Time travel back to October, 1985.
This one’s definitely evergreen.
This one’s in CIDU territory. She’s giving a reasonable excuse. What’s the joke?
Tough decisions, indeed!
To get the full effect on this one, you have to imagine that Princeton shirt in the brightest orange imaginable.
Comics I Don't Understand 
I’m not sure I understand the first but as to the “we’re entertaining” one, everyone in the background is studiously ignoring each other. One guy is reading a magazine.
The first one represents the days of the week.
@beckoningchasm, very interesting possibility — but in 1985 we weren’t working six-day weeks, mostly…
The “entertaining” one, though this surely was not the intention, makes me think of famous examples where the ambiguity is both structural and lexical, such as “Visiting relatives can be tedious.” In the cartoon, “entertaining” could be taken as “amusing” (an adjective, rather than present continuous tense) — but that doesn’t actually give us a pun-joke I’m afraid.
Interesting idea, @beckoningchasm. “2 And on the seventh day God ended his work which he had made; and he rested on the seventh day from all his work which he had made.
3 And God blessed the seventh day, and sanctified it: because that in it he had rested from all his work which God created and made.” (Genesis chapter 2, KJV)
First looks like a bald boss in sunglasses relaxing due to the work of his underlings who all have their hair and conventional lenses. There’s a hint of it being the reward for sliding along the corporate table vs. the usual metaphor of climbing the ladder.
I’m not sure I understand the first
Of course not. It’s from The New Yorker.