I'm trying to find a game with longer loading times than Soldier of Fortune, Dreamcast. It has 12 levels with 3-4 loading times of 2:30 minutes each, in other words, 120 minutes waiting to playthrough it.
I'm tracking single loading screens only, not installation screens, world generation or games with lots of loading times (like Smackdown vs RAW) before something.
Other "classic long loading times" i've seen are not nearly close to this numbers. Games like Sonic 06 on 360 (around 40 seconds), Neo Geo CD games (Samurai Spirits RPG is the worst i've seen and its like 1:30 minutes), etc.
IIRC Mafia on Playstation 2 had those crazy 1:30 minutes loading screens in each bridge of the city, but, again, not nearly as close as SOF weird file packaging system.