Things can be both funny and disappointing. He found disappointing things to say and made them funny with observation; it was his schtick, his only schtick. He was 'edgy' before edgy was hot. Low-effort humor, still funny to an extent, but a lot of people used it as a bar for their own disappointing observations, it bred acceptance of hate and racism because they thought funny == good.

Some people cannot separate their comedy/actions from what they should and should not do in real life. It enabled the "settle down it's just a joke BS". They idolized him; he became wealthy and a conservative mouthpiece.