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  • Most bosses in No More Heroes can be hard before you learn their attack pattern.
    • The Rank 8 boss, Shinobu, has a large array of hard to avoid attacks, dodges most attacks, and when she gets low on health picks up an attack that drains nearly all of Travis' HP, so much to the point that anyone would mistake it for a One-Hit Kill attack, as well as a Spam Attack version of her Sonic Sword attack. Confounding everything is the dark and cramped area you fight in. Shinobu, with her acrobatics, is not encumbered in the slightest. The same cannot be said for the player, unfortunately.
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    • Rank 1 Jeane is just obscene. Able to counter every attempt at a grab and dodge most incoming attacks as a matter of course, while doing major difficult to dodge damage. This boss is so fast that it'll Flash Step constantly in order to blindside you, and as the fight goes on, the arena becomes smaller and smaller, making it easier for the boss to catch you in a brutal combo. The one saving grace of the battle is that the boss is a Glass Cannon, having low HP in comparison to most bosses before this one.
    • Harvey Moisewitsch Volodarskii (Rank 4) and his "Travis-in-a-box" will do nicely. You can escape it by following the game's directions, but you get less time to do it every time you get put in the box, and the game seems to have trouble reading Nunchuk shakes.
    • Holly Summers, the Rank 6 assassin, is just frustrating. You fight her on a beach which quite clearly gives her a BIG home-field advantage; she took the time to riddle it with hidden pitfalls beforehand. You WILL fall in them constantly, and when you do, you will Waggle for dear life to climb out before Holly throws a grenade in to FORCE you out. And this is merely the field obstacle—Holly herself will bring you to tears by spamming a homing missile attack from her prosthetic leg. This attack is not only very damaging, it also cannot be blocked, and it cannot be interrupted. Once those missiles fly, get the hell out of dodge.. When you finally get to Holly, she'll smack you with her shovel before running away faster than Travis can run. On a beach. With a prosthetic leg. In heels. The silver lining is that Holly will stop to cover up revealed pitfalls, which leaves her vulnerable (as a bonus, re-covered pitfalls can easily be spotted with a glance).
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    • Rank 2 Bad Girl (on Bitter mode) caused some players to stop playing. From the Mooks she throws at the player (the move itself can be countered for both benefit and cathartic therapy, but you will regret it if you miss the timing), the long and damaging bat combo strings (which go Up to Eleven when she lights her bat on fire when she hits half health), or her One-Hit Kill move where she pretends to fall over and cry, whereupon a careless player who, thinking it a golden opportunity, approaches her, is thus grabbed and hitherto beaten to death. The clincher of it all is that, sometimes, she really does fall over to weep in misery and really is open to attack. Hint 
  • No More Heroes 2: Desperate Struggle:
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    • Rank 51, Skelter Helter, himself is a notable boss for not only having the ability to keep you off of him for most of the battle from gunfire to no-lag swordplay to even counter moves and fake outs which easily destroy a new player who never played the first, but he's also the freaking TRAINING BOSS and he's harder than most of the following bosses. While he may not be 100% lethal on normal, he will still hassle you more than a lot of bosses halfway through the game, and on bitter he can be a pain for a seasoned player.
    • Rank 50 Nathan Copeland combines this with a "Get Back Here!" Boss; his boombox lets him play a mean game of keep-away, with launching rockets and sonic booms. That's not the worst part; what IS is that he's got the entire room rigged to kill you, including turrents with automatic gunfire that play hell with Travis' autoblock, pinning him in place for indeterminate amounts of time and rapidly depleting his battery. Inevitably, while this is going on (during which time you can neither run nor roll out of the way) you will either take a rocket to the face or find yourself standing by one of the explosive potted plants scattered all over the room. Few things are as frustrating as hearing that little beeping sound, mashing left on the D-pad, and watching Mr. Touchdown stand there like a lump, showing off until he explodes. The "Get Back Here!" Boss comes in after your energy is depleted; making a necessary retreat to the safezone on either side of the battlefield, you recharge your weapon and rush back into the fray...only to be frozen in place again by your autoblock and have your battery drained once more. What's worse is when Nathan whips out his last trick: activating a set of 4 conveyer belts with paths that lead to the center of the room. Not only does this disorient your movement (of course, Nathan has no problem getting around it), but the beginnings of these conveyers are primarily where you find those explosive potted plants, which leads to 4 of them getting grouped up, meaning, should he feel like it, Nathan can detonate a big ass explosion that deals a TON of damage if not outright kill. This completely renders the center of the room a danger zone, which, of course, Mr. Copeland loves to stay at.
    • The Rank 24 fight against Matt Helms. You're in a small room, there's almost no places to dodge, his attacks are not well telegraphed like any of the other bosses, and he's got a bad habit of just sitting around throwing difficult-to-dodge Molotov cocktails that break dodge patterns and set you up for massive hits. He's invincible during the whole move, by the way, and the Molotovs leave small fires behind that can also mess you up. If you're fond of dodging in his face all the time, you'll find he likes throwing his axe smash attack at different speeds in order to throw you off and nail you. Throw on a crapton of health to make it last a while. The good thing is that the cramped arena becomes a non-issue as your duel indiscriminately sweeps the floor clean.
    • The Rank 8 Fight against New Destroyman. The first dual boss of the game, and while only one stays on the ground for most of it, the other will snipe you from the upper part of the stage if you're too far away. And you're not playing as Travis and your long range attack can't target the upper floor. On the plus side, it becomes surprisingly easy once the first goes down. On the flip side, "easy" does not mean "fun"—rather, it becomes tedious, as the still-active boss will spend half their time making a beeline for the beaten one to revive them. Almost certainly, the beaten one will be the melee-based boss, meaning the range-based one that likes to fly around will spend that other half of their time sniping you on places usually too far for you to do anything to them, even with your ranged attack. Therefore, once one goes down, you'll spend the entire rest of the fight camping their body to get in some free hits on the other boss when they run over.
    • Rank 7, Ryuji, has a dreadful first phase. You have to drive him off a cliff in your motorbike. A motorbike that can't even make a turn without falling off the cliff. Also, your opponent has a much better control of his bike, and he can push you easily, while you have to get him while he's not charged (he's invincible when charging, and just touching him will send Travis reeling away). The best way to win this is to escape Ryuuji's attack without killing yourself in the process, and wait till Ryuuji kills himself! And then you get to actually fighting Ryuji, who borders on Nintendo Hard even on the easiest setting. He's way faster than Travis, has some of the fastest attacks in the game, has a move that lets him zip halfway across the arena (which he will always spam), meaning you have to work very quickly when your batteries deplete, or just switch to a different sword. He has combo attacks that don't telegraph until you're right in his face, as in too close to dodge. Then, if you've played this game through, you'll know that the second you hear the words "Come out, dragon," you're screwed. His giant energy dragon snakes around the arena, is pretty hard to dodge and will attack multiple times, and then after a few seconds, Ryuji will use his charge zip while you're running from it. If you end up having to block the dragon attack (which you will) your batteries are instantly depleted. If you end up having to take one of its attacks, it will HURT.
    • A commonly mentioned tough boss is the Rank 2 fight, Alice Twilight. She's far from impossible, it's just that she's a very subtle Mirror Boss, her attacks are pretty fast, and the worst part is that one of her attacks is specifically designed to keep you locked on the ground in Mercy Invincibility, hitting you to lock you down again the second you try to leave it. Another aspect of how hard Alice is is when she's not on her spider-limbs sword-throwing phase, she's on foot, and extremely agile. Agile enough to seem practically impossible to hit on higher difficulties (more so than any other boss in the entire series, Alice likes to spam dodge rolls like they're going out of style).
    • Jasper Batt Jr., the top-ranked assassin, doesn't look like much, but appearances can be very, very deceiving. It's not too bad until he goes One-Winged Angel and becomes a giant super powered human. The beginning of the battle seems easy, his attacks are no different than any other boss but once you knock out half of his health he stops pulling punches and goes all out on Travis. Firstly, he can teleport punch without ANY WARNING and stun Travis before hitting three more times knocking him away and maybe into one of the instant death windows if you're unlucky. Second, once you got his health down enough and you figure that it can't get any harder....guess again as he gains another attack, he will punch forward sending a blast of wind that will immediately knock Travis down regardless and send him flying back, maybe into the instant death windows in the room or maybe into the wall either way he spams this attack too and unlike the teleport punch attack this attack is near-impossible to dodge. Thirdly, the instant-death-Travis-falling-out-and-irritating-many-gamers-to-no-end windows.

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