Beyond the surface-level pithiness of the joke, the point is that having money may not guarantee happiness, but it makes it a lot easier to distract oneself with viscerally pleasant experiences and engage in new hobbies that may in fact lead to genuine happiness.

I appreciate that it says you never SEE an unhappy person riding a jet ski.

Whether or not it generates happiness, money can make happiness more visible. That's worth a moment of reflection.

Hmmm. Bourdain, Robin Williams. I don’t think you can distract yourself from depression.

Robin Williams actually had a degenerative brain disease. I know a lot of the news didn't wait long enough for that information about his situation to come out, but it's on Wikipedia.

That's missing the point of the saying.

They did a study once that indicated the first 95k buys happiness, but money after that, not so much.