Calvin used a fountain pen to do this which is Watterson showing his age. Even by the time I was in school fountain pens were long since out of regular use. I knew how this worked because I watched Tom and Jerry cartoons as a kid, and this very strip may have been some contributor to my developing an interest in fountain pens early in life.
Fountain Pens
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We used fountain pens in elementary school, and I'm younger than 30. Europe though.
Definitely not here in the US. In elementary and middle school the standard was the old #2 pencil, and teachers were already ranting at us on a regular basis for using gel pens in strange colors. By high school, I was literally the only person in the building who owned one and I used it to deliberately annoy one specific teacher. (A fountain pen, that is, not a gel pen.)
Even so, I'll bet you your fountain pen was a cartridge filler and didn't have a lever. Right?
Yes we filled it with a cartridge. That didn't stop us from getting ink everywhere 😅. Not as dramatic as the comic of course. I still have the pen. It still works as well, but the tip has been ground flat from so many years of writing. I guess I didn't have the lightest hand as a kid.
Knowing what I do of Watterson, he probably just really wanted to draw an octopus, but yes, Calvin’s school is coded as very “public” (in the US sense), and there would have been very little sanctioned pen use at all for a first grader by the late 80s. A fountain pen would have been out of the question. A lot of the C&H school vignettes are a little bit “out of time,” but this one is definitely not going for authenticity, LOL.