Gaius James Rover is ready for success and adventure! After living with his uncle for many years, an opportunity to escape and seek his fortune has arisen. Using every last piece o' eight he owns, Gaius charters a ship and crew, and sails off to deliver a shipment of Jolly Rover rum - an addictive mixture of tobacco and rum, which is named after his father, a clown who died from an improperly loaded trick cannon hitting him in the groin. Gaius dreams to start his own circus, but his plans are cut short when his ship is hijacked by bloodthirsty pirates. Trapped on board their ship, Gaius must become a pirate himself if he is to escape their clutches and recover his stolen loot!

Jolly Rover is a point and click adventure game in the style of games such as The Secret of Monkey Island and King's Quest V. The game retains the classic 2D animated style of those games, while bringing in modern enhancements to prevent the player from suffering the problem of not knowing what to do next. It features a "Quest" bar, which indicates what you're meant to be doing currently to progress. Holding the space bar displays all the on-screen hot spots, while the text on an item will be blue if a new response can be given, and white if there is no new information for it. As with most modern point-and-click adventure games, Jolly Rover uses a "one click does it all" method of interaction.

The game also features a built-in hint system in the form of Gaius' companion parrot, Juan Leon. Juan stows away in Gaius' inventory early on in the game, and the player can talk to him to receive general hints on what to do next. If they're still stuck, they can feed him one of the many crackers found throughout the game, which will progressively give more detailed hints (with the final hint giving away the solution entirely). However, this hint system is entirely optional and doesn't need to be used if the player feels like a challenge.

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