Is there a word that describes the act of smiling with a devilish grin? Or being happy for others misfortune? I always come back to the word "leering" but that's not it. For instance; (...) he leered at the prisoners around him.
I only know of smirk but that might be a bit lightweight for your needs. You might need an adjective like sinister.
leered implies lechery i think .. maybe sneered. or " A devilsh grin split his face, teeth gleaming in the flickering lamplight" or something like that
In the right context, grin works very well. Pulling the sword out of the scabbard, he grinned at the prisoners around him. "So who wants to go first?"
A wry smile. It's a subtle and condescending smile, as if part of the joke is at the other person's expense and they don't realise it yet.
You're not going to get a one-word answer with this one. Well, okay schadenfreude, for the noun, but for the smile you'll have to expand it. And it doesn't have to be "grinned evilly." It could be the way the smile appears: "a smile crept across his face" Or you could go for imagery: "he showed a smile with too many teeth" "his smile was like a skull's" Then you have a billion ways to do it.
He looked like a happy predator with upturned lips, waiting to deliver the killing strike. You know that creepy sinister kinda smile that makes a person look deranged, and you feel like they might feast on your flesh.
I'd like to offer a difference approach. Instead of focusing on the reaction (smile/smirk) focus on stimulus part of the equation, and with a little bit of internal dialogue. Example: "Screaming, The man struggled to break free as the fire devoured his body. Good, I thought and smiled." This will get the message across -I believe- a lot better than a word that some people might not recognize.
Leer and sneer more imply a disdainful glance; sneer works for a more condescending smile. I usually don't get the imagery of "smile" from "sneer." As others have said, two words, vice one, are probably a better way to convey the notion of an evil smile. Malicious grin, smug smile, predatory grin, etc. Exact verbage depends on what you want to convey. OJB's suggestion is probably best.
It might work better for the evilness to come elsewhere in the context--it doesn't necessarily have to come in the verb or adjective associated with the smile. That word could even be one traditionally associated with a positive smile. Janet turned back from the sink to see Victor standing behind Sally's high chair, a gun aimed at her curly blond head. Sally, contentedly oblivious, continued to gnaw on her waffle. Janet gulped and tried to speak, but no words came out. Victor beamed at Janet. "I think that we'll have that talk now, won't we?"
