hmmm this will be hard but for sure all are over 200hrs easily
1. Final Fantasy XI - easily the longest for sure since I remember playing this since it was beta on ps2.
2. Probably Civilization II - I've continued to play this game to this day and going through the entire cycle takes a long time and who knows how many countless times I've played it
3. StarCraft - logged a lot of hours playing on battle net back in college and still revisit the single player campaign to this day
4. Probably Auto Modellista - me and my brother would play online a lot up until their tournament of champions when hacks into the game became evident. A lot of time was spent on the single player as well to unlock cars and items.
5. Could be Baseball Mogul 96? I know I played this baseball simulator a lot and still play it to this day even, now that I think about it I am missing a lot of my old pc games but it could also be Pokemon Red/Blue I know for sure all the pokemon games logged over 100hrs but both red and blue contained all 151 pokemon leveled to lvl 100 the hard way so these could actually surpass mogul.
Final Fantasy VII, Xenogears, and Mario Kart 64 probably earn honorable mention
“When I was 5 years old, my mom always told me that happiness was the key to life. When I went to school, they asked me what I wanted to be when I grew up. I wrote down “happy.” They told me I didn’t understand the assignment and I told them they didn’t understand life." - author unknown
