The category was "Playboy Bunnies": What federal judge was a Playboy Bunny prior to going to Harvard and going into the legal field?"
Now, we had no idea (I know I've heard about this person, but I just couldn't pull her name), so I wrote down "Judge Judy, and please pluck out the eyes in my brain NOW!" just as a joke answer. It got a laugh, but even I had to admit that the best joke answer of the night was:
Spoiler
Janet Reno.
I nearly fell off my chair laughing.
Oh, the real answer:
Spoiler
Kimba Wood