I'm sure Stephen Sondheim and James Lapine's classic 1986 musical Into the Woods wasn't my first twisted fairy tale (that might have been something by Jon Scieszka) but it's the one that made the strongest impression, and it continues to impress me today. The music is complex but catchy. The lyrics are clever. Add a showstopping witch as a villain/plot catalyst/antihero and it's no wonder the thing has seen multiple Tony awards and successful revivals worldwide.
As a fairy-tale retelling, I believe Into the Woods succeeds because it does the three things all retellings should: it understands the source material, it remakes it in an insightful way, and it adds its own value.
Respect the Source
The first line of Into the Woods is "Once upon a time." Its last line is " -- and happily ever after!" (Plus a tiny, tiny coda that sums up the musical's themes. More on that later.) Most of the characters are named for their roles: the Witch, Granny, the Baker's Wife. The first act spins together five separate tales -- one of them invented, but so pitch-perfect that it makes you wonder if you've simply never read it before -- and though they're performed with winks and wry smiles, they're played perfectly straight. The only twist is their combination, which is a pretty clever one, though increasingly common. The first act shows two things: that Sondheim got his inspiration from sources more reliable than Disney movies, and that he understands that the stories are sufficient, without change, to hold an audience's attention.
Then the second act happens.
Tear It Down
Spoilers! It's entirely possible to watch the first act of Into the Woods and quit happy. Sure, there's a called-out "To be continued!" but that act, like the second, ends with " -- happily ever after!" It's a good stopping point for little kids or, perhaps, adults uninterested in shattering a pleasant illusion.