Aligning characters ambiguously (remember The Princess Bride?)

I'm a sucker for ambiguously aligned characters. Good guys who turn into bad guys, bad guys who turn out to be good guys, those folks are just plain fun. I write stories with this kind of character all the time, but I was reminded of them recently when my kids and I watched The Princess Bride.

I'm sure most of you are dearly familiar with Inigo and Fezzik. During our first viewing I became fascinated by the fact that these two characters are immediately likeable despite the fact that they've just kidnapped the princess along with Vizzini. So during our second and third viewings (since people, especially children, like to see fabulous things more than once) I took a look at our introduction to these two characters.

Basically, after our first view of them which involves them knocking out Buttercup, we immediately shift, not to her point of view of them on the ship, but to their own internal squabbles. Inigo demonstrates curiosity about what exactly they are doing ("what is that you are ripping?"), showing that he's not entirely aware of their mission. Then when Vizzini describes the basics of of his plan to frame Guilder by killing Buttercup and leaving her on the frontier, Fezzik reveals that he wasn't totally in on the plan either, and that he has morals well-aligned with our own ("I just don't think it's right, killing an innocent girl."). We then get an opportunity to witness Vizzini's cruelty applied to his own accomplices as he dresses them down.

This is a good start, but on its own, I don't think it would be enough to convince me that Inigo and Fezzik were anything more than weak bad guys, or at a stretch, decent guys forced into nefarious deeds by circumstance. The point where I really start liking them is when I see Fezzik clearly have hurt feelings as a result of Vizzini's tirade, and then Inigo comes over to him and starts deliberately consoling him by starting the rhyming game. At this point, these two characters are no longer simply henchmen who do their boss' bidding. They are actual people, friends in fact, who care about each other and also have a sense of humor... a sense of humor which they are entirely willing to use at Vizzini's expense ("Anybody want a peanut?"). This pattern is then confirmed as we go forward into Vizzini's mercilessness and Fezzik's inability to use his considerable power (the fact that he's literally dangling Vizzini over a cliff) to win an argument. It continues into Inigo and Fezzik's interactions with the Man in Black, where we are also given glimpses into the backstory of each character. In fact I don't think that it would be nearly as difficult to guess the identity of the Man in Black if we immediately concluded he had to be a "good guy" because Fezzik and Inigo were "bad guys."

I think there are some good lessons to be learned here about what it is that makes a character likeable. Readers and viewers collect evidence in a character's interactions which they use to establish that character's qualities and alignments. Clearly even criminal behavior (kidnapping) can be quickly outweighed by evidence of reluctance and human caring. It's good to remember this if you're creating ambiguously aligned characters, and even if you have a protagonist who has to do bad things. We don't blame Janice Hardy's Nya for stealing, because she's stealing eggs when she could potentially choose to steal something much worse, and then only because she's starving. Her human qualities come to the fore much more quickly.

What do your characters do to show us that they are human? Does it make them seem more complex? Does it make them likeable?

It's something to think about.