I have a real soft spot for Macendale Hobgoblin, which can mostly be attributed to the 90's cartoon (characters voiced by Mark Hamill seldom disappoint). I love the power hungry ones who never want to accept they're only second rate.
My favourite Macendale moment was probably back when he was Jack O' Lantern. During Gang War (I think) Tombstone (or was it Hammerhead? Apparently I need to reread my books) started firing at him and he just flew in circles going 'Oh my gosh, oh my gosh!' That's a tough as nails former mercenary if I ever saw one...
I also love how Harry defeated him in issue #312 and his sharp words to Hobby afterward.