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May vs Risky Boots
Backgrounder (252)
Season 2, Episode 7
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Air date June 14th, 2015
Written by Ahomeschoolingroudon
Directed by Ahomeschoolingroudon
Episode guide
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Chris Redfield VS Dallas Kuro vs Vega

May vs Risky Boots is a What-If? Episode of Death Battle


Guilty Gear vs Shantae! Two female pirates face off in a battle of Hero vs Villain! Who Will Win!


Wiz: Pirates, the sea equivalent of criminals. And today we're putting two female pirates against each other

Boomstick: May, the anchor wielding pirate

Wiz: And Risky Boots, Queen of the Seven Seas

Boomstick: He's Wiz and I'm Boomstick

Wiz: And it's our job to analyze their weapons, armor & skills to find out who would win a Death Battle!


Wiz: The Jellyfish Pirates, they are a group of pirates who steal from the wealth and give it to the poor.

Boomstick: Then how are they pirates?

Wiz: I don’t know. But among them is the cheerful warrior May. As a child May lost her home and parents

Boomstick: But somehow doesn’t remember it.

Wiz: However she was eventually raised by Johnny, the leader of the Jellyfish Pirates. She gave her a new name May and gave her a new home aboard the Mayship..literally, it’s named the Mayship.

Boomstick: Can’t complain, with somebody like this it’s only gratitude. May wields a huge ass anchor in combat! Yet somehow she’s able to swing it around with ease thanks to her superhuman strength

Wiz: She can also summon aquatic animals such as dolphins and whales to attack her opponents.

Boomstick: Like Aquaman.

Wiz: With this May has been able to defeat foes such as Millia Rage and I-No. But after Johnny disappeared she was able to take leadership of the Jellyfish Pirates.

Boomstick: Yep, Aquaman ripoff or not stay out of her way

May: You messed with the wrong pirate!

Risky Boots[]

Wiz: The leader of Tinkerbats, Risky Boots

Boomstick: Her name is Risky Boots? Really?

Wiz: Yeah.

Boomstick: Well, whatever. Risky Boots being the self-appointed Queen of the Seven Seas searches for power

Wiz: Yep, while she’ll usually leave combat for her machines and Tinkerbats she’ll step in if need be. She carries around a Scimitar. A backsword with a curved blade

Boomstick: Why is it curved exactly?

Wiz: Beheading purposes

Boomstick: Oh ok...sweet..

Wiz: However for long range she has a Flintlock Pistol

Boomstick: Ah yes, guns. My only true love....what? Sorry I wasn’t thinking clearly

Wiz: Uh..right. However she can also try to take on opponents hand to hand.

Boomstick: With her wicked dive-bombs. However, I just want only one type of bomb wi-

Wiz: Boomstick no. She’s also quite durable being able to take hits from Shantae’s magic.

Boomstick: However, she has one major flaw. Despite her being able to take on opponents hand to hand. She’s..kinda defenseless when she does so. She wasn’t even able to combat a single Cacklebat without her Flintlock & Scimitar.

Wiz: But being dominating and deadly. Risky will take all that’s not hers

Risky Boots: Ho ho ho! No need for alarm! I’m just dropping by for this!

Death Battle![]

On an island the Jellyfish Pirates were waiting for a rivaling group of pirates to show up. The Jellyfish Pirates being led by May

May: They should be here any minute. You guys take out the Tinkerbats, I’ll deal with the leader.

The Jellyfish Pirates saluted. Then another ship showed up. The rivaling pirates have showed up. The Tinkerbats charged forward as Risky Boots exited the ship

Risky Boots: Ho ho ho! Get ‘em!

May: Time for the plan to fall into place, I’ll end the rivalry once and for all! For Johnny!

Risky Boots: This’ll take the cake.

Risky Boots pulled out her Scimitar while May pulls out her anchor and both get in a fighting stance


May runs up to Risky and swings. Risky however avoids and rapidly slashes at May. May however blocks

May: You don’t look so tough!

May whacks Risky back.

Risky Boots: Grr...

Risky Boots scowls and jumps up.

May: What are you doing?

Risky Boots: You have no idea for the trouble that’s in store.

Risky Boots strikes downward at May, slashing her chest.

May: Urgh! Close one!

Risky Boots: Thanks. Maybe I’ll end you quicker.

May: Was being sarcastic.

May summons a whale from the water and it attacks Risky

Risky Boots: Grr. Get away from me you cretin!

Risky Boots kicks the whale away and swings her sword at May. May swung her anchor at the same time and both struggle to empower each other. May however manages to overpower Risky and cracks open the sword

Risky Boots: No!

May: Alright! Here goes!

May gets her anchor ready and lifts it up in a striking position and runs up.

Risky Boots: It’s not that easy little girl! 

Risky Boots pulls out a flintlock pistol and shoots May. But May shielded the attack with her anchor. Risky shot again, this time for her leg. May got knocked down

May: Agh! No!

Risky Boots: I have won!

Risky Boots runs up and tries shooting May again but May summons a dolphin from the water and it attacks Risky before she fires the bullet

May: Back on track!

May got her anchor ready again and swung at her arm, knocking the gun right out of her hand

Risky Boots: No!

Risky Boots fought back by kicking May but to no avail. Risky Boots dashed away but charged back and divebombed her

Risky Boots: Take that, you deserved it with your ugly face.

May however grabbed May by the neck

Risky Boots: Ach!

Risky Boots fought back but couldn’t compete with May, she was left defenseless

May: This is for Johnny!

May swung her anchor down at Risky’s head. Breaking her skull. May dropped Risky’s body as she sees her crew has bested the Tinkerbats

May: Good work, we’ve finished the job


May and her crew aboard the Mayship and sail away as the remaining Tinkerbats flee seeing the dead Risky


Boomstick: This is actually the first time a hero trumped a villain.

Wiz: Well..

Annie Leonhardt bursts Fredrika’s brain

Remilia Scarlet cracks open Rachel Alucard’s neck

Killer Frost throws the frozen Sub-Zero to the ground shattering him

Wiz: Yeah, you’re right!

Boomstick: Anyway, this was a close one. While Risky was very deadly unfortunately when she was separated from her from the Scimitar & Flintlock she stood hardly any chance

Wiz: Remember, she couldn’t combat a single Cacklebat without them. So I doubt she’d be able to take on a superhuman anchor wielder.

Boomstick: And while Risky was better athletic wise, May seemed to have every other advantage. And she’s dealt with strong foes before like I-No and won. While Risky always seems to be defeated by Shantae

Wiz: The final nail in the coffin was the fact that Risky have much less combat experience as Risky always has her minions do the work for her and treats getting herself involved as a last resort

Boomstick: Well I guess that showed Risky’s thick skull who’s better

Wiz: The winner is May.

Next Time! (Ahomeschoolingroudon)[]

Boomstick: Next time on Death Battle...

???: Shakushi!

Two slashes appear.

Kuro vs Vega!