Oh man, don't get me started on Devil May Cry, That first moment when you encounter the Shadow was so my worst moment for me, I started panicking and well uh, ended up getting eaten and seeing one of the many dante death scenes..
I hated that airplane scene so so much. When the heck did Dante learn to pilot a plane, and shut up Trish. Your voice is like nails on a chalk board. I hate when Trish busts into his office, smacks him up a bit, then dangles her boobbles in his face to convince him to go. Why is this bish wearin sunglasses at night? I hate Trish in this game. I don't like that Dante has the magic ability to throw fire dragons. I don't like that Dante cried over Trish. I hate that Dante was a total freaking nitwit. I hated seeing that giant bird guy getting smashed to death. I hated those puppets because they were spooky scary. Most of all, I hate that Dante was just gonna leave "dead" Trish to guard his half of the key to the demon world, on a island that demons were popping out of and could very easily get a hold that amulet. I hate that he left Sparda's sword next to "dead" Trish on an island that demons were popping out of and could very easily get the sword and gain the power of Sparda. I hate that whoever touches that sword automatically gets Sparda's powers; but that has been with every game so whatevs, at least that is something consistent. This game is bad, real bad. But there is so much nostalgia and it's where the story of our favorite demon hunter began. So I can admit that it is bad but I still love it and play the poop out of it.
Urgh, my worst moment actually comes from the prequel novel (now non-canon) to DMC1. Dante referring to Eva as mommy despite being as grown*** man.
As for the game itself; nothing I really thought of as the worst moment (swimming and Nightmare aside), but the fact Trish throws a sword threw Dante's heart and attempts to throw a motorcycle at him yet he doesn't question he alliances when she says she's good. WAT?