It may not be appropriate to compare West Side Story (1957 broadway success and 1961 film) with A Cinderella Story (2004), but by interpreting an old story through a contemporary lens ultimately both projects did the exact same thing. The former just happened to do it 50 years earlier which provided for a setting that makes it feel classic today. I don't know as much Shakespeare as I should, but I like Romeo and Juliet a fair amount and that's probably why I think the focus and the tragedy of the story is somewhat lost in West Side Story. The exposition is great with the urban setting, and I love the first 20 minutes of the film version with the fun snapping scene at the basketball court and the early Sharks/Jets confrontation. It's easy to see with its cinematography why the 1961 film is ranked by AFI where it's been hovering around the top 50. Everything tonally in this opening sequence is communicated without words which is an impressive accomplishment. Similar to The Outsiders (1983), however, it's a slow downhill from the start as the strongest visuals fade away and the plot's ultimate payoff is disappointingly underwhelming.
I can't speak for any of the original or professional productions of the show as I've only seen school productions, but musically everything in the film adaptation seems to be quite well done, particularly in terms of choreography as some numbers are actual dances while others are fight scenes among the rival gangs. This mix is interesting and preserves the elements of art which could have been replaced with poorly-executed action considering the time period of the movie. I acknowledge the songs and dance numbers as spectacular, but that opinion is more appreciation than reverence because personally I don't enjoy all of them. Some of the Puerto Rican women stuff is too much for me to take like when I have to leave the room for a minute or two during a Disney movie if I find one of the songs too annoying.
West Side Story is good, but when it comes down to it I'd rather watch a version of Romeo and Juliet (any version, I'm not picky here) for the full scale of the romance and tragedy or Grease (1978) for the teenage antics and more entertaining and lively musical aspect. At least for me, West Side Story manages to fall short in each regard by trying to achieve both the fun and the drama. I think the 1961 film is an iconic and clearly definitive version of the production, much like the 1965 adaptation of The Sound of Music with Julie Andrews, but for me it's still a bit overrated. I acknowledge and recognize West Side Story as one of the prolific contemporary musicals, but it's just not one of my favorites.