Worst...in what way? Frustrating? Aside from trying to S Rank all of Trauma Center (hey, I'm 5 missions away), it's when I missed the final B License Gold time in Gran Turismo 3...by 1 thousandth of a second.
Oh, and Burning Laps in Burnout Revenge. Fuck. Even Criterion knew they were too hard on the PS2, the Gold times got pushed up for the XBox360 version. But I'll get them all on the PS2 yet.
Saddest? Well, most of my games aren't too story driven. But, I'm the type of person who thinks too hard about his games. And, well, when I met my rival in Lavender Town in the Pokemon Tower, where he questions why you're there if none of your pokemon died, and he's suddenly missing his Raticate, it made me wonder how he lost it. Maybe it was...my fault.
You know, Pokemon Black and White could have had an AMAZING story if they actually made you think about whether capturing and fighting Pokemon really was right. And either way, you'd beat Ghetsis, but you'd either fight N, or work with him to create a world where Pokemon really are free. But I'm idealizing again. That'll never happen as long as Nintendo can keep milking money out of it. *sigh* But, I'm rambling.
Other bad moments...when I played Digimon World: Data Squad on the PS2 after being on a Digimon rush, having watched the excellent 3rd and 4th seasons, Tamers and Data Squad...only to find that the Data Squad game was just god-awful. The combat was shallow, there was no map for the area you were in, random encounters would pop up every five seconds, and everything, attacking, registering a hit, showing the next attacker, going to a new screen, pausing, accessing your ITEMS, everything, took a good 5+ seconds to load, at the very least. Meaning it took forever to do anything. Being intolerant of RPGs, anyways, this just really put me off of Digimon games.