- Anti-Climax Boss: The Sphinx. She is outright harmless if you know what to do, and narrowly avoids being Zero-Effort Boss because she is a threat if you don't.
- Breather Boss: The Blue and Silver Knights. Basically the Red Knight but stronger and no new moves. The player is also stronger when they reach them, and since the game is unforgiving, at these points the players have adapted, unlike the bosses.
- Catharsis Factor: The Grim Reaper was a pain in the neck in the original game, making the time limit even more unbearable. Here he is not just beatable, he is also a very weak first boss.
- Growing the Beard: The original Wonder Boy is still considered a solid game, but Monster Land's introduction of it's fantasy setting and RPG elements really helped the series stand out from the crowd as something fresh and unique, setting the foundations for future Wonder Boy games.
- Porting Disaster: The Amiga version had stumpy graphics and tinny sound, did not label shop doors, and had a small play area to fit the status border. (The Master System version instead compressed the HUD into a small bar and put the rest of the info in a pause menu, resulting in a much more playable screen size.)
- Scrappy Mechanic: The time limit is inoffensive for the majority of the game, if a bit suffocating at times, but becomes a nightmare by the final stage as in that level it no longer resets when you enter a new room like it previously did, requiring you to go through the longest and most confusing stage in the entire game (final boss included) without resetting the timer once. It's the only stage that's actually physically impossible to complete without taking some damage due to the timer running out, and if it's your first visit to the level and you don't know the very specific route required it will be the death of you.
- That One Boss: The Ghost/Hobgoblin. It fights like the Knights, except it has a devastating and very hard to avoid beam. Which is unblockable. Unless you have the Legendary Sword, hidden in this boss' level, good luck trying to beat this guy.
- Wake-Up Call Boss: The Grim Reaper is pathetic and easily perfected. So is the Vampire Lord, whose fireballs can be blocked by a shield and he can be tricked into doing a very easy to counter charge. But then we get to the big Mucoid, who jumps around and sometimes avoids the player, and will not stop spawning minions. It's the first creature that is actively dangerous to the player.
YMMV / Wonder Boy in Monster Land