5 of The Most Ridiculous & Bizarre Retro Boss Battles


Toasty – Spyro the Dragon

The first boss in the original Playstation 1 game Spyro The Dragon, Toasty cuts a rather menacing figure – that is, until his true identity is revealed.  Spyro is confronted by what can only be described as a pumpkin-headed-scythe-wielding shephard. He is guarded by dogs which are arguably more intimidating than he is, as they dive through the air and attempt to make a dragon pancake out of Spyro.

After defeating two waves of creepy-canines and attacking Toasty twice, his menacing robes go up in smoke and reveal the true madness within – a sheep on stilts. I imagine this sheep was tired of being told what to do and wanted to take charge of the situation.

The boss fight all in all is rather straight forward and doesn’t last very long, but Toasty makes this list as he is truly memorable and a shining example of humour within a much loved video game.

Conker’s Bad Fur Day – The Great Mighty Poo

Perhaps one of the funniest boss battles in all history, Conker goes toe-to-toe with a giant singing turd. Conker’s Bad Fur Day for the Nintendo 64 was originally intended for a family audience but the game was redesigned and remarketed to suit an older demographic. The game features graphic violence, sexual themes and strong language. The Great Mighty Turd took full advantage of these facts.

The boss greets Conker by bursting into song, with lyrics filled with swear words and toilet humour. Conker must defeat him by throwing rolls of toilet paper into his mouth, which he promptly chokes upon before blurting out a new verse as he becomes increasingly angry.

The Great Mighty Poo doesn’t hold back when it comes to trash talking and he does so with a certain eloquence that makes this battle thoroughly enjoyable.

King K.Rool – Donkey Kong Country

Now, King K.Rool definitely had it coming when he stole Donkey Kong’s banana hoard. After leaping, rolling and being blasted out of barrels through all the levels, the showdown with King K.Rool will test your super-human reaction abilities one last time. Cannon balls rain from the sky and the reptilian King repeatedly tosses his crown at our favourite ape.

Once King K.Rool is “defeated” the credits begin to roll. I distinctly remember the first time I defeated him. I jumped for joy and punched the air and mocked the dead king, and as I was about to complete my victory dance, what I saw made me freeze: “THE END?”

Nope, it wasn’t the end. King K.Rool sprang back to life and killed me, as I was not armed with the controller. It felt almost like the developers of Donkey Kong were saying “you thought we were cruel, how’s this for size?” with a final brutal trick, reminding me to never let my guard down again, unless I know it really is over!

I am sure I am not the only Donkey Kong player who fell into the final trap! Kudos to the Devs for being so merciless.

Burt The Bashful – Yoshi’s Island

Yoshi’s island is another SNES classic that provides us with a humorous boss. Burt The Bashful is a large blob-type entity  whose striped pants essentially function as a HP bar. He’s the first boss to appear in Yoshi’s Island in “Burt The Bashful’s Fort.” Originally he was a regular sized “Burt” but Kamek’s magic see’s him grow into a giant!

Burt The Bashful is a simple boss. He bounces around and tries to flatten our dear Yoshi. Yoshi must throw eggs at Burt to lower his health while avoiding being squashed. With each egg that hits Burt, his pants get lower and lower and eventually disappear. Poor Burt blushes a deep red and proceeds to replicate a deflated balloon as he flies off the screen in embarrassment.

The amusing conclusion to the fight leaves you with a smile on your face and perhaps a little sympathy. Burt The Bashful was certainly a bad guy, but not bad enough be immune to the  shame of being caught with his pants down.

The Bobbins Brothers – Plok

The Bobbins Brothers are perhaps some of the most bizarre looking characters to set foot in a SNES game, with a pair of lips for heads and plump bodies. Their strange appearance is a big contributing factor when it comes to pointing out “ridiculous boss battles” as well as the manner of the fight which is basically “throw your limbs and pray you survive.”

Upon engaging The Bobbin’s Brothers, they will begin to leap around the screen and spew what looks like sharp teeth in Plok’s direction. The soundtrack for this battle adds a sinister layer to the fight and can be somewhat off-putting.

Some gamers consider this boss fight, which is the first, one of the most difficult in the game as it requires intense button bashing and immaculate positioning to defeat. The Bobbins Brothers are certainly a pair that aren’t easily forgotten!

While it’s always great to have a deep and engaging video game, sometimes it’s a nice treat to see something goofy pop up.  Retro games did this incredibly well, and because of that, they’ve managed to be memorable long after their time has passed. What Retro boss battles stand out in your memory? Do you think modern games developers should take heed and add more humour into their games?