Great watch, will watch again, and can recommend.
I'm extremely biased as I've watched this repeatedly: I really like modern, palatable adaptations of Shakespeare (which we seemed to quit after this), this even got me over not liking Kirsten Dunst.
I get it if you think this movie is dated, hell it has Vitamin C and Sisqo in it, and it is full of tropey stuff, but when this was made, that was relatively newer stuff, and some of the things that people make fun of in later rom coms stems from this movie and its late 1990's early 2000's family.
Music / singing in movies is fun, it's not always great, but it's usually fun (see Trolls: most people have fun, it doesn't "help" the story though), and setting a complex teen rom com at a high school level makes the music an easy palatable distraction.
And this movie has a great cast, they clearly had fun making it: Martin Short of all people, even in 2001, Mila Kunis, Ben Foster, Colin Hanks, Zoe Saldana, Shane West, and even Carmen Electra makes an (uneccessary) cameo.
While I'll admit the story is a little rudimentary, extended from Mid Summer Night's dream, and relying on stock characters to basically do what stock characters stereotypically do, there is just a lot of charm in this. For me, it's about demonstrating the relationships between the characters to make the world feel real.
