I don't see that. That other story is from a special that was recorded a year prior. This joke came right after he said that transgender people have a "tough road ahead" and that they're gangsters. The joke is basically how ridiculous it would be if someone who wasn't transgender just decided to change their gender frivolously like it was a dare.
Now, the story about the person ODing at the gallery show does come off more ignorant, but I do think it's just him being ignorant about that shit.
Bro you don't have to explain the joke to me. It's not that you "get it" and I don't. I just found the rhetoric to be kind of gross and very tone deaf.
His joke about being scared/grossed out by the transgender woman in the meeting was also offputting. Whenever he brought any of that shit up i coulnt wait for him to move on.