Into the Woods is a really smart twist of traditional fairy tales like Cinderella and Jack the Giant Killer. It retells several fairy tales in a single cohesive narrative - the quest of the Baker and his Wife to lift a curse on their family. Meanwhile, Cinderella, Jack, and a cadre of other classic fairy tale characters pursue their own aspirations in the manner traditionally depicted. Everyone has their wishes granted, but unintended consequences ensue.
Truth be told, this is my second experience with Stephen Sondheim: the first being the 2011 production of Company, which was a very pleasant surprise. Just like Company, the orchestration of Into the Woods is excellent. The play has a unique sound with a whimsical/fantastical quality befitting a musical about fairy tales. The lyrics are also impeccable - equal parts witty and catchy.
The book is also very clever. It touches on themes of consequences and parenthood that hit deep. Parallels are also drawn between characters that service the themes well. I feel that I should also emphasize that the play is very funny - mostly from banter between characters and several one-liners. Comedy pervades the dialogue and even the musical numbers. The writing of several characters is also worth noting. The Witch, especially, is not an archetypical villain. She is more here for her own good rather than a force committing evil for evil's sake. Her relationship with Rapunzel makes that especially clear.
Finally, the cast really sells the musical but Joanna Gleason and Bernadette Peters were the most memorable to me. Gleason (the Baker's Wife) and Peters (the Witch) both have great comedic sensibilities and then some that make their characters come alive. Gleason's Wife has a certain snark and street smarts to her that contrasts well with the Baker and others. Gleason meshes especially well with the Baker, being his North Star, lover, and co-conspirator. Peters, on the other hand, brings a jaded quality to the Witch that accentuates her character's morally ambiguous nature. She also adds a lot of whimsy to the character, in keeping with the atmosphere of the play.
Please, do yourself a favor and watch Into the Woods at least once. I would definitely rewatch this in the future because I am certain there is a lot more details that I missed!
