James Mickens, 'The Saddest Moment' - https://scholar.harvard.edu/files/mickens/files/thesaddestmo...
edit - further wisdom;
James Mickens, Associate Professor, Authority On All Things, Harvard - https://mickens.seas.harvard.edu/wisdom-james-mickens
Wtf? Reeves is a rather kind man who had some horrific life tragedies and yet managed a successful career (with no scandal). Why would I be sad about that?
"I always feel an immediate, unshakable sense of sadness" - presents a personal and serious context - "kind of like when you realize that bad things can happen to good people," - reinforces the seriousness and invites the reader to join the writer in worthy feelings of moral empathy - "or that Keanu Reeves will almost certainly make more money than you over arbitrary time scales." - then punctures it with base motive of bitter jealousy, so you get conflicted by the two very different versions of sadness being presented as the same thing.
Structurally, it is not far off Shakespeare's lawyer joke from King Henry VI;
JACK - when I am king,– as king I will be,–
ALL - God save your majesty!
JACK - I thank you, good people:– there shall be no money; all shall eat and drink on my score; and I will apparel them all in one livery, that they may agree like brothers, and worship me their lord.
DICK. - The first thing we do, let's kill all the lawyers.
This explanation however, has probably stopped it from being funny ever again, for which I humbly apologise.