I'm not old enough to have seen Jacques Plante or Ken Dryden. That caveat aside, I voted Roy without hesitation. As a Wings fan, he was a player you hated to play against, but you couldn't help but admire the talent (and more than enough confidence to go with it).
But even before any friction had built up between Roy and the Wings, my brother and I grew up playing borderline unhealthy amounts of NHLPA 93 on Super Nintendo. And whenever we wanted a serious game, he was always the Rangers, and I was always the Habs. Killer matchups, but part of the schtick was that the game had VanBiesbrouck listed as the starting goalie for New York, instead of Richter, despite Richter being clearly better. So I was always confident with having Roy, but it was a game within the game, for whether I could score on Beezer before there was another stop in play (because back then, you couldn't just take a timeout to change your goalie). Good times... Even if Mike Gartner had an impossibly hard slap shot.
) was one of the parts that made that team exceptional (literally) and without Roy, there would be no cups in 86 and 93. My heart says Dryden, my brain says Roy. Heart won 
