There's no need to talk to the old man manning the cannon, so enter the building to the left. Return to Dread's ship and sail to Booty Island. You can repeat this process and win a vacation (which you can't go on) or some money (that you don't need) so you might as well not bother, especially if you're on your speed run. Walk back to the first alley, place your bet using the number and color you were told, and select the invitation to Governor Marley's party. Get the finger code right three times, and you're given the next winning number. Knock on the door and ask for the next number. If one finger is three, two fingers is one. So if four fingers is two, five fingers is four. 'If _ is _, what is _?' In case you didn't catch it, the answer is the number of fingers he holds up the FIRST time.

He'll go into an alley just past the library and get the next winning number from a man behind a door. You can try your luck (spoiler: you'll lose) or you can follow the winner and see what makes him so lucky. You'll see a game of chance being played and a contestant winning a nice bit of cash. You never know when you'll need a fishing pole, so accept his wager and walk into the alley nearer the jail. He's willing to bet his fishing pole that he can catch the bigger fish. Go out onto the pier and talk to the fisherman. Leave the jail and walk towards the waterfront on your right. Before leaving take the Manilla and Gorilla envelopes from the shelf and open them. Then give the bone to Walt the dog, pick up the key, and unlock your cell. Use the stick on the leg bone of the skeleton in the cell next to you. Lift the rock-hard mattress and pick up the stick from the frame underneath. This area has great music but you really should be going. Guybrush is invited to meet the Governor, but not in a good way.

Escape from monkey island lockup