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Cuckoo Condor itself also qualifies due to being the overall-easiest boss in the game but also guarding the overall-hardest passage in the game; its first form is borderline harmless, and its second form isn't much better.
In Wario Land 2, after completing every level and finding every goal and treasure, Wario makes his way to the "Really Final Chapter", in which he fights...the Giant Spear Man. Again.
Awesome Art: Pretty much the entirety of Shake It!/The Shake Dimension.
Also, Wario Land 4 is quite-arguably the nicest-looking Game Boy Advance game that has ever been made.
Badass Decay: In the first two games, Syrup's modus operandi was to attack Wario, rob him, blow stuff up, or some combination of all three. In Shake It!, it's to flirt with him and then steal his gold when his back is turned.
Possible Fridge Brilliance-induced justification in that attacking him head-on the first two times didn't exactly work in Syrup's favor. Using her brains and womanly wiles over brute force turned out to be a much more viable stratagem.
Breather Boss: Multiple, but Beefne from the first game counts... you just attack him and then throw him off the platform into the instant death lava.
Crazy Awesome: Wario. If he needs to get through a wood barrier, the obvious solution is for him to light himself on fire and tackle it.
Demonic Spiders: The Iwao in Wario Land 4's Fiery Caverns are the absolute toughest enemies in said game, especially in said game's Hard and Super Hard modes. They are immune to all of Wario's attacks except for his "ground pound". They attack by throwing boulders, which they summon by pounding the ground, causing the rock to erupt forth and into their hands above their heads. The Iwao use this wind-up animation as a defensive maneuver; it happens so quickly that it's quite common for them to "accidentally" strike Wario as he approaches them for an attack. Considering all of the other hazards that the level in question features, the damage from said rocks can easily stack up rather quickly if players aren't careful.
The Pouncers from the first game are essentially knock-off Thowmps with the added nastiness of being able to kill Wario instantly even if he's full size not only if they crush him but also if he so dare touches their spiky sides. They also have horrible hit boxes as touching a mere pixel of their spikes counts as death! Some levels require you to stand on their tops which is the only safe spot while dodging enemies where its very easy to accidentally walk a bit too far off their sides and step on their spiked corners.
Difficulty Spike: Wario Land 4's Super Hard Mode is definitely one of these when compared to its Hard Mode, especially when it comes to time limits.
Many people found the on-fire theme in Wario Land 3 to be stuck in their heads for years.
Not to mention the music box theme from the same game, especially the version that plays during the ending credits. This troper hasn't played the game in ten years, and I still can hum that song note for note.
"Hurry Up!/Countdown" from Wario Land 4 is this, full stop. Guaranteed to induce a sense of urgency in any situation. Use it for your alarm, and never sleep in again.
It was also because she was the first female Big Bad in a Mario universe game. (Yes, she predated Cackletta, the Shadow Queen, the Golden Diva, etc. by several years.)
Wario himself was one in Super Mario Land 2, which is what led to the birth of this series.
Excuse Plot: The story in every game in the series can be summed up as Wario trying to get as much money and treasure as possible while defeating any enemy creature that happens to get in the way.
Fanon: The games have never given Captain Syrup's first name, but everyone assumes it's Maple. It does have Word of Dante on its side, though, having been used in a Famitsu article.
First Installment Wins: Look at the page image! Super Mario Land 3 is the most popular game in the series.
Game Breaker: In the original Wario Land, the Jet Helmet allowed Wario to fly a certain distance by pressing B in mid-air. Wario keeps flying for a fixed distance (at which point it will fly downwards like landing) or until the player presses B again. But, double-tapping the B button caused Wario to stop its current flight and start a new one while still airborne, allowing him to fly as far as pleased.
The Debug mode from the first game (pause the game and press select 16 times) is much worse, as it allow you to manipulate which Wario you have and your number of lives, coins, hearts and even the amount of time you have.
Needs More Love: This series is sadly underappreciated, especially with Wario Land II and Wario Land 3, which some consider some of the best platformers ever devised. It's largely ignored in favor of Wario Ware, to the point of even being shafted out of Super Smash Bros.. Brawl representation. Still, Wario Land: Shake It! was pretty successful.
Some of the enemies in Wario Land 4 are pretty disturbing too. In particular, several enemies in Mystic Lake tend to have huge fangs suddenly appear on their mouths as they try to bite you. Especially that one that pops out of holes in the background. Dear God, that thing is freaky...
Sequel Difficulty Drop: To say the least, getting 100% completion is much easier in Wario Land 4 than it was in Wario Land 3.
Also, Wario Land 2, 3, and 4 are all one of these when compared to Wario Land 1 (especially 2 and 3, in which you literally CANNOT die outside of 3's Final Boss fight).
The first boss in the original game probably counts.
So does Bloomsday/Scumflower in Shake It!
Just Bloomsday? Try every boss from Shake It!, with the exception of Rollerantl.
Hot Roderick is a good example of why one should not play tennis while in a High Speed Battle,
Chortlebot is a Monster Clown who happens to be airborne while you are not, resulting in a harrowing pseudo-Colossus Climb with him raining down attacks all the while,
The aforementioned Bloomsday is a floral sumo wrestler with an annoying ability to stir hurricanes,
Large Fry is the ultimate Flunky Boss, creating so many enemies that you're too busy fighting them to see his Macross Missile Massacre incoming,
And finally, we have the Shake King. His first phase isn't so hard, but his second one gives you a good idea of what Touhou would be like on foot.
To bring that point home, the Shake King's electric ball attack during his second phase combined with some of his other attacks turn the boss battle into a Luck-Based Mission depending on where and how they bounce, and if you die on the second phase, you get sent all the way back to the first phase. Hope you have enough coins for some recovery potions.
Monsoon Jungle on Super Hard difficulty in the same game.
Pinball Zone on Super Hard difficulty in the same game (mostly due to how ridiculously short its escape timer becomes).
Hotel Horror (from the same game) starts out as one of these on Super Hard Mode due to its first room becoming utterly loaded with Menonos that all become able to very-easily One Hit KO Wario.
Also probably the first boss level in the original Wario Land, partly due to having the most annoying boss in the game, aka the one for this series under That One Boss and "Wake-Up Call" Boss.
Uncanny Valley: Many, many bosses. Indeed, the clown bosses in the series hit the lowest point without even trying, with Rudy looking creepy, Clown-a-round looking really, really artificial and Chortlebot looking somewhat demonic. But then you've got the other bosses, like most in Wario World. The Winter Windster is disturbing. The Mean Emcee is disturbing. Brawl Doll... dear God it's disturbing looking like a plastic cupid doll with overly large eyes, and that's before it turns its head 180 degrees round while laughing. They probably look worse than characters from the Polar Express.
Unfortunate Implications: Wario Land 4 has you go into a variety of interesting, creative worlds... to set off a bomb which DESTROYS THEM COMPLETELY. Every single level.
They apparently get better, as you can reenter them as many times as you want. But it's a moot point, as the entire pyramid collapses at the end of the game.
Visual Effects of Awesome: The hand-drawn sprites in Wario Land: Shake It!/The Shake Dimension look very nice.