Broken Base: The portrayal of Dante in TAS is a point of dispute for fans. While some liked it for changing him into someone who was somewhat more realistic while retaining his coolness and badassery, while others felt it made him as being Out of Character.
One of the main points explaining why it is canon is that it depicts how Lady and Trish first met. That is why they seem well acquainted in Devil May Cry 4.
He Really Can Act: Reuben Langdon (going under the alias "Justin Cause") does an impressive job of voicing this iteration of Dante, which is particularly notable given that, as noted under the Broken Base section, Langdon had not portrayed Dante as he was in first game when he didn't have some the quirks he is known for now.
Magnificent Bastard: For what he lacked in strength, Sid definitely made up for in guile by using Dante as an Unwitting Pawn in helping him collect the necessary objects for the ritual to acquire the power of Abigail.
The Woobie: Isaac from Episode 5. At first, he seems like the standard jerk you'd see on this kind of show. Hitting on Cindy, the waitress. But when he hears that he should be more like Dante, he starts becoming obsessed with Dante, to the point of repeatedly injuring himself trying to find Dante's secrets. As it would be to any normal person, he starts believing Dante's dangerous, and puts himself in greater danger trying to prove it. Thankfully, however, Dante chooses to help him out, and he gets the girl by the end.