I can’t claim to know everything about retellings. All I know is that retellings have been a part of literature since before William Shakespeare leaned from his desk to take a peak at Christopher Marlowe’s paper during their fifth grade spelling test.
At the moment, I am working on a retelling of Rapunzel. It’s set in a modern time, but with some fantastical elements included that hopefully make up for the leaps in logic the story inevitably takes. No one was complaining when Rapunzel first appeared, that their hair couldn’t possibly support that weight. So I feel confident that the direction I take with my version will be well received by some, if not by all.
Neil Gaiman (wow, I bet you never thought I’d reference him in any one of my blog posts) wrote a retelling of Homer’s Odyssey when he wrote American Gods. Similarly, a novella also involving the hero of Shadow Moon, included in one of his collections, was a retelling of Beowulf.
Sometimes two stories can have a similar premise, without being retellings. If I ask you to tell me the title of the story about the eternally youthful boy who sneaks into a teenage girl’s bedroom and tempts her with immortality, you might immediately think of Twilight. But that’s also the basic plot of Peter Pan. Twilight is not a retelling of Peter Pan, anymore than The Hunger Games is a retelling (or a rip off) of Battle Royal. They’re different stories that explore similar themes, and are more indicative of the common lines of thinking that people can sometimes unknowingly share.
If I were to offer one simple guideline when writing your own retelling, it would be this; the bare bones of the story has to be familiar to readers. It’s okay if they don’t get it at first. But if you tell them that The Lion King is a retelling of Hamlet, then their reaction should be, “Oh, now I see it.”
Hopefully, when people read my story, it won’t be necessary to point out the connection to Rapunzel. There are people who will miss it. There are also people who see a blue sky and insist that it must be red. You can’t win them all, as long as you try your hardest to win some.