IMO, Watterson stopped at just the right time to preserve his legacy and keep the strip associated with childlike wonder and innocence. In the last years of C&H there was a certain curmudgeonliness creeping in, as Waterson started to mock modern commerce and art. I think the cartoonist was naturally growing older and more disillusioned, and his strip faintly started to sound like Calvin’s dad instead of Calvin.
At least based on some of the things he's written in some of the anthologies, it seems like a lot of that disillusionment was not just because of age, but rather because of his battles with the publishers and what not that were pushing him to make changes that he felt would compromise the integrity of the strip. A lot of the comics include subtle jabs about corporate greed, artistic integrity, etc. because he was actively fighting with the corporations that distributed his strip over such matters...
Still, 100% agreed that he stopped at the right time, both because of the creeping cynicism, but also simply because he was running out of fresh ideas...
I'm currently working through the Complete Calvin and Hobbes with my 9 year old, and he had these jabs at commercialism throughout, though it might have been sharper towards the end, but he was already jaded by art in 1985 as a 27 year old.
He had dreamed of being a cartoonist from childhood (when he was 8 he wrote Charles Shulz of Peanuts who wrote him back and it changed his life). He had actually majored in Political Science at Kenyon College (class of '80) because he thought that political cartooning was going to be his route in. It was not. He was a political cartoonist at the Cincinnati Post briefly before they fired him, then he worked for an ad agency and freelanced a bit before Universal Press Syndicate signed him on for Calvin and Hobbes. But, even at 27 when he started working for UPS, he understood the pressure of the professional art world and was cynical about it.
Apparently he lived a miserable life for the last few years of his work. He had been injured in a bike accident and it terrified him that he would be injured in such a way that he could no longer draw (1) so he basically stopped going out, stopped doing anything that could possibly harm his ability to earn money, stopped doing anything that might bring joy to his life. He lived a recluse for several years, before deciding to just quit, then he and his wife Melissa adopted a child and gave her a good life.
1: Bill Mauldin, the Pulitzer Prize winning cartoonist who created Willie and Joe, was the editorial cartoonist for the Chicago Sun Times when, in 1991, he crushed his right hand attaching a snow-plow to his truck, and he had to retire. I think that incident is what inspired this fear, the timelines match up. But of course, Watterson is famously private and so this is conjecture.
I looked it up in Merriam, it said origin, unknown. HOWEVER: cur, from the 13th-century, can mean: 'a surly or cowardly fellow'. THEN: dudgeon , from the 15th, can mean 'a fit or state of indignation'.
Why so often an older man? Need we look farther than Dickens' Scrooge?
Look up some crazy sounding 20+ character word, takes three steps, and then you get a definition of the sub-sub-sub word and it says ".... blah blah, derived from the Greek base <abc>- and then also the Latin base -<xyz>", and you realize you had no chance at getting it from any kind of first principles or anything.
For what it's worth, the first two steps in your lookup would come naturally to a native speaker- it's a suffix formation similar to e.g. "cleanliness" and "friendliness".
"Curmudgeon" itself is interesting, because while it's not particularly common, I actually think a lot of native English speakers would recognize it because it's got a lot of character- for some reason, the way it feels to say and the way it sounds almost has some of the character of the meaning.
George Carlin, in my opinion, followed a similar arc. In the end he was just ranting for an hour. I appreciated his perspective (and delivery) but it was a lot more nihilistic, less funny.
If memory serves, Waterson said the later years were colored by his feelings from dealing with publishers. One of the most memorable comics for me is one where Calvin ends up in bed after resisting his parents' bedtime commands. In the final panel he bitterly declares that clearly his desires have no impact on his outcomes.
I'm sure it was also for his own sake/sanity. He took two ~9-month sabbaticals toward the last half, which was not the norm for cartoonists at the time.
