The proudest moment to me would be when I got my paws on Bubble Bobble. It was during the C-64 era and a good friend lent me her copy. I only had about a week to beat this 100 level game which was quite a challenge. I didn't think that it would be possible since my skills with Arcade platformers on this machine have been mediocre at best.
Which personally I blame it on the use of Joysticks. So coming home from school every afternoon I tried to beat this game. After doing my homework of course!
Thinking back this is also something to be proud of! :-p Until one day previous to where I had to return the game to her I finally managed to get past the dreaded level 67. This I was very proud of, but this wasn't the whole story! I even managed to lose exactly 1 life and when I finally had to face Baron Blubber my hard was racing. Heavens, was I proud to have beaten that game!
Another proud moment was when I was able to beat Ring: The Legend of the Nibelungen. Don't ask how many weeks this has taken to figure all those weird puzzles out. Reason of being proud to have beaten it is that I managed on my own without looking up the solution. Many times I was very close to open the manual and see what the heck I was supposed to do. Think of this game as a Myst-like game with some ludicrous puzzles such as the one I clearly remember: Make the rainbow bridge appear, a clever puzzle, really. One you have to pay attention to music playing in the background. But figure that one out when you got no other clue available?
This was about the same a-ha! moment as when I found out what it was I had to do in one of the Deponia games. I don't wish to spoil it so let me just say that it's also got to do with music. -
There are several other proud moments, big and small ones, which I would like to share here - contest or no. For instance when I played The Last Ninja 2, there is this sewer level, there is a crocodile at the end of it moving in and out. My idea was to jump over it to reach the exit - which was clearly wrong of course. Each time I tried to jump over it would this beast eat me ... It must have been some weeks until I figured out that a molotov cocktail would be the solution ...
A rather more recent moment of pride was beating Risen, 100%, picking everything up, killing all enemies and monsters, doing all the quests in their correct order at the highest difficulty level, without dying once. Okay, no, that's not quite right. I had to use a Titan weapon to beat the final boss, sadly ... So 99% melee/fist-fighting and kickboxing all monsters and 1% beating the boss with the spear I guess I used? All this done from memory and a recording of it to proof it happened.
Longplay Most of what I take pride in is beating a particularly tough game and there were many such over the years. Some I only just this year managed to finish in a way that's not just barely managing to stay alive or avoiding tough spots. One of them is Wizardry VIII which I was proud of because it has taken me several times of starting and then being so overrun by enemies - I guess by virtue of playing it on the hardest difficulty also - not Iron-Man (never tried that), that a series of successive fights has taken almost an hour and sometimes more ... I guess the same is true with Gothic II which I was able to beat some days ago. I wouldn't say that there is much pride in there because it all comes down to level only one stat and a couple of abilities and going about doing quests and tasks in a particular order. The rest is child's play. :-)