This strip originally appeared in my 1993 book Black Cat Crossing. It was just kind of a lark, done (as pretty much all my work has been done) to amuse myself. I didn't really have any plans to use the character ever again.
Then in 1998 I began writing the graphic novel that would eventually be published as Mad Night. It was about a series of gruesome murders on a college campus and I wanted it to feature a fearless (i.e. somewhat crazy) female protagonist. I remembered Judy Drood and decided it might be fun to revive her. In Mad Night I wrote the character straight (well, as straight as I ever write anything) - that is, not jokey, not quite as broad. But I did use this original strip as her backstory and even alluded to elements of it in the book. (The backstory goes something like: As a teen she had been the stereotypical wholesome "girl detective." But finding out that her trusted father was actually a sort of deranged master criminal turned her angry & cynical & prone to see crime & corruption everywhere, even where it's not - which has led to occasional "problems" with the law. She cannot tolerate secrets or unsolved mysteries - it's pathological - she will solve them whatever it takes and has the absolute fearlessness of someone with nothing to lose). I know - it's nothing all that earth-shaking or original, maybe, but it's a lot of fun to write.
Also, I wanted to add: This strip was one of about thirty pieces I had hanging in a show back in 1997 at the (original, old) Cartoon Art Museum in San Francisco. At the reception my good friend Randall Ann Homan pointed to this strip hanging on the wall and said, "I want to read more stories about Judy Drood!". That definitely planted the idea in my brain -- so thanks, Randall!