By classics I mean you oldies with the NES plugged in with that classic game Super Mario Bros still locked in. Ok, so you're not really an oldie if you grew up with those games but you still have a home court advantage when it comes to NES games like Super Mario Bros, Donkey Kong or Duck Hunt.
At least that was my observation I had a couple weeks back when I was asked to return to some old ****games and play Mega Man 9 (new game, old flavor). Even though this game required 2 buttons to press and a four-way directional pad to control the blue bomber I found it much more difficult than any other games I have recently played that requires a whole keyboard and mouse or a controller with X,Y,R1,R2,L1,L2, Z and maybe even a C sometimes. After flailing around on the Jewel Man stage I finally gave up the controller to my older cousin that had a good 5-6 years plus of experience on these types of games over me where he almost seemlessly defeated the stage and got to the boss. Even my older brother managed to one-up me on this stage but if I was weilding an xbox controller I would bet I could beat them at Call of Duty or Gears of War. Does this extra exposure to the older ****games give the older generation that grew up with those games an advantage on the younger generation? Does playing Mega Man come natural to you while you may struggle for a bit on newer games? Do you feel at home in 2D worlds?
Given, if I had more time to practice with Mega Man I could have done a little better but with just about the same practice time I had as my brother did it seemed much easier for him to do anyway.
In the summer of '05 I had another first hand experience of this before when I went on my own journey to beat all the Legend of Zelda games in the series. After beating Ocarina of Time and Majora's Mask on the Nintendo 64 I turned to my dusty (and slightly stained brown) NES to play the 2 original games of the series. To my surprise these were the most challenging of the two Zelda games to beat. Especially Legend of Zelda 2, if you've played that you can probably share my annoyance with Link's sword being just about the same size of his elvish ear.
Through my observations and own experiences I do believe the somewhat older generation that had a longer exposure to the NES will always have a slight advantage over younger generations even if they have played the NES before. Go back and play some old games and you will probably feel how the difficulty is much different to games today and you feel a lot more accomplished when you beat an old NES game as opposed to a Xbox 360 game. Plug in your NES or download them on your Nintendo Wii, (since it seems everyone in the world has one) they are releasing a lot of the classics onto WiiWare and prepare to shed some tears of frusteration.