Bowser, Gannondorf, Sephiroth, Goldman. Video game antagonists have it made. They get to do all sorts of crazy shit like kidnapping princesses or setting hordes of zombies upon unsuspecting cities, then they just sit back in their ivory towers and send legions of undeerlings after you, when all you’re trying to do is clean up their damn mess. Occasionally they’ll show up and mock you in a cutscene or something, but it’ll take well over ten hours of gameplay before you can even throw rocks at the throne.

The thing is, far too often, the battle against the guy who made you jump through hoops for a week or more is less rewarding than that one crony from halfway through the game. So today, we’re celebrating the henchmen who made their careers in middle-management and ended up on top.

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Runner Up: Big Bob-Omb (Super Mario 64)

While I admit the struggle against the explosive regent isn’t exactly the most difficult thing in video game history (run behind him, grab, throw *but not off the stage*, rinse, repeat), the King makes this list for two reasons. One, his mustache is probably the best piece of digitized facial hair of all time, and two, he set the tone perfectly for the rest of Super Mario 64.

The feeling of getting to the top of that mountain, dodging boulders and water cannons the whole way, only to find his bulbous black ass waiting for you was mindblowing, and the feeling of hurling him off the stage, even if that’s not actually how to get his star, was all sorts of satisfying.

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5) The Scarecrow (Batman: Arkham Asylum)

Asylum was a wonderfully dark and intense title, and even though the Joker’s last hurrah was somewhat of a dud, the moments leading up to it were nothing short of phenomenal, especially Johnathan Crane’s fear toxin induced interludes. Things start off in line with the games’ other baddies, Batman walks into a wing of the ward, sees the aftermath of the Scarecrow’s dementia on a host of nameless guards and inmates and gives chase.

After turning a corner, however, there’s Jim Gordon, holding on for dear life against some unseen force.  Oh shit, Bats, we gotta make moves! Breaking into the next room in search of the commish, the Caped Crusader finds his friend slumped against the wall, stone dead. But before the grief, and the shock that Rocksteady would make the bold move of killing off Gordon can even set in, Batman turns the corner and… HOLY SHIT WHY IS THE SCARECROW EIGHT STORIES TALL? ‘Nuff said.

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4) Ramon Salazar/Salazar’s Right Hand Man (Resident Evil 4)

Miiiiiiiiiiiiiister Kennedy. The pint-sized castellan’s cackle will ring in my head for the next week because of this column, but that just further cements his legacy as a quality sub-boss. He has his own castle, two ghastly personal attendants and a fucking horde of brainwashed Spanish peasants who want nothing more than to tear the living limb from limb. And that’s just the tip of the iceberg for the ways Salazar finds to impede Leon Kennedy’s search for the President’s daughter. He’s got traps, dungeons and tentacled dogs for days too. Hell, even his garden isn’t a stroll through the flowers.

As for his right hand man, let’s try this on for size: he’s hulking, does tonnes of damage, comes out of fucking nowhere and pretty much can’t be killed unless you had the good sense to hold on to that rocket launcher for a rainy day and are perfectly accurate. Personally, I just ran from him during my first playthough, and it wasn’t until I got my hands on the Chicago Typewriter that I was able to put him out of his misery.

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3) Star Wolf (Star Fox 64)

That damn dirty ape Andross might be the mastermind behind the evildoings in Star Fox 64, but it’s his answer to the Starfox team that gives the game its most dynamic areal combat sequences. Unlike Peppy, Slippy and Falco’s general and utter uselessness, Wolf and his crew are competent pilots and are frustratingly hard to kill.

Pretty much anytime you manage to maneuver your ship behind them for a clear shot, they’ll immediately loop behind you and turn the tables, and like I said earlier, it’s not like your copilots are there to help. And to make matters worse, they’ll never fail to mention that time they killed your father as they blast you out of the sky. Nice dudes, right?

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2) Your Rival (Pokemon Series)

Whether you called him Gary, Blue, or Dickface, your rival was, well, a giant dickface. Oh, cool Charmander, bro, lemme just take this Squirtle. Cause that won’t be relevant down the line or anything. Even without a harem of cheerleaders or a convertible, your rival is still always in your business, challenging you to battles and shit when all you want to do is catch a few Pokemon and make it to the Elite Four at your own pace.

And when he gets lucky and beats you, he never fails to rub your nose in it; making things even more frustrating because you can’t exactly return the favor the other seven times you stomped his team. Well you know what? I’m glad your Raticate died. Jerk.

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1) The End (Metal Gear Solid 3: Snake Eater)

Yes, this character lacks the impressive backstory or screen time of most of the others to make the cut, but that doesn’t matter, because the long-range duel with The Father Of Modern Sniping is utterly flawless. Trudging through the muggy jungle trying to find any sign of the ancient marksmen while he’s busy taunting and raining death on your clumsy ass is maddening at times, but the euphoria when you catch sight of the gleam of his scope and put a bullet in his wrinkled forehead makes all the controller-throwing frustration melt away.

Couple that with the variety of ways you can move to the next level, including one of the cooler Easter-eggs in gaming history (he dies of old age if you set your console’s internal clock forward a year), and you have one of the best fights of all time. The end.

- Pool Captain