Even when I was a kid and mostly liked the good guys, I thought Bobby Heenan was hilarious. This, from the 1992 Royal Rumble is my favorite commentary. Fortunately it's been preserved on wiki quote:
(Roddy Piper saves Flair from a Jake Roberts DDT)
Bobby: I never thought I'd say this, but thank you, Roddy. It's a kilt. It's not a skirt, it's a kilt.
(Not long after, Piper attacks Flair)
Bobby: You no-good creep! You skirt-wearing freak! It's not a kilt, it's a skirt!
Sadly, in recent years Heenan suffered from throat cancer and has had most of his jaw removed.