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Interesting Encounters

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How do you make your "boss" or end-of-dungeon encounters challenging and interesting beyond "they hit harder than usual"? I'm thinking of things like figuring out specific weak points, having to use flavored skill checks, and generally having to think outside the box.

Pic related, threw a magically enraged one of these suckers at a lower-level party, strikes did extra damage but had a chance to hit (and shatter) adjacent tiles, creating areas of rough terrain. Simple, but made my players think about how to approach it beyond "hit it until it's dead".
I think using 'vidya' effects like this are an effective way to make boss fights more interesting.
Make them fine some random object that they dont know much about and that they will think is junk, barring like a nat 20 arcana check. And then it turns out there's some machine that's missing a piece, and that's the piece, and it's the only way to kill the guy or it weakens the boss.
Other examples of vidya effects?
If they think it's junk they won't take it with them. PC's care for very little that isn't money or obviously useful most of the time unless you're playing to a specific PC's interests.

I tend to give my bosses Classes, regardless of their Creature Type.

This means they don't just get the typical Feat at every Odd Level, but also get Class Abilities.

You wanna challenge a party? Do that.
Collapsing buildings, adds terrain plus a serious time pressure element.
Reinforcements, you have to win soon or else you'll be overrun.
Stop X before he does Y, where X is some miniboss and Y is something that makes the battle more difficult without just adding health or whatever.
Shifting battlefields- bubbling lava pools, clockwork gears, giant sandlions, spiders shooting webs.
Combined arms tactics; you have to get past the miniboss somehow or the archers will fill you full of arrows.
Limited time- take too long and you'll lose the objective, the boss itself doesn't matter.
Changing boss- this one's hard to do in a lot of tabletops without it seeming gamey, but having the boss switch tactics halfway through (it's losing, after all) and change the party's focus.

Really, you can take any vidya you like and there's probably an example or two. The main idea is that every round should play out differently. Think of your boss not as a pile of health that deals X damage every round, but as a piece of a puzzle. There should be too many things that need to be done and too little time.
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>try to do this with enemies
>player starts yelling at me because it's class features and says no one else should have them
>says he gives up because "he's already dead"
>he's the one who decided to fuck with a large group of actually non hostile NPCs
I hate it when a player complains really loudly about everything and it's his fault it's happening
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I'm GMing a Final Fantasy campaign at the moment, so dramatic boss fights are par for the course. Since making vidya-style bosses is not only encouraged, but an active part of the system itself (25 pages dedicated to creating enemies alone), I tend to spend a lot of time on my boss battles to make them interesting beyond "here's a big dude with two million hit points, have fun" (although there's admittedly been a few of those as filler bosses).

Most of the bosses I design tend to have some sort of gimmick to make the fight harder and more complex than normal battles in some fashion, whether it's constricting webs that make it harder to move around or the boss absorbing power from magic crystals in the immediate vincinity. Boss fights should have different rules in place than normal fights, otherwise you might as well just have thrown normal monsters at the party and doubled their hit points. Be careful not to make your gimmick too complex though; The gimmick should serve to make the fight more interesting, not to overshadow the fight itself.

Most of the time there's also some sort of weakness in place that can be used to counteract this gimmick (burning the web, destroyed the crystals etc.) which may or may not be tailored to the party. If you have someone in the party who's been standing on the sidelines a lot, a good boss fight designed around their abilities can serve to make them feel more important. Otherwise, just make them reconsider their tactical priorities a bit. Every turn a character spends destroying crystals in the background is a turn they're not spending to prevent the boss from going ham on the rest of the party, but they can't just ignore them either.

Alternatively, you can also reverse this; The boss has a weakness which, if exploited, can make it laughably easy, but there's a mechanic in place that prevents you from just exploiting it outright, and you'll have to find a way around it first.

The most important part to remember when designing a boss battle, however is making it memorable. This can be done through other ways rather than just making it strategically interesting; Throwing down with the BBEG is almost always going to be memorable if you're playing your cards right, for example. Also make sure you don't stick purely to formula either; The above points are good starting point, but it's not something you should be following blindly all the time either.

Some of the more interesting bosses the party has fought so far:

*An Antlion, which counterattacks for huge amounts of damage when hit with physical attacks. However, being hit with Water damage also blinds it, meaning those counterattacks have a good chance to miss.

*A giant spider lady who uses her webs to constrict the party. However, the webs can be burnt away with fire damage to free the party, and she's also weak to fire magic in general. This gimmick never came into play. ;_;

*A giant magical tank with a cannon that hits for outrageous amount of damage after a moderate charge period. However, being hit with lightning damage causes the tank (and the charging process) to grind to a halt. This is further complicated when the crystal array on top erects a lightning shield mid-fight which lasts until it's destroyed. And there's also two turret cannons to contend with.
I had a player complain once because he got arrested in a town, and he wanted to go ahead and go home because "he wasn't doing anything." Despite the fact he's constantly going into the other room with the GM because he runs off to do shit by himself in towns, and leaves the rest of us sitting around in the game room waiting on him.
I have a player who always wanted to have downtime even in the face of something really bad going to happen if they left the BBEG to do it's thing. Then complains when the BBEG gets more powerful because he let it get more powerful.
Did you show him the section in the DMG where it explicitly gives rules for adding class levels to monsters?
I made my players fight a bard who could endlessly summon rats, all they had to do was stop him from playing his pan flute. They died because they would rather swing swords at swarms.
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This guy lost an arm after a barbarian crit. He enraged, broke the halberd with his foot (transforming it in an axe) and then proceeded to nearly wipe the party.

On the second encounter, he threw his head at the aforementioned barbarian on sight, knocking him off. Then he started whirling around (couldn't see shit).

The only reward was the cranium, which the barbarian used for almost half campaign before killing the party's mage when he was asleep, because the skeleton head was telling him to do that all along

Not bad for a low level dungeon boss I suppose
>plan a unique encounter for the end of a dungeon
>foreshadow it throughout the session, even give hints as to what the gimmick is going to be
>party ignores everything and goes with the "whack it 'til it dies" strategy
>get mad when it doesn't work and a character dies because of it

There's still rumors flying in my FLGS that I'm a bad GM because the barbarian drowned in an otherwise easy encounter.
Forgot to say, obviously the barbarian used the cranium as a helmet, because muh savagery
My most memorable boss fight was a Skinwalker. He wasn't strong, but he was there to divert the party while the demons showed up. And divide them he did.

He could change his shape as an immediate action to look like someone else, with a +25 to disguise. He could also mimic voices, albeit horribly, so it sounded like party members or liked NPCs were in trouble. If you touched him while he was disguised, it was a DC15 Will save or be stunned for a round.
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>Make thread, gets no replies
>"Aw well"
>Stop following thread for a day, assume it gets deleted
>Come back to this by chance

This is great stuff!

I'm absolutely going to modify and use the mechanic for the antlion, I'm actually planning on using them already (PCs are in a huge desert).
No-pressure downtime is fun.
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