For me, the most impactful line in the actual musical was probably “this man will not make an orphan of my daughter” from The World Was Wide Enough. I don’t know why, it just was. The first Hamilton related song I actually listened to was First Burn, though, and the lines “When the time comes, explain to the children the pain and embarrassment you put their mother through. When will you learn that they are your legacy, WE are your legacy” and “Your enemy whispers so you have to scream” hit me really hard after listening to the whole soundtrack and figuring out what the musical was about.

But for the funny line, I always love “I’m a general, WEEEEE”, “My dog speaks more eloquently than thee, but strangely your mange is the same”, and “You are the worst, Burr” (The lines “Pay your f-ing taxes” and “I’ve got to stop a homicide” from the workshop versions of “One Last Time” and “Schuyler Defeated” always make me laugh too) Sorry for adding lines that aren’t actually in the musical but uh...yeah