Speaking of simple Simons as I was a few days ago, how about Simon Belmont from the Castlevania series? Okay, the games don’t show him as simple, but his portrayal on Captain N made him totally arrogant and narcissistic, and always wanting to compete with Kevin. People have complained about his portrayal on the show, but I never particularly minded it. I mean, that’s what made him funny, or at least as funny as that cartoon ever got. But then, I watched the show before being exposed to the actual games. I guess if you’ve gotten the impression of this guy being a bad-ass vampire hunter and see that he’s been turned into a flamboyant egomaniac who always wears aviator goggles for no apparent reason, it could be a bit jarring.
Interestingly, his page on the Castlevania Wiki describes him as “rather brash and inclined to force his way through situations.” I guess that means he’s not supposed to be as selfish and cowardly as he is in Captain N, but it does hint at a certain level of foolishness. As for Simon’s animated get-up, this page speculates that the goggles might be an artistic (using that word loosely) reinterpretation of the headband he’s wearing on the box art for the original Castlevania.
He also wears a backpack that has just about anything he could want in it, even if it violates the laws of physics. In one episode he had a bazooka in there, and in another a unicycle. There’s a complete list of the contents here. This sort of thing is pretty typical for cartoons, and sometimes even live action, as with Mary Poppins’ bag.
His hair color has been been a subject of some controversy, but this was something that frequently changed for video game sprites.
Besides, the cartoon Simon was drawn to somewhat resemble his voice actor.
Simon’s level of competence varied, but I think there was a moral component to this. When he was trying to show off or chicken out of doing the right thing, he’d make an ass of himself; but when he helped out the team he could be a valuable asset. His whip was sometimes shown as having a mind of its own.
While Simon’s rather foppish personality has led some viewers to think he’s gay (sort of like Vanity Smurf and Rainbow Brite’s horse Starlite), he was consistently shown as having a thing for Princess Lana. Since she was more interested in Kevin, this led to much of the competition between the two. What’s interesting regarding Simon’s love life is that a 1988 Castlevania arcade game called Haunted Castle had Dracula kidnap Simon’s bride-to-be Serena at their wedding.
The game’s canonical status is somewhat up in the air, but we do know that Richter was one of his descendants, so he must have eventually had at least one child.
The infrequently updated comic Captain SNES, which I’ve written about before, has its own take on the Simon who appeared on the show. While the comic mostly accepts what was established on the show, the hero’s own attempts to reconcile the cartoon with the actual games he played have an effect on Videoland. Dr. Light and Dr. Wright are two different people, Mega Man being green is only temporary, and the guy with the goggles and the whip is actually Simon’s brother Simone Belmont (with a silent E). The story is that the original Simon is unable to join Lana’s army because he was cursed by Dracula (which of course is a plot point in Simon’s Quest), so he sends his brother instead.
After the events of the show, Simone betrays Kevin and traps him in the Mirror World, which he only escapes at the expense of Lana’s father’s life. Simone is banished, but he comes back years later to fight against the Sovereign of Sorrow, and presumably dies in the battle. The real Simon joins the bad-ass team known as the N-Forcers, but we still don’t know what happened to him. There has been some speculation that a mysterious figure in the mirror who talks to Cecil looks a lot like Kevin, so it’s possible he never escaped the Mirror World at all. And since we only have the word of the Kevin who came out of the mirror that Simone was a traitor, there could be more to the story.