I know it's a musical with a lot of modern sensibilities imposed on the characters, so I'm more asking about where it's wrong about actual events and relationships. I'm very curious to hear how it stands as basically a super popular Schoolhouse Rock.
Hey. I actually answered this the other day. Which can be found here: https://www.reddit.com/r/AskHistorians/comments/416pzc/how_accurate_is_the_musical_hamilton/ But here it is again for you:
http://earlyamericanists.com/2015/08/07/hamilton_review-2/ http://earlyamericanists.com/2015/02/25/bastard-out-of-nevis-lin-manuel-mirandas-hamilton/ These two blog posts should answer your question. The junto is a blog by historians of early America so naturally they were very excited by the release of such a popular musical on their topic of expertise.
The musical gets most things accurate, Lin Manuel Miranda has said that the musical is based on Ron Chernow's biography of Hamilton, this is probably a good book to start with if you want a full biography of Hamilton. But there are a few minor inaccuracies. For example;
In response to the election of 1800 Madison sings "you won in a land slide," in reality this was a quite a close election
Furthermore Hamilton was not fired by Adams during his administration, as it is depicted in the show.
Washington's farewell adress does not come immediately after Jefferson's resignation. It happened years later.
But this should not detract from how well the show does other things. The capturing of the cabinet splits in rap battle form is magnificent and Daveed Diggs' Jefferson is excellent. I hope this answers your questions on the topic.
Here's one interesting one. The timeline in the second half of act II goes as such:
Philip's duel
The Election of 1800
Alexander's duel
Historically, it actually played out this way:
The Election of 1800
Philip's duel
Alexander's duel
It was rearranged this way to avoid the crushing depression that would set in if the last two big events in the show were father and son both being needlessly slain long before their times.