Sidekick builds - any fun ideas?

[Darth Credence]

My players really like the idea of sidekicks, so I am creating several that can be a possible help to them. I'll post the ones I'm doing, and if anyone has any fun ideas, I'd love to hear them.

First is Sancho. He is a changeling as his base, with the expert class. He is mostly designed as a spy - Sancho is very over the top and distracting, as is designed as kind of a buffoon that people will dismiss. He has four other well defined personalities that he will switch to to do his actually spying and information gathering, and can of course change to different looks when necessary. My favorite of the other personalities is the old man who hangs out at the bar gossiping with people.

Next up, although the party passed him by so he won't be used, is Viribus. His base is an ape, specifically a gorilla, with the warrior sidekick class. He was held captive by a witch and wizard who were experimenting with him to try and teach him to talk. Had the players rescued him, he would have followed them as a sidekick. Instead, they didn't do anything with him, but they did convince the witch and wizard to rekindle their love. While this was a bad idea in some ways, because these are not inherently good people, it did change their outlook on things. They may meet up with them, and Viribus, again, although by the time that happens Viribus will no longer be caged, he will likely be their butler, communicating by sign language.

Finally, I have Akogi. She is a slightly buffed eagle - one of my Deities uses an eagle for a symbol, and has been sending an eagle to give guidance to the Paladin of the group, so this eagle has been touched by the Deity. This resulted in the damage done by her talons to be on par with what the giant owl does, and increased her charisma. She is a Caster class, focusing on healing. I'm going for a theme with it, where it is acting as an instrument of the Deity's will so it will have helping spells, and otherwise something that I think can be flavored for a bird easily. Cantrips are Guidance, Sacred Flame, and Thunderclap - the first two as divine energy, while the third is from magically increasing the force of its wings beating. Shield of Faith, Healing Word, and Cure Wounds are her first level spells, with Aid and Gust of Wind as second level. Four of those are the divine power coming through, while Gust of Wind would be her wings flapping with enough power to create the wind. She is herself a holy symbol of the Deity, so she has a focus for the material component.

I don't know that any of them will be regular fixtures of the game, as opposed to temporary things that join them for a mission or two. They only planned on having Sancho around for one scouting mission, but he proved his worth in the most recent session, so they might not want to let him go. He and a PC snuck around behind a group that was trying to ambush them, while the rest of the party strolled towards them. They both had great rolls for sneaking, and as the rest of the party closed in, they launched sneak attacks from behind. They killed one ogrillon before it knew what hit it, and had a second on the verge of death during the surprise round. They both had high initiative, too, so at the start of the next round, they finished off the one from the first and killed another one, eliminating half the threat before anyone else got to go. This might be too much help for the group, as they are already fairly competent, but they will need it for this mission because of the sheer numbers attacking them. Akogi, meanwhile, will likely only step in when the paladin specifically needs help or guidance. He happens to be afflicted with mummy rot right now, is down to 5 hp, and has to make it to a town a full days travel away to find someone who can remove the curse. It looks like he is going to go alone and rejoin the group once cured, so Akogi is going to join him and help him through.

[MrCharlie]

I'll answer this in two ways-first, what an optimial sidekick looks like, and second how I would actually approach design (because optimal sidekicks aren't always fun for the party).

So with sidekicks there are several potentially powerful options. In general, the warrior or expert class is best positioning to make use of a monsters natural stats, while casters tend to be best as monsters with good mental stats

Ironically, the design of the sidekick class incentivizes giving the sidekick a base array that gives it things that its classes don't. For instance an expert should have multiattack and weapon proficiencies, while a warrior might be served by skills such as stealth, a bonus action hide ability, and one singular powerful attack. Hence the best warriors would make good experts from their starting blocks and the best experts make good warriors from their starting blocks. The exception is when an expert or warrior can double down on something.

For instance, shadows, skulks, and darklings are all excellent warriors. Each of them have a single, super strong attack that either does a boatload of damage or inflicts a really brutal rider effect. Hit with a shadows main attack three times and you've just taken 3d4 strength damage, which can be a straight up death sentence. Combined with ability score improvements, great stealth, and immunities+resistences, shadows are kinduve super strong warrior sidekicks. Skulks and darklings get an inherent sneak attack effect (requiring advantage) that can trigger multiple times, so you can deal ~3d6 damage every attack. Sulks also get invisibility and built in stealth expertise, and darklings just have amazing skills.

Cockatrices are also pretty nuts if we assume their petrification DC is DEX based and then simply get their DEX to 20. Petrification is a bad effect to be hit by, even if it eventually ends.

Animals such as crocodiles, wolves, and warhorses/giant goats are also quite strong for similar reasons-once they start attacking multiple times with their strong attacks they do great things. A crocodile grappler might even have some mild build support, if you take enough feats.

It's also worth noting that warriors get armor proficiency, so animals at least can wear barding if that was in question. Some humanoids also make decent warriors simply because they have good stats and can be discount champions or barbarians, like the Thug, Scout, Gnoll, and Lizardfolk. The Satyr is also decent because of magic resistance.

On the other hand experts tend to be NPCs like Skulks, Thugs, Darklings, Scouts, and even Lizardfolk, as they all get multi-attack or a strong enough attack to make up for it, and at least some skills or a useful non-skill bonus. As an expert you also want proficiency in armor and weapons so you can get the tools and simple weapon proficiencies, so you are generally some type of humanoid or tool or weapon user.

Some other interesting choices include Tridones (a type of Modron) which has truesight and at least mediocre stats, as well as a bunch of attacks, and oddly enough mounts whom gain a bunch of abilities which help their riders and increase their survivability and mobility.

For spellcasters: The answer is the pixie. The list of monsters which even qualify is low-and most of the optimal ones are humanoids. Or pixies. I'm serious here, pixies are overpowered. Some fascinating options other than those boring ones include the Blink Dog (Blink dog is a language, look it up), Giant Owl (ditto), and the memphits (pretty terrible in the role but valid).

Now, onto philosophy.

In general, I would only add in an optimal NPC is a player is controlling them. This may seem a bit odd-why would a player control a sidekick? But there are a few good reasons for it.

A. For some reason it makes sense in story.
B. For some reason they want a less complex character.
C. For some reason they want to play a really, really odd race, like an animal or a spirit.

In those circumstance, I'd consider doing something like busting out one of the weirder warriors, or giving them a pixie spellcaster or darkling expert. In each case they are, more or less, discount main classes that get some fascinating special powers to make up for it. There are a few, like a skulk warrior, that are really strong too.

There are also some circumstances where I might, for instance, give players control of their own reanimated character, like if someone uses create or control undead on a murdered party member when things get a bit PvP. I would have done this at least one time in memory-and in that instance I'd have given them the ungodly horror that is a Warrior Shadow. In fact, some of these, such as the Warrior Shadow, make a strong case for being stronger than a lot of characters, albeit hyper focused.

Oh-and option D. They lack a role. I took this option myself-I made my players a scout expert and now they have someone with all the skills they lack so they can roll an odd thieves tools, sleight of hand, or survival check. Before that they had a warrior thug whose existence was centered around acting as a meat shield for a wizard heavy party so that some of them might survive (and he was promptly dropped once a few of the died and re-rolled).

But outside of that? I'd go with interesting sidekicks.

For instance, I've bent the rules a little and given one of my players a sidekick Imp. The long and short of it is that this Imp ended up becoming a major memory of the party, and they managed to flip it's alignment 180 with one of the alignment effects that does that. For this reason, glubsnout the Imp because Slubgnout the spellcasting sidekick. Because of the campaign, party, and roleplaying, it made sense to turn the familiar into a full party member.

A good type of character for this are pets, mounts, and other animals whom the players are invested in. In those circumstances, you might make them a full sidekick.

The final example is if you want to make something weird or really cool, something like a blink dog or flumph spellcaster, a warrior skulk or a darkling expert. It would be a fascinating way to explore, well, the exploration pillar-and give the party a powerful ally to play with as a reward for them going out and interacting with the world and the fantastical aspects of it. Also, building sidekicks is fun.

[Darth Credence]

As you can probably tell by my choices thus far, I'm not really interested in creating optimized side kicks. I'm much more looking for interesting ones that fit into the story somehow. Sancho I had because I like him, and the players were being sent on a mission and asked for a scout to help. The people sending them were relieved for an opportunity to get Sancho out of their hair for a while. The other two fit the story quite well, so I made them.

I like the ideas at the end of some interesting types. I'm going to do a dive of skulks tonight and see what I can get out of that.

[The Cats]

My game has 4 players and it's pretty often that one can't make it for a session so instead of me having to rebalance everything around 3 characters, letting it ride and making 3 PCs go through challenges meant for 4, or cancelling the session, we're instituting a sidekick strategy.

Every PC has a sidekick that is a creature that has a plausible reason to pop in and out of existence. Whenever one player can't make it, one of those present will just bring his sidekick in so the groups power level doesn't dip as drastically.

The wizard has a Slaad tadpole (that can talk and has slightly better stats) names XinXan who appears when she tries to cast a spell through her Chaospire(tm) staff but it backfires. He can only remain on the materiel plane under her control for a short time before getting sucked back into limbo.

The bard has a satyr named Tem-Yon who is actually an archfey she recently freed from being imprisoned within her cil shawm. He's just messing around when he shows up so not going to bother using any real power, and he takes off whenever he gets bored.

The monk and cleric haven't actually put their's together yet but some possibilities are the monk's bonsai inhabited by a nature spirit animating; the cleric's god sending a divine servitor; the monk's spectral tiger (way of the astral self re-flavored) becoming a little more physical; the cleric summoning a runeslave (he recently underwent a ritual to become the Lord of Wrath to save the world from an army of giants. long story. Runelords are involved.)

[Kane0]

Due to real life i’ve made it a policy to have a sidekick version of each PC, so if somone can’t make it someone else can use the sidekick version of the missing player for the session.

If i had a situation where the group was permanently smaller I would start putting in some interesting creature minions, but I know for a fact they will use them as expendable trap-springers/leeroy scouts so will need to compensate for that. Maybe something weightless or blind...

[jojosskul]

The one sidekick my players have so far is a single bandit named Ted because they took him prisoner when I wasn't expecting it and I had to make up a name on the fly. His fellow bandit Steve wasn't as lucky.

Ted became a party favorite and he honestly didn't really like working for the mysterious figure who sent him to retrieve an item the party had already found in the first place. So,with the promise of protection from his former employer, he became the party sidekick.

Then Ted found out, by becoming an expert, that he has a knack for buying/selling magic items. Ted no longer travels with the party, but through ASIs/Persuasion expertise he gets to live the wealthy lifestyle and serves as the party's magic item broker through the Xanathar's downtime activities.

I now plan to make this random bandit's magic item business take off and use him as the slow drip magic item source in all my future campaigns. Ted's Terrific Treasures has a nice ring to it. As long as the party can keep his former employer away from him anyway...