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(Audio of the) Mandatory meeting after Madison's departure from LMG.
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This is some high school humor and if you watch any of the videos where James and/or Riley get to play off of each other, it gets really cringe really fast. It probably seemed innocuous enough when they were smaller but it sounds like James is too comfortable with his buddy Linus and has the same lack of awareness to take things seriously.
Yeah, I would have to agree, it's the kind of thing that's perfectly okay amongst close friends, but not in the broader public/workplace. The reality of growing to a company of their size is that they have to mature up as well. They probably should have had the new CEO a long time ago.