An employee added some grid adorner code to the OOFILE report-writer engine, to draw borders around tables. It crashed the Mac every time he printed.
After an unknown time it was turned over to me to debug, being responsible for most of the report writer code - I was expected to have some magic insight.
It was only through very slow sing-stepping that I noticed that at one point he redrew a line on top of itself, rather than having more complex conditional logic deciding when to draw a line or not. On nothing more than instinct, I took that code out and it fixed the crash.
I came to the conclusion that the Laserwriter printer driver, which was converting Macintosh PICT drawing commands to a Postscript program, was unable to handle identical line segments drawn on top of each other.
Thats my funniest bug I can remember, in over 25 years. I can't remember what time in the morning I finally found the bug but I'm pretty sure my ecstatic yell set off a few car alarms in the adjacent park.