My personal favorite for flawed reasons is Madoka because I was there for the live reactions to the infamous episode and it was magical watching everyone lose their shit. It was also my re-introduction to anime after being shamed out of it for liking sailor moon as a kid.
Tim Heidecker comedy special, where his whole hour bit is just him being a compilation of hack mysoginist comedians
Him doing the Joe Rogan knockoff with the Fuddruckers sign was :chefs-kiss: