I played Dragon's Lair once....worst 30 seconds of my life.
Best quote EVAR.
But in the spirit of the thread:
1) Watching a fat, balding, flaming red-headed (and I mean caricature beer belly fat like octo-mom pregnant redneck fat) Junior High School PE coach who also moonlighted as the HS driver's Ed teacher tally up a high score on Pac Man in a local 7-11 back in the day. I was 15, and although his name was Billy Burge, we called him Billy Barge. It broke my preconception of "cool." I spoke to him later in life and learned he was really a very cool guy. Still is, and I regret my childhood preconceptions. But. Imagine this with bright red in the hair:
Handily making you look like a n00b on one of your favorite games back in the 1980's.
2) Playing Red Baron for the first and last time in your life and having Dad tell me it's time to go when I still had all 3 lives. Back when I was like 14.
3) The worst? 1999, Florida, arcade in Sandestin mall, playing that tank/hovercraft game that had 2 machines linked and it was a lot like Mechwarrior but you had full 360 degree freedom with those two sticks and triggers, and not only beating my cocky son (at 17 he had some attitude) but also gaining his admiration....until the power dropped for a microsecond, not only wiping out my super high score, but rebooting the game and wiping out my credits. I would have towered over the scores that day, due to blind luck and just being in the zone as I had not been since 1986 on a Tempest machine in Washington DC - plus a combination (I realize now) of the machine losing high scores when the power surged at that arcade.
4) Freshman year, high school at Godfather's Pizza (being in Louisiana, our churchgoers often referred to that place as God the Father's Pizza, ha, ha) on a date, trying to impress a girl, and having never played Pac Man before - not knowing anything about the game and looking like a fool as other kids yelled mercilessly at me to EAT THE GHOSTS NOW!!!!! AWWWW, YOU WAITED TOO LONG YOU ARE DEAD.....
For those of you who grew up with video games in the home, you won't understand that last one - but what seems obvious today was often the fodder of cheap paperback strategy guides in the early 1980's. Hell, Time Magazine even wrote an article on Asteroids trying to grasp the allure of destroying little rocks that never hurt anyone. None of us back then knew how to play these games outside what was on the tiny instruction card. And we learned by playing and dropping quarters which would be the equivalent of about a buck fifty a try today.
Now get off my lawn before I turn on the sprinklers.