3 hilariously outmatched supervillains who were supposed to be major threats

While we’ve talked before about how some iconic supervillains started out painfully goofy, they at least managed to outgrow their role as just another in a long parade of unitard-wearing freak shows that paraded through comics in the ’60s and ’70s, a time when every supervillain apparently shopped at the Disco Clothes For People Who Are Also Evil and Colorblind store.

The true crime here is the crime against fashion. Also, all the murders, I guess.

However, it’s time to talk about the opposite: supervillains portrayed as legitimate, dangerous threats despite being so comically out of their depth that a legless turtle would have a better chance at beating the hero. These are villains who, for one reason or another, thought it’d be a good idea to antagonize a super-powered vigilante when at best they should be shaking down lemonade stands for protection money.


1. The Psycho-Pirate

Long-time fans of DC might be scratching their heads at this entry, as the Psycho-Pirate is a long-running and fairly competent enemy of the Justice League who has the power to inflict crippling emotions on his enemies with the use of a magical item called the Medusa Mask (he’s also loonier than a bag of rabid raccoons due to being one of the few people who remembers the original DC multiverse, but that’s beside the point). While the ability to manipulate people’s emotions might sound more like a developmental disorder than a superpower, you’d be surprised how effective it can be even against heroes like the Justice League. Turns out super-powered heroes aren’t exactly the most emotionally stable people.

Because what screams “psycho” and “pirate” more than a theatre-themed costume?

So if he’s this dangerous, what’s the problem? Well, because this isn’t the original Psycho-Pirate. The Pirate most comic readers are familiar with is a man named Roger Hayden, who was once the cellmate of the original, a man named Charles Halstead who debuted in 1944 as an enemy of the Justice Society. And more importantly, this version had no superpowers whatsoever; he was just some jerk who committed crimes based on inflicting emotions on his victims because he was jealous of his boss, which even for comic books is a pretty weak motivation. Just to clarify, a guy who literally commits crimes in the hopes that his targets will feel a certain emotion was facing off against a team that at the time consisted of heroes like Hawkman, Starman and the Spectre AKA the personified wrath of God.

Sure is lucky there isn’t a world war happening right now, so we can waste time playing hide-and-seek with ol’ Walrus Mustache here!

Laughably, Halstead would fight the Justice Society twice more (apparently, they didn’t wise up the first time and just not bother showing up for his weird little head games) before landing in jail for good, where he eventually died, but not before passing on information about the Medusa Mask to Hayden. Yes, somehow he knew it existed but never bothered to go find it. Sure would have been useful when he was running around trying to emotionally cripple the Justice Society, but hindsight is 20/20.

“Oh, if only every choice I ever made hadn’t been incredibly stupid!”

2. Big Man

As a street-level hero, Spider-Man spends most of his time dealing with purse-snatchers, drug dealers, and the occasional organized crime racket (though admittedly, that’s not quite as common as when he started out and New York City was basically just Mad Max with polyester instead of leather), with actual supervillains serving as his biggest challenges. Unless you happen to be reading the early comics, when Marvel for some reason thought that a non-powered mobster could serve as a genuine threat.

Yes, me and these three guys can surely force the entire NYC mob to obey us.

This happened to be Big Man, one of the earliest foes Spider-Man ever fought. Big Man, alongside his three Enforcers—Fancy Dan, Ox and Montana—decided to try and form a crime syndicate by beating the hell out of the various mob bosses, which for some reason didn’t just start a gigantic gang war. With New York undergoing a crime wave (though in the ’60s, how could anyone tell the difference?), Spider-Man was hard-pressed to put a stop to it. And by hard-pressed, I mean “beat the holy hell out of everyone the second he tracked them down.”

“Curses! My plan to set up a crime syndicate in the most superhero-packed city in the world has failed!”

Despite the story hyping up the threat that Big Man and the Enforcers posed, the writers clearly knew the fight would last about as long as it took Spidey to tie his shoes, and mostly spent the issue having Spider-Man try to figure out where the hell the villains were hiding (at the time, New York was apparently like 90% abandoned warehouses). However, the real kicker came after Big Man decided that his plan probably wasn’t going to work out and hightailed it out of there with Spidey losing track of him. Upon returning to the Daily Bugle, Peter finds out that the friggin’ cops had figured out Big Man’s real identity in the meantime, and it was this asshole.

…Don Knotts?

Big Man turns out to be Bugle reporter Frederick Foswell (J. Jonah Jameson really needs to start doing background checks on his employees), a shrimpy guy who wore shoes with lifts and bulky clothes to make himself look more physically intimidating as Big Man. Yeah, Spidey was supposed to have trouble with a guy who literally stuffed his own clothes to look buff, and even worse, didn’t even manage to catch him! Imagine if the Fantastic Four ever defeated Dr. Doom and he just turned out to be two nine year olds under that cloak standing on each other’s shoulders.

3. The Boomerang

Boomerangs have a surprising amount of popularity in the world of comics. DC has had no less than two Captain Boomerangs fighting the Flash, which seems like kind of an unfair pairing, but it’s not those two I’m going to be talking about here, because they can put up an actual fight. No, I’m talking about a perennial Spider-Man foe called the Boomerang. Boomerang is a former baseball player who got blacklisted for accepting bribes and ended up being recruited by the Secret Empire as an assassin. Jeez, at least all Pete Rose did when he got busted was hide in his house and unplug his phone.

At least now we know what Barry Bonds will do when they finally blacklist him for steroid abuse.

Despite being limited to throwing a variety of sharp sticks at Spider-Man, Boomerang actually performed pretty well against him. Not Doctor Octopus well, but that’s a rather unfair standard to hold a villain to; not many characters reach that perfect blend of megalomania and personality disorders. So why is he on this list? Because he didn’t start out as a Spider-Man villain. He was originally an enemy of the friggin’ Hulk.

“Maybe I shoulda started out against Hawkeye.”

Don’t let the even-more ridiculous costume fool you; that is in fact the same character. After being outfitted by the Secret Empire, the Boomerang’s first mission was to tangle with the Hulk. Surprisingly, a bunch of gimmicky toys didn’t work very well against one of the most powerful beings on the planet, and Hulk proceeded to smear Boomerang across the landscape. When Boomerang returned a few years later, the Secret Empire had collapsed, and he was now freelance-murdering. Over the years, Boomerang would tangle with several other Marvel heroes, but he mostly stuck to fighting Spider-Man, although he eventually found himself facing the Hulk again. He hadn’t gotten any more immune to having his spine tied in a knot in the meantime.

Thank god for the Comics Code, or Boomerang would be crapping out his own skull right now.

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