Round 1!

Heave Away

100

This adventure game's name might leave you expecting primates inhabiting an isle

Monkey Island

200

Davy Jones releases the Kraken in this 2006 film

POTC: Dead Man's Chest

300

This Straw Hat Pirate has the same first name twice

Tony Tony Chopper

400

In Sea of Thieves, a player is granted this title after reaching rank 50 with each Trading Company

Pirate Legend

500

In Assassin's Creed 4: Black Flag, the crew can be heard singing 'Leave her,  ______, leave her'

Johnny