Great Failures of Villainy, Volume One

When you think about the great, lasting villains of comic books, a few names come to mind. Doctor Doom, with his egomaniacal genius and melodramatic speeches; Magneto, who went from a goofy villain in a purple cape to a complex character with a morality twisted by a need for revenge; and of course, the Joker, whose bright colors and permanent smile would be creepy even if they didn’t stand in direct contrast to the dark, grim hero that he battles against.

You do not, in all likelihood, think of this guy:

 

 

And there’s a pretty good reason for that.

Say hello to Sylvester Sepastopol, folks! And yes: He’s a teenager, despite the fact that he has the bearing and combover of a middle-aged insurance salesman. First appearing in the pages of Teen Titans #19’s “Stepping Stones of a Giant Killer”–conveniently reprinted in second Titans Showcase–Sylvester here was the brainchild of writer Mike Friedrich, who brought us the pure genius of Vampires on the Moon, and the artistic dream team of Gil Kane and Wally Wood. And really, with a legacy like that behind him, how could he fail?

As it turns out, he manages to pull it off pretty spectacularly. So here’s how it all goes down:

Sylvester doesn’t have an origin as much as he just shows up one day on page one looking for The School of Criminology, which appears for exactly ten panels and is then never heard from again, despite the fact that it has the truly awesome distinction of being run by someone called Headmaster-Mind:

 

 

One assumes that unlike other Schools of Criminology, this one is devoted to the practice of crime rather than the study thereof, but that’s pretty much left up to the reader to suss out from the fact that Sylvester rolls in there and announces that he’s got a plan to destroy the Justice League, as seen above.

Sadly, the Headmaster-Mind doesn’t have time for a kid with a dream of world domination, and thus, Sylvester’s quite literally given the boot. However, despite his age, Sylvester isn’t the kind of guy who gives up easily, and resolves to make his own way in the world of Super-Villainy, finally learning the lesson that Will Smith struggled so hard to teach the children of the ’90s. Take it from me…

 

 

Adults just don’t understand!

 

Yeah, yeah, it’s actually parents. I know. Anyway, a few pages later, Sylvester’s plan goes into action as he uses the time-honored tradition of sending his “hang-ups” to the Teen Titans to lure them into a trap. Said hang-ups?

Campus Nazis!

 

 

Given that there’s nothing the heroes of DC Comics like better than busting up a couple of Ratzis, the Titans are quick to roll out in full force, but it’s never really made clear whether that actually happened, or if it’s just something Sylvester made up or orchestrated as bait.

Either way, it works, and once the Titans put the kibosh on the fighting, which includes Wonder Girl making the best joke of her entire career…

 

 

…Sylvester easily lures them into his secret lair, where they are promptly conked on the head via reversed gravity, tied up, and threatend with death at the hands of a genius gone mad.

This, for the record, is where Sylvester’s plan goes completely off the rails.

Why? Because this is where he decides to adopt his own villainous identity, and while I could explain how it all goes wrong, I think you’ll be able to tell for yourselves. Behold! I give you… Punch!

 

 

Man. Where do you even begin with this thing?

I’ve written extensively about the steps one has to take in order to ensure success in the world of diabolical schemes, but it never even occurred to me to advise against a ruffled collar and matching dunce cap. I just assumed it was a given.

And that’s even before we get into the fact that the whole “Punch and Judy” thing really only works when there are two of you.

As should be expected, Sylvester’s brief career as a super-villain is all downhill from there. Because really, you can have all the teleporting belts and anti-gravity rays that you want, but as soon as you slip into your thoroughly researched 14th century jester doublet, there’s really only one way things can end.

 

 

So ends the brief, ill-concieved criminal career of Sylvester Sepastopol, and we at the ISB salute him, if only for the fact that he was able to make even Robin’s costume seem like a respectable set of threads.

 


 

BONUS FEATURE: The ISB Picture Quiz!

Sylvester Sepastopol or a young Stephen Colbert?

 

 

U-DECIDE!!