1) Rome Total War - I could play this for years, until I had wiped out the SPQR with every playable faction... 2) Tony Hawk Pro Skater 2 - this game was my first obsession, I could get a LOT of playtime just trying to master every trick and buy every deck and open every secret area. 3) Legend of Zelda: Ocarina of Time - Aside from being my all time favorite game, the number of minigames and sidequests would use up a lot of my boredom hours. and the main game itself isn't exactly lacking in challenges... imagine being able to play through the water temple without getting lost... it's a big job, but somebody's gotta do it. 4) Final Fantasy X-2 - There are a lot of different goals in this game. Multiple endings, getting 100% (which I never managed to get yet), all the dresspheres, every character leveled all the way up in every class, collecting items... You could play it twelve times with a different goal each time and not get bored. Although I'd get kinda tired of Rikku's voice by the end of it. 5) Sid Meier's Pirates - Plot your own rescue.

Enter the hall of shame. 1) Chrono Trigger. 2) Tony Hawk Pro Skater 3. 3) Final Fantasy VIII. 4) Legend of Zelda: The Minish Cap 5) Knights of the Old Republic (I or II).