Hardest Pokemon Bosses

The Top Ten

1 Red (Pokemon HGSS) Red (Pokemon HGSS)

I had so many problems beating him first off his Pikachu is Level 88! It WILL Kill you if you don't have a ground type. His Snorlax is very strong but he is slow. His Lapras is Immune to Hail. His Charizard can be hard without Rock type attacks. His Venusaur can use Frenzy Plant and Kill you almost instantly without Fire. And last but not least Blastoise High defenses require you to use Special attacks like thunderbolt!

The level difference is just too high and the 100% accuracy of blizzard in hail, which 3 Pokemon from his team can learn, good lord! And I thought my level 77 dragonite could carry that battle! Sigh...

The main reason I have trouble with Red is because of his levels, and moves. His Venusaur is not a problem because I have a fire type starter. Charizard, and Pikachu are also no problem Since I always use my lugia and grass type, but the main problem is that his Lapras, Snorlax, and his Blastoise have the move blizzard and all my level 70s, and 80s are weak to ice. I've never beaten red to this day he should be number 1 darn it!

His Pokémon are the highest level in ANY Pokémon game. He has Pokémon that can easily OHKO underleveled Pokémon, plus it takes tons of grinding to get to him. Definitely the hardest boss in Pokémon.

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2 Furious Master (P.B.A & Pokémon Elites)

I don't know who they are

Weirdest pokemon battle/no. 2 of the weirdest bosses in the list.

These one is...

3 Cilan (Pokemon Black and White)

Anyone who is anyone hates the monkeys. So you probably didn't bother to level up your monkey, so you have almost no chance against any of the gym leaders. Plus, the Lillipup is annoying too. So have fun...

Why is this even here. Is this some kind of joke?

WHY IS HE SO DIFFICULT

What. This gym leader is pathetic! Pidove can take care of Pansage, and your starter, A Blitzle, heck even your own Lilipup can beat his Lillipup!

4 Brock (Yellow) Brock (Yellow) Brock is a character from Pokemon and is created by game freak & Nintendo. He was the first gym leader in pewter city, and specializes in rock Pokemon . ...read more.

Only with pikachu you'll lose to him

In Pokemon yellow I remember going with the starter, pikachu and being thrashed. Nidoran and mankey, the only Pokemon who could properly beat his wretched onix only learn the correct super effective moves at later levels. They are also rare to find.

It's simple now to level up a Nidoran to level 13 and double kick him, but when I was 9 doing this that kind of grinding was nearly out of my league. 😂

5 Shadow Lugia (Pokémon XD)
6 Cynthia (Pokemon DPP)

I mean, hard! The rematch... A level 72 Lucario, a level 72 Togekiss, a level 78 Garchomp? Also, she has a well-balanced team with generally good moves (Why does Garchomp have Giga Impact? ) - bubbles1111

Weavile can't even one shot Garchomp. If anyone can manage this without Weavile, Scizor/Mamoswine combo or Altaria, you forever have my respect.

I sighed in relief when I had FINALLY beat her after the fifth or sixth time. How can she NOT be at number 2 at least? - 906389

Pushover. My mammoswine knocked out almost her entire team(I only had problems with spiritomb

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7 Mew (Pokémon Snap) Mew (Pokémon Snap) Mew is one of the fictional species of creatures from Nintendo's and Game Freak's Pokémon media franchise created by Satoshi Tajiri.

I though I beat the game until I had to catch this thing, I have that beaten the game in a year or 2!

Mew! CUTE! A LITTLE TOO CUTE!

8 Dialga (Pokemon Mystery Dungeon 2)

Dear Lord, it took weeks or even more than a month for me to finally beat Primal Dialga in Pokemon Mystery Dungeon: Explorers of Sky! - ModernSpongeBobSucks

Literally, your only hope is that he doesn't use Roar of Time instantly so that you can throw a Stun Seed or something - which is hardly helpful because he can still One-Hit KO with a single Roar of Time as soon as he recovers if your Pokémon are below Level 40.

I guarantee people, like me, bought action reply just to beat Dialga. No joke.

If you get a water starter, you're screwed

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9 Whitney (Pokemon Hgss) Whitney (Pokemon Hgss)

Whitney of all people probably was the only gym leader in all my gaming life who ever made me cry with frustration because of her Miltank which is a tank on steroids who drank super juice but her Clefairy did not cause me the least amount of trouble but when Whitney cried it was possibly the best moment of my gaming history.

Damn IT MILTANK! If you don't have any fighting moves, it is hell hard to kill because it's like a tank. It uses Milk Drink when you have its HP low enough, and Attract on your Male Pokemon. Rollout can be devastating. Really hard for an early Gym Leader.

A very hard gym leader, but not one you can't counter. Onix and geodude have no problem with this gym. I found Clair to be significantly harder.

Miltank, enough said. - PerfectImpulseX

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10 Ghetsis (BW)

The first ever time I played, I could not beat his Hydreigon. It made me stop playing for a while. - 906389

First time I fought him I had to use all my revives and max revives

His Hydreigon gives Whitney's Miltank a run for its money. Not only does that thing have a strong, balanced Special Attack moveset, but it also has full stats and is 10 levels lower than a regular Hydreigon. - Swellow

I'd say its worse than miltank because it has focus blast which will ohko almost anything that doesn't resist it because of hydreigon's high special attack stat

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The Contenders

11 Angeallen (Pokemon Platinum)
12 Ultra Necrozma (USUM)

Higher stats than Arceus, Totem aura, and excellent type coverage. How much more OP can you get? - Darth_Tyrant

Hardest than anything on this list by far

It wasn't THAT hard...at least, to me anyways. - PerfectImpulseX

True, it's easy to bet if you know what you'll be fighting and make up a strategy, but if you're going in blindly or in a challenge run (like a nuzlocke for example) this thing is a dream wrecker.

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13 Lance (Pokemon HgSs)

He has over powered pokemon and too many items! Even with my supply of over 100 full restores I still managed to never ever ever beat him so a can't put Kanto bosses on here. The only reason he's #4 is because I thought that other people could beat him more easily than the Top 3! In fact the only other one I flat out couldn't beat was #1 who can beat you way faster!

You have to go through the elite 4 with battered Pokemon and then you have to beat a guy who's strength is the 4 put together!

All those Dragonite with hyper beam -.-

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14 Primal Dialga (Pokemon Mystery Dungeon2)

It will let you approach it unlike normal Dialga but it can easily K.O. You or your partner in 2 hits and has about 670-1000 HP!

Isn't this already on the list? - ModernSpongeBobSucks

15 Steven Stone (Emerald)

If it hadn't been for my Blaziken dodging Metagross's Hyper Beam, I would've been destroyed.

How is this only number 15? My legendaries were knocked out with EASE by this guy!

2nd hardest leader ever! (cynthia took a level 100 tortera and 50 full revives) - Wisecrack3

Such a nightmare. Aggron can beat my level 98 deoxys in 1 hit in defense form.
Metagross beat my level 100 mega rayquaza.

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16 Duksnoir and 7 Sableye (Mystery Dungeon 2)

3 against 8 gives the enemy a 5 man upper hand! The sableye have about 93 Hp but dusknoir may well have about 800 Hp! Dusknoir can deliver about 70 damage per blow and Sableye can can do about 30 do the math and that's about 93 damage per team member, ouch! However these are fron the math is best their strongest attacks and if they all attack so don't get too worried!

I hate fighting them it's so hard and there's so many sableye. Plus it takes forever to take down Dusknoir. - TheStupidHobo

I beat dusknoir on my first try. He was EASY! If you thought he was hard, wait until you meat primal Dialga. PD will murder you

This is like Luxray and the Luxio times a bazillion. Your only strategy is to confuse Dusknoir. For every 1 battle I have with Primal Dialga, I have 10 battles with these guys.

17 Cynthia (Pokemon B/W)

I haven't played this, but from what I've heard, Cynthia is a beast.

Her garchomp is the most terrifying pokemon ever... even for an experienced player, if you don't have a strong ice or dragon type you are screwed. And that's without having to worry about the other pokemon...

THIS is what you think the hardest is? Just use whoever you used to beat Ghetis with! - Pikachulover1

If you have a hydriegon that's the same level as her pokemon the only thing you have to worry about is garchomp (i was a cheap person and used the volcarona stratagy) but you want fire blast for lucario and roserade, draco meteor to either 2 hit or ohko the togekiss, dragon pulse deals with garchomp, and outrage can also deal with milotic as long as it doesn't go for ice beam you should be able to ohko or 2 hit most of cynthias team and spiritomb just draco meteor and then outrage.

18 Evice (Colosseum)

He has lots of powerful Pokemon such as Slaking which gets skill swapped. He has a Salamence and tons of other powerhouses such as Machamp and Scizor. At least the Shadow Tyranitar you have the Master Ball but then again you might of used it on Shadow Metagross.

Seriously, extremely high level pokemon, with slowking skill swap on slaking and shadow tyranitar. Htis guy made me lose SO many times.

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19 Lusamine (SuMo) Lusamine (SuMo) Lusamine is a fictional character introduced in Pokémon Sun and Moon. She is the head of the Aether Foundation.

Her Mother Beast form is overpowered as hell! - ModernSpongeBobSucks

The clefable is what got me every time

Strong and varied team. Mamaged to knock out even some of my overleveled mons

20 Lenora (Pokemon B/W)

After finally beating the ferocious beast known as Herdier, you have to face her Watchdog. It usually starts the battle with Retaliate, which pwns your pokes most of the time. And then it starts spamming Hypnosis and Crunch.

Had 5 tumburs I never used and released immediately after and one sawk that I used to replace my starter for the entire game, if you ask me, the first gym and second gym leaders in dpp where the hardest gym leaders, rest are easy as pie - Wisecrack3

Wow, I figured out how to beat her a long time ago.
Use your starter otherwise, but if you started with Snivy, get a Fighting type from Pinwheel Forest. Give your main killer a Chesto Berry and when she switches in to Retaliate, switch to your HM Slave. I beat her on the first try, even as a Pokémon newbie many years back!

21 Draipon (Pokemon Ranger 2)

If you chose crogunk as your partner, you are screwed. You can't get off the ship ship to change your partner, so you have to restart the game :( took me a long time, but while, but I finally got it

I had to restart my game in order to beat him because I chose Crogunk as my partner. I went back with a different partner and beat him, but was still super hard. This boss is the hardest pokemon boss I’ve ever faced myself in a game for me!

I chose croagunk. Drapion was an absolute pain! 😱��"�

22 Totem Lurantis (S/M)

This pokemon is way too broken. It has Solar Blade along with Power Herb from the start. It can immediately attack with basically a physical Solarbeam once it uses it. Not only that it has Synthesis to restore its health. Its allies also causes pain in the neck. Trumbeak with Rock Blast kills fire types and flying types, which you definitely need in order to beat. Castform uses Sunny Day, which allows 2/3 of its health to be restore and immediately charges its Solar Blade... This Pokemon should never be underestimated.

It took what seemed like an eternity just to defeat that overgrown mantis with a kimono! It's definitely the worst Totem Pokemon battle of all time. - PerfectImpulseX

This really should be at least in the top 10. - PerfectImpulseX

It's easy if U bring Salandit since he has 4X resistance 2 grass. Also easy if U have Gastly/Haunter/Gengar and U use the curse against the Lurantis and bring lots of revives and potions because it will take damage every turn. Also the Lurantis will eventually run out of synthesis meaning the curse will murder him. That's how I beat him. - POKEGAMERZ

23 Morimoto (Pokemon B/W)
24 Iris (Pokemon Black 2/White 2) Iris (Pokemon Black 2/White 2) Iris is from the Pokemon bwhite version & Pokemon black 2 & white. She ether was the gym leader in Opelucid city in white version. She first appeared to aid Bianca, Burgh, and the playable character when Bianca's Munna was stolen, & acted as a bodyguard. In Black 2 & White 2, she was the champion. Iris ...read more.

Definitely had EV trained Pokemon. She apparently had a Lapras! What the hell is wrong with that? Oh yeah! Lapras is an ice type!

Lapras for crying out loud!
She had LAPRAS!

25 Greevil (XD: Gale of Darkness)

Fighting him whilst having to catch ALL SIX of his team is a nightmare. All the Pokemon are strong. They are Rhydon, Exeggutor, Tauros, MOLTRES, ARTICUNO AND ZAPDOS. All of them also have high catch rates, especially the birds, so you will need LOTS of Pokeballs. Also, if you score a critical hit, you may accidentally KO one.

For those who are unfamiliar with, the goal of the game is to catch all the Pokemon your opponent has that are Shadow Pokemon (in Greevil's case, all 6). These Pokemon also have special attacks that deal super-effective damage to all non-Shadow Pokemon - they will hit any Pokemon you use hard with the exception of other Shadow Pokemon. I strongly recommend not purifying all your Shadow Pokemon before this match else your entire team will be KOed quickly (especially Salamence - could have not won without it! )

And if you want to use the Master Ball on them, that means no Master Ball for Shadow Lugia. And any damage you take against Lugia gets carried ...more

Speedster did a countdown on the hardest Pokemon battles and this was number 1, and let's just say he made a pretty good point. I think you should check it out and he also talks about why Whitney isn't as hard as we all say. I'm voting for this until it's number one. What are you guys even talking about for the number one choice, and in another list, Speedster also explains why the battle with Red isn't as great as we all think it is.

Have to catch 3 legendary birds, all with equal catch rates to lugia! Not only that but also 3 other difficult Pokemon to catch as well! And even if you don't catch them all their attacks are super effective.

All of his Pokémon are shadow. ALL SIX OF THEM, meaning shadow Pokémon are super effective against you (Unless you Pokémon are show too, most likely the Salamence you just caught, and to add icing to the cake, YOU HAVE TO CATCH ALL SIX OF GREEVIL'S POKÉMON, which is easier said than done. His shadow Rhydon shadow Meme (an Exeggutor) and shadow Tauros aren't too bad, but get this: HE HAS ALL THREE OF THE LEGENDARY BIRDS WITH THE EXTREMELY LOW CATCH RATES. This Guy has kicked my butt so many times. This list is rigged! Greevil should be number 1.

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26 Lysandre (X and Y)

Gyarados will give you hell every time. He's got a great theme, though.

That Mega Gyarados of his is absolute HELL to fight. Not to mention Mienshao with Fake Out. Great theme, though.

All of Lysandre Pokemon were easy with my team of Charizard, Greninja, Yveltal, Talonflame, Diggersby, and Pikachu

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27 Torterra (Pokemon) Torterra (Pokemon)

Torterra is a boss!

28 Flannery (Ruby, Sapphire and Emerald)

In ORAS, her torkoal was way too powerful, even if you're using a Pokemon that resists fire.

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29 N (Pokemon B/W)
30 Cyrus (Pokemon Platinum)

Cyrus has a lot of tricks in his team of 5 fully evolved pokemon, including heat wave on honchkrow for steel types, thunder fang on houndoom for water types and earthquake on gyarados for slower electric types. He doesn't mess around.

How is this not in the top 10? Cyrus is a killer, especially in nuzlockes with his beastly earthquake gyrados and heat wave honchkrow. I found this fight significantly harder than Cynthia, Crasher wake, and even Fantina in my most recent nuzlocke of platinum.

31 Darkrai (Pokemon Mystery Dungeon 2) Darkrai (Pokemon Mystery Dungeon 2) Darkrai is a legendary Pokemon developed by Game Freak. The only way to get this Pokemon was through two events, only one in the United States.

Okay, I agree that Dialga was REALLY hard to beat. Fortunately, I was a Mudkip and learned endeavor, so when he tried to pulverize me with Roar of Time, I used Endeavor and Turtwig delivered the final blow. But Darkrai... I made it to him two years ago and still haven't beat him. Of course I don't play the game 24/7, but still. He has a team consisting of a lot of ghost and dark types, and that really hits Cresselia hard. She's almost ALWAYS the one who faints (due to her suckish moves and type disadvantage. *Sigh*
I just need to beat him before I beat the entire game.

32 Zekrom (Pokemon Park 2) Zekrom (Pokemon Park 2)

Gave me absolute hell

33 Phoebe (Pokemon RSE)

So hard, at least on oras.

34 Champion Iris (Pokemon Black and White 2)
35 Palmer (HG/SS)

This guy is just ANNOYING! First match he has a dragonite, a rhyperior and a annoying milotic. Second match he has a heatran, regigigas and cresselia. I didn't even get there.

36 Benga (Black2/White2)

Who was this again?

He uses legendaries and pseudo-legendaries that are highleveled

37 Olympia (X and Y) Olympia (X and Y)

It took me more tries to beat her than it took me to beat the champion! But that's psychic for you.

Easy as hell couldn't find an easier battle.

X and Y may have been hard, but Olympia was the hardest of the hell known as Kalos.

Pokemon Y being my first game, and all that, I remember a little about the game.
Gym 1: 3 tries
Gym 2: 7 tries
Gym 3: 1
Gym 4: 1
Gym 5: 1
Gym 6: 1
Gym 7: 1
Gym 8: 1
E4; 14 tries
Champion: 2
Even though I was a noob I managed to beat the gym.

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38 Wally (Omega Ruby Alpha Sapphire)

All I remember of it was A PAIN IN THE BUTT.

It wasn't hard from what I remember of it. - PerfectImpulseX

Walle from ORAS has IV bred, EV training, Hidden ability Pokemon with items. In other words, it is like playing a competitive match. So hard!

39 Arceus (Pokemon Ranger Guardian Signs) Arceus (Pokemon Ranger Guardian Signs) Arceus is a legendary Pokémon from the Pókemon series. He first appeared in the 18th Pokémon movie alongside other Legendary Pokémon.

Honestly I think the reason this boss wasn't even on the list is because nobody has ever made it to it. You need to beat every temple in the past and then before you even fight arceus you need to capture every Pokemon in the temple and it's all under a VERY strict time limit. It's the only Pokemon boss I've ever fought that I've not managed to beat to this day and I doubt I ever will

ass

40 Shadow Mewtwo (Pokken Tournament)

3000 HP. A Burst Attack that will one shot you. Anything else to say?

41 Koga (HGSS)

There is one word that descibes how anoying Koga in HGSS is. Muk. It spams Minimize so you can't hit it, It Poisons you, and Has Swagger (which if you don't know, raises the opponents {Your} Pokemon's Attack and then confuses you) To make matters worse, He has this thing on the Muk called Black Sludge which works like Leftovers (gains health back at every turn) I'm suprised I had to add this as a new item, it should've already been on here, and in Number 2 after Whitney

42 General Aqua Leila (Pokemon Trozei)

It's been 3 years so far, and I still haven't beat this jerk.

43 Rampaging Entei (Pokémon Ranger)

Oh the frustration. Pokemon Ranger was one one the first Pokemon games I had as a kid and I was never able to beat it until I tried again years later.

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44 Tate/Liza (Emerlad)

Confuse Ray, Calm Mind, and Light Screen will ruin you plans. Solrock and Claydol can do serious damage. They are so hard to kill it's ridiculous, I had to slowly whittle down their health while using a huge pile of healing items.

45 Steelix (Pokemon Ranger) Steelix (Pokemon Ranger)
46 Sableye (Ruby)
47 Giovanni (X and Y)

Giovanni isn't from X and Y. He's from the original Red and Blue games I think. - RiverClanRocks

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48 The 3 Legendary Dogs (The Original Pokemon Ranger)

You have to draw more than 30 circles around them at once ( this was at a time when you had to do all he loops in one go! )

49 Maylene {Pokemon DPP} Maylene {Pokemon DPP}

If you don't have a Staravia on your team your going to get owned

50 Gardenia (Pokemon DPP) Gardenia (Pokemon DPP)

I know she's supposed to be easy but she gave me a heck of a time her roserade can own your team if you got piplup and maybe turtwig

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List Stats

600 votes
51 listings
6 years, 313 days old

Top Remixes

1. Furious Master (P.B.A & Pokémon Elites)
2. Cilan (Pokemon Black and White)
3. Brock (Yellow)
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