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  • 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.
  • Anti-Frustration Features: If the time runs out, you won't be instantly killed, you will only take a heart of damage. Since the time limit is tight, this is a lifesaver.
  • 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, the Death Master 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.
  • Nintendo Hard: Within the Sega Master System version, the bosses can be killed in just a few hits each, but you only have one life, unless you gain more lives through score (and continuing is impossible). Wherein the Arcade version, the bosses are much much more difficult; but by adding credits if necessary, you can continue playing should you die (up until you reach the final stage)… take your pick.
  • 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.
    • This becomes even worse when combined with the sudden permadeath in the last level. So, you might have spent a lot of coins to get through the game, die because of the tight time limit to the final boss and have to start the game over. If you go to the final battle with one heart, you can't win the game.
  • That One Boss:
    • The Ghost and Hob Goblin. They fight like the Knights, except they have a devastating and very hard to avoid beam. Which is unblockable. Unless you have the Sword of Legend, hidden in this boss' level, good luck trying to beat this guy.
    • The Dragon. The Final Boss is by far the toughest challenge in the entire game, and everything else is to prepare you for his fight. He is only vulnerable in the head, so you have to jump to land hits. It's hard to land more than one attack before he retaliates with his hard to avoid fiery breath. He has a ton of hitpoints, so the time limit WILL run out at least once, meaning you will take damage. But worst of all, you only have one chance to beat him, or you have to start all the game over.
  • Wake-Up Call Boss: The Death Master 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, meaning that you can beat him while standing still if you have bought a shield. But then we get to the Myconid Master, 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.

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