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I think there's a slight chance you might be overanalyzing his comment and taking it too literally. None of us actually sees "Rider down" and laughs. It's the audacity of the squid that makes them comical.
"YO DOGGZ CHECK ME OUT STUNTIN WITH MAH OAKLEYS AND MY FLIPPY FLOPPIES! YUT-UUH!"
"Hey, wtf, where'd my face go? Why me? Woe is me!"
If us picking on squids on the internet makes some kid put a helmet on, then we're doing more good than harm. Hurt feelings don't bleed, but road rash sure as shit does.