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If you look at the collection, it is apparent that they often group unrelated clipart into one picture. Therefore, the four icons, the penguin, the bow and the "comic" panel are likely completely irrelevant to each other. Despite being bundled with DOS software, the monochrome pictures are likely best suited for the Mac's high-res monochrome screen, and many seem to have been made by Mac fans mocking PC users in comics like these. They would hot have known about Tux the Linux penguin back then so it's a generic penguin.

As for how the comic is supposed to be funny, I'd guess that the point is how difficult setting up a PC used to be(?) No idea if the thought bubble with the pirate is relevant but it is in a dithered area, meaning it's likely not meant to be cut and pasted elsewhere.