I once received a custom chess set when I was about 10 years old. It was a classic design but we had it custom made and glass was hand blown and pieces had little things different (like custom paint, or pawns had faces and swords) it was all in the details. When I opened it Xmas morning about 85% of it was smashed to pieces. That was probably the worst I received.
The best I ever gave was to my mom a few years ago. She love Lucille Ball and I found this awesome purse and wallet online at some random store that I've long since forgotten the name of and grabbed it immediately for her. When she opened the wallet she was thrilled. Then she opened the bigger box that had the purse and went nuts. She was worried that it would be too heavy though and I said we could exchange it... it took her about 2 minutes before she opened it and realized the weight was from a few I Love Lucy DVDs I stuck in there and some chocolates
She was crying happy tears. I've never come close to being that good at another gift.
And because holidays are always a downer I once spent $75 on an antique bracelet and hat for this girl I was talking to and the day after giving it to her she broke it off and became a crazy whore. That was fun.