The original category was “Game I’ve played more than 5 times.” There really isn’t any game I’ve played more than 5 times, unless you count playing through character stories in a fighting game. The original Warhawk comes to mind as a possibility, but I’m not entirely sure. I’m sure there are plenty of older games from the 8 and 16 bit days that I may have played 5 or more times, but I never really kept track of that kind of info. Saints Row: The Third is getting close, as I started my 4th play-through a couple weeks ago.
Everquest would be the easy answer for most hours. That total is well over a year’s worth of time just on one version of my main character. EQ2 comes in second with 3 hours shy of 185 days on my necromancer. Those kinds of hours seem normal for an MMO. Out of the rest of the games out there, I’ve logged the most hours into Supreme Commander with 200+ hours. I’m sure that will soon be surpassed by another game soon enough.