Every heroic adventuring party eventually meets THAT NPC, the one who stumbles into the adventure, wreaks havoc, and somehow becomes the group’s most loved emotional support buddy. Maybe they’re clumsy, maybe they’re cursed, or maybe they just talk WAY too much, but for some reason, you can’t bear to let them go. These aren’t just sidekicks… they’re walking plot twists, chaotic mascots, and occasionally the reason your DM has to rewrite the entire campaign. Here are ten sidekicks so endearing, so ridiculous, and so utterly adorable (except Mort) that your party will risk everything just to keep them around.

All of this amazing art in this article was created solely by Yuma Hamasaki. You can find her incredible talents on Bluesky, Instagram, or her Twitch account!

Twiggy, The (Former) Alchemist’s Apprentice

Twiggy was once an Alchemist’s Apprentice, that is until mixed up the ingredients “eye of bat” with “eye of cat.” The Alchemist was less than pleased to find that his beloved cat was missing an eye.

Now unemployed, he’s looking for work, possibly with an up and coming adventuring party?

Be careful though, his potions can be quite…unpredictable; healing potions that heal but cause blindness, invisibility that only last 6 seconds, sometimes even mislabels his potions when he’s in a hurry. Make sure you double check your poisons and your healing drafts!

Teddy, The Animated Stuffed Animal

This well loved Teddy Bear spent its entire life in the room of the daughter of a wizard. After a wayward spell from the young daughter, the stuffed bear came to life! Its sudden sentience frightened the young wizard in training and she quickly threw it out the tower window. Lost and confused, Teddy attempts to find meaning in its life. He’s often helpless, clumsy and a bit naive with this new world.

Will your adventuring party adopt this cuddle buddy?

Pickles, The “Help”

Pickles was originally hired as “The Help” for the fighter guild. He was assigned to every menial task you could imagine. Unfortunately, he’s a bundle of nerves, which causes him to mess up or misinterpret just about every task he’s given. Pickles has been known to polish swords with acid, mop the floor with beer, made and served lunch that consisted of whatever he could find outside such as grass, poisonous berries, and whatever stuff he found local animals eating. Now he’s been fired after giving the guild a fit of the “Bubble Guts.”

Could your adventuring party use a new well meaning helper?

Nip, The Kobold Knight

Young Nip grew up in a large family who taught her to be afraid of everything. Unfortunately for her family, Nip was never very good at listening. All she ever wanted, was to go out and explore. To be one of those adventurers that she was constantly warned about in stories! Every chance she got, she would explore and scrounge around the local dump to find whatever she could to fill out her suit of armor. Nip currently wears a multitude of mismatched and less than sturdy armor, “fit” for any would be adventurer! Nip is more than enthusiastic about her future, if only her body could match her upbeat mood, as she is as clumsy as she is optimistic.

Could your adventuring party use one more knight in its ranks? Nip is ready when you are!

“Mama”

Mama is just your average, run of the mill, overprotective mom. Or so she says… Unbeknownst to many, she was a former gang leader back in the day before she settled down for the slow life. Now that her husband has passed on and her kids have flown the coup, Mama is feeling restless. She’s mean and absolutely terrifying to anyone that even looks are her “little babies” the wrong way.

Could your adventuring party use a mom that not only cooks and cleans but can also take out the “trash” when need be?

Guy, The Mailman

Guy was just supposed to deliver the mail to the intrepid up and coming heroes, but then he just kept following them around. And the worst part of it is, HE. JUST. WONT. STOP. TALKING. Facts about mushrooms, his least favorite letters to deliver, long winded childhood stories, what he ate for breakfast, long winded childhood stories about his friend Tim. He just goes on and on and on! Unfortunately for all, Guy has zero self-awareness. However, what he lacks in decorum, he makes up for in information. I guess being a Mail carrier has certain advantages…

So what do you think? Do the Cons outweigh the Pros? Would your Adventurers consider adopting this little motormouth for some juicy info?

Poppy, The Fairy With Anger Issues

Poppy is a menace to society…when she drinks. Inebriation causes her to become belligerent to even the most minor offense. Poppy has gained such notoriety that she has been banned from several villages and town’s Taverns. However, when sober, she’s as jovial and bravehearted as any other adventurer. And your in luck! Her last party parted ways with her after her last bender that caused the tavern to catch fire because “Karaoke night was a trick by Asmodeus to open a portal to the nine hells” after one terrible rendition of Highway to Hell by one local patron.

She’s a willing and able sidekick for any adventuring crew! So what if alcohol is her vice? Don’t we all act a little funny after a few drinks?

Granny Smith

Granny Smith, as she is affectionately known as, was the innkeeper for the local tavern in some small Podunk town you’ve probably never heard of. She has spent her entire life in that tiny town, forever serving strange guests, heroic adventurers, and well traveled explorers. Though she has enjoyed what she did as innkeeper, cooking and looking after her drunken “children,” with her deadly cast iron frying pan, she often laments about never being brave enough to actually go out and explore the land. Maybe it was this thought that finally broke the old Granny, but whatever it was, she suddenly became very attached to your party of young adventurers.

So how about it? Could your future heroes use someone like Granny Smith, who can cook homecooked meals, sew torn garments, heal minor wounds, and can knock an asshole out with a cast iron frying pan?

Bean, The Little Hero

Bean was born to become a hero. She embodies every intangible; She’s kind, selfless, brave, loyal, honest, and compassionate. If only she wasn’t a young child. As passionate as she is, she lacks any sort of experience that comes with being an adventuring hero, particularly when it comes to fighting. However, that wont stop her from running head first into danger!

Bean isn’t a totally useless child, she’s just…a little out of her depth. Could your party use an aspiring hero as your squire?

Mort

Mort is the embodiment of pessimism. He acts like everyday could be his last. Every menial task he does is met with a sighed, “I guess that’s all I’m good for,” or “This will all probably end in tears,” or “Four years at Wizards University…for this?” He is the tiny rain cloud on your parade, the one sour grape in your otherwise delicious fruit salad, the smelly fart that wafts about the room once your completely snuggled in bed.

Redeeming qualities? Who said anything about redeeming qualities? Do you want him or not? he’s driving all of us crazy!

If You liked what you’ve read, consider giving me all of your money.

---