There was a stretch in Fall 2016 when I listened to the soundtrack for Hamilton constantly. I spent a lot of evenings going on runs because my wife and sons had not moved to Nashville yet. I found out that the first act of the musical roughly coincided with the time that it took me to run eight to ten miles (man, I miss the guy who could do that). Songs like “My Shot” and “Yorktown” gave me a shot of adrenaline to pick up the pace while the songs like “Helpless” and “Wait For It” let me settle into a more comfortable groove.
As such, I like the first act of Hamilton way more than the second. Granted some of that has to do with the fact that Act I is this ragtag group winning the Revolutionary War while Act II is Hamilton letting his ego and libido lead him to do dumb things and multiple characters being murdered because of antiquated ideas about honor. Plus there are not as many bangers in the back half (though “Room Where It Happened” and “What Did I Miss?” are fun; it’s a good musical!).
All of this is a long preamble to say that the most cringe moment, to borrow a phrase I generally don’t like from Gen Z, is at the end of “It’s Quiet Uptown.” The song finds Alexander Hamilton wandering the streets as his professional and personal life has come unraveled. Spoiler alerts from American history upcoming: a sex scandal has ruined his reputation and his son was killed in duel trying to defend Ham’s honor.