As far as Watterson on Breathed, there’s this sketch…although I believe either Watterson or Breathed (I can’t remember if I first saw it in a C&H collection or a BC/Outland collection) has said it’s supposed to be good-natured ribbing about their differences on the commercial side of their art.
I disagree. The topic of this thread isn’t whether or not Breathed and/or Watterson is happy. The topic is whether they made the right decisions to quit or not quit.
So it’s on topic for me to post that I feel (and I think many people agree) that Breathed’s reputation has suffered because his recent work isn’t on the same level as his early work. Watterson avoided that possibility by retiring when he was still at the top.
MHO is simply that the decision that made each them happier over the rest of their lives was the right decision for each of them to make.
You feel that the impact on their lasting reputation or, more precisely, the impact on your opinion of their oeuvre, is what qualifies the decision as more right or wrong. Okay. YMMV.
Pretty sure that was published in a Bloom County book. Breathed and Watterson were friendly throughout their careers and up to the present day, and a lot of their exchanges were in cartoon form. Here’s a column about a Comic-Con panel that Breathed did on their correspondence. No examples given in the article, though, which is shame: I really want to see that Bill the Cat/Blondie mash-up.
I admire him a lot. A talented artist and a man of principle.
Anybody who loves C&H should see this documentary: Dear Mr. Watterson (2013) - IMDb
And read this book, which includes a lengthy interview with Watterson: https://www.amazon.com/Exploring-Calvin-Hobbes-Exhibition-Catalogue/dp/1449460364/ref=sr_1_1?s=books&ie=UTF8&qid=1488258485&sr=1-1&keywords=calvin+hobbes+catalog
Although he retired due to illness, I’d add Richard Thompson (creator of the brilliant, phenomenal Cul de Sac) as another who retired at the top of his game rather than allow his creation to suffer. For those who don’t know, Mr. Thompson had Parkinson’s disease. Anyone interested might find some interesting reading by looking into the relationship between Mr. Thompson and Mr. Watterson (and Stephen Pastis, creator of Pearls Before Swine).
And we may be able to add Darby Conley (Get Fuzzy) to this list, as Mr. Conley has not drawn any new daily strips since sometime in 2014 (although there are occasional new Sunday strips).
ETA: And yeah, I admire these guys for their work and for their desire to remain in control of their creations, even tho it means I don’t get to see any more new stuff.
Note he passed away a few months ago.
Calvin and Hobbes is one of the great comics. If you have spent 20 years doing high quality work and said everything you wanted to say, wanted to free up more time, and achieved your goals – a personal decision to stop may make sense.
Merchandising? Though many would do it without a second thought, and it would probably make the comic more popular… there is something to the argument of selling out, diluting artistic integrity, a pernicious aspect to advertising to children in general. Having a stuffed Hobbes or Calvin sno-cone machine is harmless enough. Having a Calvin movie would change how people view the work (even by assigning a voice to Calvin and Hobbes). Respect his decision? It is his decision to make.
Had? Oh, man, I didn’t see the news that he died. 
That guy did the illustrations in Joel Achenbach’s “Why Things Are” books, and I always thought his drawings went very well with the columns (much like Slug’s illustrations work well with Cecil’s columns, heh). Then when I started reading Cul de Sac I thought “Man, this strip is awesome … and it looks familiar.” Now I’m sad.
Aye; the “had” was deliberate. He passed away last July at just 59 years old. It was a very sad day for me. I remain quite enamored of his work. I’m pretty sure I own a copy of nearly everything he ever did with exception of some cartoons that only appeared in magazines, although I have quite a few of those too.
This is what I came in to say. How I loathe those fucking Calvin pissing decals.
I’d practically forgotten about them - used to see them a lot ~20 years ago, and wouldn’t have minded if Watterson had sued the hell out of whoever made them. But I haven’t seen one in years.
There is one other factor, or at least was, in the pre-Internet era where Schulz, Watterson, Berke Breathed, Jim Davis, etc. made their decisions to keep doing their comic strips or not.
And that was: each newspaper had a pretty limited amount of real estate that it was willing to turn over to the comics. So if Peanuts or Garfield kept on going, it meant that much less opportunity for new artists to break into the daily comics. Same with the prior generations of strips - Blondie and Beetle Bailey and the ‘uncomic’ strips like Rex Morgan, M.D. and Apartment 3-G.
Nowadays, of course, the Web has space for an all but infinite number of comic strips, but back then, it really was pretty much a zero sum game: maybe the artists were making the right choice for themselves in continuing their strips, but it choked off the entry of new talent, which was bad for the rest of us.
Seventeen years ago (!), The Onion noted the importance of these decals in U.S. society. 
I think the problem is that it wasn’t one big company that made them all and sold them, it was multiple smaller shops making them for a while, then going out of business while another took over. IIRC he spend a while suing companies who made them, but it would just put the particular companies he hit out of business, it wouldn’t stop the whole thing.
Taking this as a Fermi problem, I found an article saying that the Complete Calvin and Hobbes sold half a million copies from 2005 to 2010. It has a list price of $175, and Google tells me higher end royalty rates are on the order of 15% of list price. That works out to an annual income of $2.6 million.
However, that sort of royalty income doesn’t seem like it could add up to half a billion net worth, since I suspect it represents his peak earnings. Maybe the “net worth” includes the price he could get for selling copy and licensing rights?
Maybe. Given that Sturgeon’s Law still applies, think of how much total dreck we were spared.
No idea how they estimated Watterson’s, but it’s certainly possible that it includes estimates of the value of the movies, toys, and god knows what else he owns the rights to.
Like, imagine that J.K. Rowling didn’t license Harry Potter for films, but she still could. Her estimated net worth should include the expected value of doing so. A perfect estimation of her net worth might be exactly the same whether or not the movies had been made.
I remember reading something about Gary Larson deciding to cease The Far Side because he didn’t want “[his] characters shilling for Met Life” in ten years.
(Of course, what Met Life could do with Larson’s ubiquitous cow and duck characters is beyond me. YMMV.)
I don’t have problems with him quitting. But, with the merchandising, I can’t help but think of what additional value would be created. It’s not like he’d have to use the money selfishly for himself. Merchandise it but give all profits to charity and such. That would be the more admirable action.
As it is, I neither admire him nor don’t for this particular decision.
if I remember reading correctly didn’t schultz give away most of the licensing money to charities he had set up ? supposedly it was one reason he kept going for so long