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I'm not GP, but I've played a few adventure games and was very excited to try Monkey Island because of its sense of humor and style. But it felt basically unplayable to me (basically it felt like the only strategy was brute force), here's the puzzle that made me give up:

Give the jawbreaker to Blondebeard to loosen his gold tooth, then give him the pack of gum. When he blows the bubble with the tooth in it, pop it with the pin and the tooth will drop out. Get the gold tooth, then exit the shop. (To get the gold tooth on Mega-monkey, chew the pack of gum to get the chewed gum. Inhale from the helium balloon, use the gold tooth in the chewed gum and then chew the tooth in gum. It will float out the window of the shop and land in the mudpuddle outside. Use the pie pan in the mudpuddle to get the tooth).

4 comments

That’s not Monkey Island 2 (Monkey Island 2: LeChuck's Revenge), it’s Monkey Island 3 (The Curse of Monkey Island), which Ron Gilbert was not involved with (I believe).

That was the toughest puzzle in Monkey Island 3 for me, I remember being stuck on it as a kid for a long time, weeks maybe, until we read the solution somewhere, either a website or a game magazine. And it was the one puzzle keeping us from progressing to the next CD I believe. My father, not understanding english, was one to try every item with everything, brute forcing his way around, even he couldn't crack it. I think on easy mode this puzzle doesn't require all the steps. The other tough one was the dueling banjos, I think I had to write down the sequences on a piece of paper. It's still my favorite game ever, left such a big impact on me, from the intro music, humorous cut scenes, drawing style, the sense of wonder and excitement, everything was just perfect.

I remember that puzzle from Monkey Island 3. I mean, yes, the game is tricky but think about all the hints the game is giving you: „gold tooth“, „jaw breaker“ and I think in the dialog tree with Blondebeard you could compliment him about the gold tooth … and the mud puddle where you dig for gold using a pan like like gold diggers did in the clichés about the gold rush. So I mean it could be worse.

You get the hang for these kinds of puzzles once you played a couple of them.

On the other hand what I hate most in adventure games are random logic puzzles to open a door or find out where you need to go next. This is usually a cheap way to slow the game down. Lucas Arts was guilty of this kind of thing after Ron Gilbert left in „The Dig“, too, which still was a great game nevertheless.

The fun part is that puzzle you're describing is only in the optional Mega-Monkey mode where you chose to get more difficult puzzles at the start of the game. In normal mode, you can walk out the door with the gold tooth as soon as you get it.

You're describing a puzzle from the Curse of Monkey Island, aka Monkey Island 3. Ron Gilbert had no involvement there.