Probably the funniest astro-story I ever heard was related to us by the director of our observatory, Artie Hatzes. And it concerned Mick Jagger (THE Mick Jagger) paying a surprise visit to McDonald Observatory, Texas. It involved a lot of " "Mick Jagger is coming up." "Haha, yeah, right, I can pull my own leg... ZOMG THAT'S MICK JAGGER!!!"
Though for perfect comic effect, one should have made a video tape of this and put it on Youtube, as it involved a lot of ridiculous facial expressions and guffaws.
Another cool McDonald Observatory story is the guy who got laid off or something and put a bunch of bullet holes into the 2.7m telescope's main mirror - it didn't shatter, just reduced reflectivity a bit.
Many years later, that was the one thing George W. Bush was really interested in seeing.