many films have employed that particular convention. The video also draws attention to the heightened drama that exists in the world of film. Be honest, you don’t actually think people talk like this in the real world, do you? 

It can also be said that the same phrasing has been used for a significantly more pleasurable experience. Rob Schneider's less than successful comedy The Hot Chick saw him uttering the phrase "I should have made love to you when I had the chance" to Matthew Lawrence.

Despite how awesome all of these variations of the same phrase are, it all reeks of melodrama and, at times, lazy screenwriting. In some cases it absolutely works – I have a particular fondness for Ian McKellan’s Magneto screaming the phrase – while other times the delivery of the line can fall a bit flat.
If you haven’t checked the above video out for yourself yet, be sure to do so. It highlights the sort of conventions every film buff has seen a million times in theaters, but seldom thinks about. As long as there is violence in movies, there will always be people ruing the fact that they didn’t kill someone, get killed, or get killed by someone, when the perfect opportunity had presented itself.