I will be honest with you here, and let you know that I barely remember this play.
There were only a handful of Shakespeare’s plays that I made it out of school not having read, and this was one of them. I’ve been meaning to read it for years but never seemed to get around to it. Honestly, I wish I hadn’t read it, because at least there was a pleasing sense of mystery to it, with me wondering what it was about and only imagining good things. I had no idea it’s considered to be one of his “problem plays” (a term which doesn’t mean what you think it means, but works well in its original context but also if you use it to just mean “problematic”, because it certainly is).
The “problem” for Shakespeare scholars is that this play isn’t a true comedy, nor is it a tragedy or a history, but has elements that sort of slither back and forth. It’s not easily categorizable. As someone who absolutely loves genrebusters (and a mix of tones) I see no problem with this. My problem is with the story, which is about the Duke of Vienna, who decides to be tricksy and deputizes this dude Angelo (I had to look up these names while writing this) but then sneaks back into the city in disguise to watch how the city fares without him as basically an ego trip.
Angelo stirs up some shit. He closes all the brothels. He tries to hang people for sexing outside of wedlock. Then asks to take a woman’s virginity in exchange for him not hanging her brother. This is so funny so far. Anyways, everyone ends up getting their due, but the whole thing feels very unnecessary because you feel like the Duke knew Angelo was a shithead, and instead of just shitcanning him or exiling him or whatever, he wants to like, humiliate him publicly first. Then he gets rewarded with the marriage of a virtuous woman and this other dude Lucio (who humorously had been slandering the Duke to his face while he was in disguise) is made to marry a prostitute he seduced and abandoned, who is now having a baby. So, things end up good for the good guys and bad for the bad guys, in true Shakespearean comedy fashion, but there’s just this icky sense you have the whole time, like this just doesn’t feel good, guys.
I think you could probably make a case that Shakespeare’s social commentary here about sexual hypocrisy and the mores of the time were pretty incisive, but it’s also just sort of a mess. I’d skip this unless you’re a completionist.