These are not such characters. They are the opposite of that. They are very bad at a few things and mediocre at everything else. Many of them can't even multiclass effectively, as they don't meet the attribute requirements to try to be anything else. These nerds are stuck being crappy characters until at least level 5. These characters are the opposite of optimized; they’re vandalized. Making these characters was surprisingly refreshing, after years of optimizing and trying to wring every little advantage out of a character. I recommend it to any veteran of character creation as a fun challenge and mental exercise.
These characters are made in such a way that they're bad at what they're supposed to be good at, and only mediocre at anything else. The barbarian is weak in melee combat. The wizard is bad at casting spells (and can't cast many). The would-be bard is actually a sorcerer, and is repugnant and bad at music. The monk is bad at fighting and isn't all that wise. I’ve taken advantage (disadvantage?) of custom backgrounds, the variant human race option, and monstrous races from other 5th edition books to make these characters as bad as possible.
They each have a backstory that shows how they got to this state, and it's often a tale of woe. Some of these characters are complete assholes and deserve to suck at their profession. Others are unfortunate victims of circumstance.
Most of these characters have a high constitution. I'm not trying to say that constitution is a useless attribute - higher constitution scores are good - but it's not essential to any class, it isn't a prerequisite for multiclassing, and usually only gives you a few more hit points and a better chance on some saving throws. After all, a battle is won when your opponents are dead or defeated, and if you can't effectively overpower them, a few extra hit points aren't going to help.
These characters have all been made by the official WotC Adventurer's League standards (legal custom backgrounds, only one book besides the PHB), so you could play these poor bastards in an AL game if you wanted.
Now meet Bethyl, Dinki, Jeggory, Prizella, Shump, and Weynard.
Bethyl
Bethyl Character Sheet PDF
Bethyl is a very old hermit woman. She spends her time in small hut in the Neverwinter wood. She is obsessed with health and purity, and as a result is very healthy, but also very skinny. She has her own peculiar system of living, with a very restricted diet and a constant regimen of strange exercises and self-defense techniques; none of this serves to make her stronger, but it has contributed to overall great health. She knows druidic secrets she claims was taught to her by the trees; she uses these powers to purify her daily meal. She claims the fish and the rabbits taught her how to fight. When she is challenged on any of these beliefs, a terrible argument ensues. For fun, she sneaks around the forest trying to find people and animals, so she can lure them into conversation with a few magic tricks, then segue into preaching her way of life and selling her herbal poultices.
Dinki
Dinki Character Sheet PDF
Dinki is tiny, even for a kobold. Smarter than most kobolds, she had the misfortune of being fully aware of how poor her situation was, being a tiny weakling even amongst weaklings; this cursed her with a terrible and bitter rage. Dinki was part of a travelling kobold gang that would attempt to distract travelers along the Blackford Road with tricks and performances while the others picked pockets and looted saddlebags. One such occasion she was caught stealing from an old lady, who severed her leg with a meat cleaver. The other kobolds ran in terror, leaving her behind to fend for herself. After making herself a peg leg, Dinki has vowed to get revenge on old ladies, kobolds, and anyone that could be perceived as better off than she.
Jeggory
Jeggory Character Sheet PDF
Jeggory was a big strong street thug from the city of Luskan. One ale-soaked drunken night, Jeggory wandered out into the wilderness, stumbled into a ring of mushrooms, and interrupted a fae dance contest. Jeggory attempted to impress the faeries with some lewd thrusting, and demanded they teach him magic. They agreed to teach him some of their magic, but it was a trick. They sold Jeggory to a green hag, who took him to the faewild. The hag agreed to teach him magic, but nothing else; to get food and water, he had to sell his eye, his ear, and years of servitude to the hag; he also had to agree to a pact to never wear metal again, as a true druid would. After decades of cooking, cleaning, picking herbs, and fixing the hag's stuff, the debt was paid and he was free to return to the mortal world, having been taught a hard lesson about making deals with the fae.
Prizella
Prizella Character Sheet PDF
An ambitious entertainer with delusions of grandeur and a terrible personality, Prizella is a healthy and attractive young woman, but completely undisciplined and untrained. She inherited a lute and magical talent from her ancestors but is only moderately proficient in both. Prizella is otherwise reprehensible and cruel. Without exception she resorts to violence and backstabbing when faced with criticism, rejection, or anything short of worship. People quickly learn to do what it takes to get her to leave, or at least get her drunk until the town watch can deal with her.
Shump
Shump Character Sheet PDF
A cabin boy on a fishing ship, Shump enjoyed a peaceful and simple life, until the ship was taken by vicious pirates in a bloody slaughter, who then enslaved the surviving crew. He lived as a slave, spending the daylight hours doing the most menial of tasks, and spending the night hours locked in a closet full of books - he had nothing to do but read the tomes that filled his closet space, including a spellbook. Shump eventually became more knowledgeable in various scholarly subjects, including wizardry. It took years, but Shump taught himself all the spells in the old wizard’s tome, and though he wouldn't know it, the spells were varied and random, not particularly useful for an adventurer. One of these spells did allow him to charm a guard and escape. He has vowed to never do anything strenuous again, and if possible, get servants of his own. His plan is to use his meager magical talents to trick people into giving him what he wants.
Weynard
Weynard Character Sheet PDF
Weynard is a very young noble boy from Neverwinter. Sickly and bed-ridden since birth, his most recent birthday present was a visit from a elven herbalist, who used powerful potions and spells to improve Weynard's health. Now that he is no longer bed-ridden, he has been kicked out of the family manor, forced out into the wilderness, and must either return covered in glory or return not at all. He now serves as squire to Rogaran, a great archer, and carries all his weapons, but is terrible in battle. Rogaran has Weynard training constantly on the craft of ranging - balance, acrobatics, stealth, and archery - but the squire has made little progress. He does enjoy feeding his rations to animals, however.
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