I think what you have to understand coolest, is that games age, technology advances, pinpoint perfection gets closer and closer to reality on home consoles and everything beyond the last 5 years is out dated.
But you do have a point though, some games aren't timeless, for example golden eye, so they shouldn't be ranked as such (many people put it in their top 20 all time greatest games list).
But I think you're wrong with OoT, it's only boring because we've played it again and again over the last 10 years under different names (some not even called Legend of Zelda). But you can't fault the gameplay as much as you can fault it graphical or in terms of story depth. But you're entitled to your opinion, so you're not technically wrong (I just think you are).
So I think judging older games overall is flawed, the only thing you can really critique them on is gameplay, and OoT, Super Mario 64, Tetris and Half-life are as tight as they come, you can't fault any of their fundamental gameplay.