Content warning: Some is not work friendly. There’s some bad language, though most of it is beeped out, so if that’s not your cup of tea, buyer beware.
I find Key & Peele consistently funny. They do this thing really well where they simulate a dramatic situation and then come up with what people would actually do in that situation. For example, at a slave auction:
Normally a tense, tragic situation for the slaves, fellow slaves go from bragging about the revolution they’ll start on their new plantation to dismay about not being bid on, to desperate job interview-type pleadings (“Have I mentioned this? Docile. I am agreeable to a fault. You should have seen the dude that asked me to get on the boat. Just walked right on, no big deal, never seen a boat in my life.”).
It combines bro-bragging with objectifying with male competitiveness with racial tension.
Here’s another one, a vampire coven/cove/cluster thingy.
In both cases it starts out with identifying with existing media, then parodies it by bringing in characters who call the tropes out. What if you were only a vampire because you wanted to be alive to see flying cars?
A recent one, where I literally laughed out loud:
Not only are they making fun of the types of music videos that can get made (with some restraint, I think) but they tie it to how expensive certain parts or props are. The shift half-way through is where I started laughing aloud.