For me, funniest moment was when Terl (the boy who delivers bad news to Anomen all the time) showed up in middle of Beholder lair! He walked past all deadly beholders... to Anomen and... to my despair Anomen left when he heard his father tried extract revenge for Moira and got killed... he left... and we were about to fight like 10 beholders??? I was thinking "should I laugh or cry?"
My funniest moments with Terl came from the bug that has Anomen speaking the line about someone approaching over and over without Terl spawning.
The line is something like, "Wait, one approaches..." and he says something about recognizing him or being familiar.
"Wait, one approaches..." yup, it's an Elder Orb.
"Wait, one approaches..." Mindflayer.
"Wait, one approaches..." Saemon Havarian in Spellhold(this one gave me the giggle fits for a good half hour)
but the best was...
"Wait, one appraoches..." and it was a squirrel(or some other little animal) in the Umar Hills
In my most recent install, I must have mucked something up. I got to the encounter with Rylock (the poisoned guy you have to bring to the Harpers). Smack dab in the middle of the group of thugs, there stood Suna Seni, just chillin' while we were being attacked. I talked to her, and sure enough, she was convinced she was in the CC.