9. Anchors Away - Grim Fandango
In Grim Fandango's boat section our hero, Manny, discovers criminals have hijacked his vessel, forcing him to hide in the engine room.
To escape, Manny must hoist and drop the anchors at specific points, and then use the lever to turn the ship at a certain angle. If you do this correctly, the anchors will get caught in each other. If you try to reverse at this point, the ship will break in two, allowing you to flee.
If you find this whole ordeal too confusing, you'll probably consult a walkthrough. (There's no shame in it. Grim Fandango's puzzles are so illogical, the average gamer has a guide ready at all times while playing it.)
However, guides aren't going to cut it. Every time you pull a lever, it cuts to an animation of the ship moving. However, this footage doesn't really help the player understand if they're making any progress. Because watching a video of this section has the same problem, looking at online tutorials won't help.
Now, there is no question Grim Fandango has tougher puzzles. (Still don't understand how the developers expected us to figure out that Peanuts Rocket Fuel caper by ourselves.) Even though there are trickier sections, they shouldn't give you much trouble after looking at a walkthrough.
However, outside help won't help you with the anchor scenario. More often than not, players will solve this riddle, without understanding why.