The absolute worst outlines were the so-called Special Talks. Many years ago, they were actually a manuscript, meant to be read, although I never allowed mine to sound that way.
I always exercised nearly absolute control over the outlines I received, going over them carefully before accepting them. Recycled circuit overseer outlines offered the most freedom.
Although, I couldn't give any of those talks with a straight face now, the old talk on the book of Proverbs, illustrating the difference between knowledge, understanding and wisdom was a favorite. "Is This Life All There Is?" had some possibilities. "Harmony of the Gospels," comparing the distinct purpose of each of the four accounts, the point of view, etc. Many were surprised to learn that there was a difference between Matthew and Luke's list of Jesus ancestry. (No, it was not just that one went back only as far as Abraham, while the other went all the way back to Adam.)
My last few years as a JW, the best talks were the shortest ones.