He's presenting this to his company. I don't think this video was originally intended for mass consumption, but I am glad it was made available.
So this is the CEO presenting to a group of people who know him and his presentation style, I think at that point much of the stuff you're complaining about can be thought of as humor or house style, especially when you consider that Joel worked at Microsoft on Excel. Context matters.
As someone who watched the live stream of the original presentation from the Stack Overflow lunchroom I can confirm that the video is missing some context. Definitely a bit of house style and a throw back to some old school memes, but overall an informative and humorous training session that I am glad was made public.
Joel usually gives great presentations, and recently he even started personally editing our internal company update videos (and complaining when we don't show appreciation by up voting them :-) because the first one was a bit dry.
So this is the CEO presenting to a group of people who know him and his presentation style, I think at that point much of the stuff you're complaining about can be thought of as humor or house style, especially when you consider that Joel worked at Microsoft on Excel. Context matters.