The Classics

My art history teacher is the coolest guy I know involved with comics. (Excepting, you, Kevin.) He knows all sorts of facts and history; so he told me to read Pogo, only with annotations.
I'm halfway through the book, and I while admit that Pogo is good, I feel two messages communicated:
1) the comic is dated
2) Walt Kelly didn't enjoy what he was drawing.

I can understand both of my feelings, because this is a post World War II comic that ended in the 1970s; in addition, Walt Kelly lost countless newspapers every day and had to draw alternate strips for a while. The FBI even investigated him based on anonymous charges.
Kelly is an example of the comic strip rut, however: now that he had portrayed himself as a cartoonist of animals, he couldn't suddenly end the strip and do something else because he no longer found it fun.
And also, where is the silliness? Gary Trudeau, Frank Cho, and Bill Watterson all in their strips have an element of playfulness; Trudeau's recent storyline ventures into the ridiculous amidst with a Palin Barbie, lazy college students, and more! Frank Cho has pig smoking cigarettes and ducks playing with dachshunds.
Then again, is there a way to escape the rut besides to end a work? Or does it persist until the cartoonist dies?
Post up your opinions, people.
Next post is a Shoujo Beat review.