Retellings of famous novels, fairytale retellings, and allegory all have the same challenges for authors: ensuring the story sticks closely enough to the original plot to satisfy readers without becoming predictable (or, worse, without having the characters act out of character in order to fit the prescribed plot elements).
The other challenge with retellings of famous novels is that readers are unlikely to read a retelling of a novel they didn’t enjoy.
Perhaps that’s why Jane Austen retellings are so popular: most romance readers enjoy Austen’s stories. The flip side is that makes many of Austen’s tropes overused, and it makes it harder for authors to find that unique twist.
I don’t read a lot of novels that are specifically signaled as retellings.
One I remember reading and enjoying was Dear Mr. Knightley by Katherine Reay, a retelling of Daddy Long Legs by Jean Webster, which I read and loved as a teen.
I think this book illustrated one secret to a good retelling: choose a story that has stood the test of time, but not one that is so well known that the author can’t find the original twist. I picked up the story was Daddy Long Legs early on, but read a number of reviews commenting on the “original” plot and the unexpected plot twist at the end, which suggests I was in the minority for knowing the story.
