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We are That Boss!
Yes we're all That Boss!
The one that you hate!
Because we are annoying!
We are That Boss!
Yes we're all That Boss!
Really frickin long
Or just breaks all the rules!
We are that Boss that you hate
We will grind you all up into paste!
One-Hit Kill moves, Tedium Personified
Or just a massive spike in difficulty!
Takes too long to show weak points!
Mission failed, you have died, won't matter how much you've tried.
We're here to show you just what it means to fight with all your might.
Not meant to be this hard, but we are, so everyone better get ready!
—Sung to the tune of Super Smash Bros. Brawl's main theme

    Video Games 
"I've been playing your game for months now! And I've already gotten you all the way up to Level 47! But that Bahamut boss is really tough. Slinky and I can't figure out how to beat him!"

"I knew the other ghosts couldn't take you. I don't even think Spooky can take you. But we'll never know that, see...'cause you won't make it past me. Especially since my machine's body is impervious to your rev-roll! I've always liked my Pac-Man...extra crispy!"
Blinky, Pac-Man World 2

"Whoa, no wonder this Brute Tigrex's so clean, it's the least hunted monster! Is it crying Tears of Joy? Wait, those tears look a lot like Armor Spheres...hmm. Odd."
Excitable A-Lister, description for the "Brand New Brute" event questnote , Monster Hunter: World

Taste the impurity of life and death
that the moon's people hate so much,
and let your first death
send you falling into hell!

In this inverted castle where everything is turned upside-down,
I'll give you a taste of the humiliation the weak have suffered!

Things you love to hate:
1. Models your lover thinks are cute
2. Athletes who are stronger than you
3. The Emperor Boss in this game

Do you wanna have a bad time? 'Cause if you take another step forward... You are REALLY not going to like what happens next.

Wait, wait, wait, I know this guy! ...Yeah, we are screwed.
Terror Mask, Splatterhouse

"CAUTION: TO PREVENT CULTURE SHOCK, DO NOT PLAY THIS SONG."
"WARNING: SHOCK HAZARD-DO NOT PLAY"
"NEVER CLEARED"

The A in "A" is the ace in trump card.
This song's concept was actually around since [beatmania IIDX] 3rd style.
The first-half begins at about half the BPM, requires the skill to sight-read complex chords, a 16-bar piano phrase with high speed drum'n'bass rhythms falling notes to play with both hands, then for the part with the scales plus scratching, one-handed skills are necessary to play the scales...... So, it was essential that I created a song using all these skills required to clear IIDX.

But at the time, the song's difficulty level was too high for the average player, so while I waited for the players' skill level to increase, the difficulty level of the gameplay slowly increased with each version, but then I saw many people easily clear charts close to the human limit at the 7th location test [beatmania IIDX 7th Style], so I was convinced that it was time to finally release this song.
I chose the name D.J.Amuro from the song title "A".
I hope each player can feel the thoughts I placed in this song.

I'm sorry to most people who haven't reached the intended difficulty level except for super advanced players, but I will be happy if clearing this song is a proof of being an elite player.
dj TAKA, song notes for the beatmania IIDX song "A" (translation from RemyWiki)

    Webcomics 
"It shoots fire from its mouth and bleeds acidic lava! Run for your pathetic lives!"
Red Mage, 8-Bit Theater #455

The End: You stand around in the open? I shoot you in the face.
Snake: AAAAAAAAA
The End: You try to hide?
Snake: I'ma tree I'ma tree I'ma tree...
The End: I shoot you in the face.
Snake: HOW
The End: You touch my parrot? Right in the face.
Snake: WHAT I DIDN'T EVEN
The End: And if I'm feeling a bit down...I say a prayer to the forest...
Snake: WHAT
The End: And THEN I shoot you in the face!
Snake: WHYYYYYYY

    Web Original 
It's a good thing Destro couldn't actually do this in the show, or the Joes' mission would be moot.

The battle with Wily's UFO is marked as the toughest in the entire series, with even the devs and playtesters confessing to be unable to defeat him... The doctor appears in the air, launching hard-hitting, homing elemental balls of death and is naturally weak to the most convoluted and difficult to fire weapon in the arsenal, the Wild Coil.

In Baten Kaitos, there are some bosses that are harder than others. Some spoken about in hushed tones, and never at night. Bosses used to scare children into submission and fill the proud with terror. And of those bosses, one stands out above all the rest.
This is the Holoholobird.
Overrated Sage

Simply defeating the enemies in each area (and not bothering with them when they eventually respawn) more than suffices to keep you at a level comparable to your opponents, which makes Tales of Vesperia feel like one of those games designed to eliminate the need to grind. Then Gattuso shows up and you realize that isn’t the case at all.
Killa Penguin, in a post about Gattuso from Tales of Vesperia

    Web Video 
"2097: the number of deaths it takes to beat the first boss! ...It's like, you're naked in school, and you have to fight 1986 Mike Tyson."
Danny Sexbang on X-Kaliber 2097, Game Grumps

"The kind of boss that once you beat you feel you really earned it, even though you may not have been all that close to losing, because you felt like you were a hair away from losing constantly. I'll say it: I respect Skeith. And fear him like I fear the Devil."

DARKNESS. (Oh my god its the Lingering Will. Time to beat you up good for the hard time you gave me in KH2!)

ProZD: Man, this Poop Dragon fight's a pain in the ass.
Anon: GIT GUD

You have to be careful with Bloat of course because obviously he's going to be doing tons of damage, [and his green champion variant] has ipecac shots. I mean, what can you say about Bloat that's good? [Beat.] Don't worry I'll wait. [Beat.] Exactly. There's nothing good about Bloat at all. [He's] super dangerous, people know the danger when you're fighting Bloat.

I've said it before and will say it again. This fight is not made for humans, you know, like my videos. We're supposed to be killing each other with rocks.
Max0r, An Incorrect Summary of ULTRAKILL Act 2 on the rematch with V2

"Minos Prime is not an easy boss. You're going to be quite familiar with all of his attacks, because he will not stop screaming them. Moves such as 'Judgement.' 'Die.' 'Thy End Is Now.' 'I Will Have Order.' These attacks will bookend your obituary, and they will do it really fucking fast. And yes, that is why the video looks bad. This game is no longer a first person shooter, it is Malenia, Blade of Michelin."

"Ultimately, V2 can be easy or he can be hard. Easy, in that he is limited by your moveset. But hard, in that he is only limited by your moveset."

"Contrary to every swashbuckling tradition you've been led to believe, standing on top of a table is actually a detriment because you can't stab a guy downward; your sword goes right over his head. And the guy on the ground can just whack ya in the shins 'til you fall down. So that's the secret if fighting these guys; is to find lower ground and beat the shit out of them. And of course, this guy seems to know this, which is why he's not getting in range of my fuckin' sword and he's PRANCING AROUND LIKE A FAIRY with his hand over his head!"

"Magaki is really baffling as a boss, I have to emphasise that. Particularly when it comes to the other bosses in this game, they are so much more complex and interesting in terms of character design. Magaki however can be summed up as an extremely cheap, horrendously defensive boss whose entire purpose is to make your life hell by spamming you and countering all of your attacks. He is absolutely no fun to fight in the slightly[sic], something which is exacerbated by the fact that his AI is perfect and can unleashed[sic] torrents of projectiles at you with ease, despite that[sic] fact that it’s difficult for a human to get the timing right for the same thing, if possibly impossible. He is an entire chore to face, and is the thorn of the otherwise pristine crown of roses."

[Another notable Timed Mission is] "That one fight against Okumura who's hatred in the Persona 5 community can only be rivaled by the passion in the Best Girl debate."
Daryl Talks Games, The Best Worst Mechanic in Gaming

"The 'turning my Stickers into Flip-Flops that do less damage, and unless I can remember what and where EACH of my Stickers are, I'm probably wasting really useful ones' is annoying, but manageable. But now I have to fight THREE of these bastards, and this can be either just another annoying roadblock or what I think might be the most unfair fight in the entire Paper Mario series, up to this point. Remember how I said that you can't pick which enemy to attack? Well, if you manage to get three matches on the Battle Spin at the beginning of the fight and get 3 Excellents on each Flip-Flop, that won't matter. But if you whiff ONE, or in my case, ALL of them, because I don't have enough practice with the Flip-Flops to know their timing, be prepared to spend a BUNCH of your time, coins AND Stickers, just to get through this fight. Each Kamek can fly SLIGHTLY upward, putting them just out of your reach, making you waste a Sticker every time. Remember, you CAN'T choose which one you're going to hit, so if you only have one attack slot and the one directly in front of you is in the air, you have two choices: waste a Sticker, or run away. It doesn't matter that the ones behind him are on the ground; if you don't have more attack slots from the Battle Spin, you. Will. Not. Hit. Him. And if you don't get rid of ALL of them, they respawn, meaning you have to go through the whole process of trying the Battle Spin, only to waste Stickers because you can't reach him. Hey Mario! Throw the fucking sandal! He's RIGHT THERE!"

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