Hey, I finally made 100 edits. Pales in comparison to most, I'm sure, but I'm proud nonetheless.
I first got into Star Trek thanks to an awesome history teacher I had in 10th grade. He had us watch Star Trek movies (I - V) as a metaphor for human issues and topics. So I watched the movies before I saw a full episode of TOS. Then I watched all of TOS episodes, renting them one at a time from the library. Finally in college a friend of mine had me watch my first TNG episode, which was "Phantasms". I still think one of the funniest lines is Worf offering a slice of "cellular peptide cake with mint frosting."
I'm still working on this list, but here's a start.
The funniest episodes I love are: "Message in a Bottle"
From ENT, I say, what is this "Enterprise" of which you speak?