Your definitive build

[Renvir]

I don’t think i’ve been more satisfied then when the DM allowed my Matador-themed Sword Bard to grapple Minotaurs using his expertised Performance skill. It was exactly the kind of thing i wanted to do with that character, and i did fulfill that.

That's a DM Hall of Fame move.

As for my quintessential "me" characters, I'd go with Oberon, the Human Land Druid 10/Rogue 1. He was a very go-with-the-flow kinda guy. You want to stealth ahead? I'll wildshape and provide a second set of eyes. You need a desperate heal? I've got you. Need some guidance or Guidance? You'll find none better. Locks need picking? My 11+1d4 should work. Something needs a butt-whooping? I've got a myriad of spells to make that happen. Just a real team player who did not need the spotlight.

The other one is Julius, the Dragonborn Evocation Wizard. He was a DMPC that showed up every once in a while to provide exposition and lead the party's Dragonborn allies in battle. I had him level along with the party up to 15. He spent every feat on armor upgrades so by the end point he was tossing around fireball, cone of cold, and lightning bolt while wearing full plate. It's a mark of Julius' awesomeness that the players would seek him out from time to time without my prompting.

[Arkhios]

Another quintessential me I've yet to play with 5e (I did play him in playtest though) is human mage, born to a nomadic people who knew nothing to teach in terms of arcane magic and very little of any other either. Original concept was that he'd been born blind during winter storm, and had inherent talent for magic, but had received a blessing of sorts that allowed him see "normally" due to "perceiving the world through the Weave" (similar to Neo from Matrix after his eyes got burned out).

That was, however, before I got into playing D&D in the first place as he used to be originally a character in a novella I wrote back in school (inspired heavily by Raistlin who was described as having poor health, and Neo who eventually received a supernatural ability to overcome a serious impairment, as well as the circumstances of my own birth; it was -43.6° Fahrenheit in southern Finland that day, and I have pretty hefty visual impairment for my age for reasons unknown to me).

Also, I was around 15 yo. back when I wrote it.

Later the character concept evolved quite a bit and I dropped the blindness-from-birth aspect, as it would've made wizarding rather difficult (I don't think he'd be a sorcerer).

Anyhoo, Aistarkhios the Stormbearer was to become the greatest Archmage of his age, and a master in magics that revolved around... Well... Storms (still, not a Sorcerer!).

Due to his background, he would have at least Light Armor proficiency, maybe even medium, and could handle hand-to-hand combat reasonably well, even though his true strenght lies in powerful magic.

As a 5e character he would be a variant human (with lightly armored as 1st-level feat)

[Warlush]

A halfling, fiendlock, pact of the chain.
Obviously I had an imp, and obviously the hijinks were for real.

[Danielqueue1]

I've played a lot of characters, there are some I have loved role playing, there are some that I loved the mechanics of. There are some that hold a special place in my memory, but the build that is the most "me" has got to be Tearn

Tearn is a standard human path of ancestors barbarian / war wizard who was originally a bookbinder but picked up his ancestral sword to defend his home against zombies and is now haunted by his ancestors. Usually uses spells defensively, making him very hard to hurt meaningfully when not raging. when raging he makes it hard to hurt his allies due to ancestors. Kind of a dr. Jekyll and mr. Hyde thing going on. There's a surprising amount of synergy with arcane deflection working even while raging and mirror image remaining active while raging. Sure it isn't optimized, but it is freakily resilient and I am all about weird combos that shouldn't work, but somehow do.

Current set up,
Resilient (Wis)
Adamantine half plate,
Ring of protection
+1 shield
Ancestral sword (+1)

With advantage on Dex saves, profficiency in Con and Wis (resilient feat) and a reaction to get +4 means he's good at saving throws, has good armor, and a use for his reaction every turn. And his rage features mean big guys want to target him. It's fun.

[Hairfish]

A half-ogre (statwise, just a reskinned orc) war cleric of Kord. Sage background with INT as a dump stat, so he usually didn't know anything about a given subject, but knew someone who did. A cheerful idiot that loved to learn about new things, but wasn't great at being able to explain them later. Had a very open, possibly heretical, view of what counted as "strength"; for example, smart people were "strong in the head". Talked like Detritus the troll from the Discworld novels.

[Random Dice]

Forge Cleric 1/ Divination Wizard 19. Name: Random Dice. Race: Variant Human

[W41Blackr4zr]

my first ever character is an assassin halfling
he went through so much over the years that no other character i have made is quite the same
he was know as the jumping rogue because he could never find a trap to save his life
but he always managed to jump out of the way.
best combo was when the half-orc ranger threw him at the enemies
he grew a scorpion tail at one point. was killed by a doppelganger and impersonated at another (the DM had me playing the doppelganger for about 8 sessions until we figured out that the halfling actually was actually alive and well).
he lost all his memory and had to learn everything again at about level 15
no other character is quite the same

[Captain Panda]

My favorite character? Moon druid. Not just for the power, they eventually get outclassed by the wizard, but because it's a lot of fun having both the power of nature behind you and being able to unleash your inner, rampaging panda bear!

[Yakmala]

Tough choice, but probably my streetwise back-alley doctor, Morgan Murphy, a Variant Human Thief with the Healer feat. No matter the situation, he has something to bring to the table. Keep the party alive? Check. Scout/Sniper? Check. Party Face? Check.

I didn't think much of the Thief when I started playing 5E, favoring the Swashbuckler instead. But after playing Morgan through a months long campaign, I'm totally sold on them. Fast Hands is amazing. It never stops being useful.

[MagneticKitty]

Moon druid. Probably Tabaxi or dragonborn as race.

Since you said unoptimized those are my favorite races flavor wize... But they don't fit druid... and dragonborn is kinda under powered. And my female dragonborn would not have mammalian features. Because that's just weird. And also have a tail because I said so.

[ChildofLuthic]

Tirthera, a wood elf battlemaster who used a rapier and, occasionally, a crossbow. She loved hitting things with her sword so much <3

[ZorroGames]

Glensman (“Glenn’s Man”) in 0D&D was my first character to make an impact after getting out of the campaign of the murder hobo DM that was my first experience in the game. Rolled 3D6 in order. Human Cleric. Basically a PJ (Pararescue Jumper for those who remember) who was the “sidekick” type to the Fighting Men in the parties and who trembled around lycanthropes and nearly went rage behavior around undead. Cleric of Seker the God of Light from “AEgyptus” the Egypt clone nation. Retired twice, finally around 16th level in 0D&D stats. Looking back it was me except not so intelligent and way wiser. Still have the character data for him and his partners.

Second best were a bevy of Dwarf and Human fighters and clerics from AD&D during the follow on years until Janice and I adopted girls from India.

Long hiatus followed until 5e.

In 5e I have spent my whole time until now experimenting and trying out tons of multi-class experiences. Have not found a campaign close (night driving is a challenge now) enough or interesting enough to pick my one character since moving away from my original AL shop but I would like to focus down one of on three concepts that really have grown on me this year.

But that is another thread.

[Evaar]

It's Dueling, shield and rapier Eldritch Knight for me.

I played one of those at first but didn't really grasp how to use the magic effectively, I kept jumping around and finagling and adjusting trying to get it to be something it wasn't really, then when Hexblade came out I swapped to that and it seemed right for the character. But now if I got to play it again, I'd just go straight Eldritch Knight.

I like just having a massive AC without heavy armor, I like dishing out damage as a one-handed weapon and shield user, and I like having a selection of clever spells I can use to accomplish things much more powerful than a Fireball. I like being as good at stealth as anyone but the true expert. It feels like a character that can do almost anything.

[Keravath]

The closest I have come would be a human 1 knowledge cleric/9 evoker wizard. He is an academic who studied magic and magical lore as an archivist at the temple of Mystra in Waterdeep for more than a decade before realizing that they would never reach the level of understanding of magic that they wanted without actually practicing magic. They started studies as a wizard and discovered the need to apply the knowledge in the field in order to truly master their understanding of magic so they started going to the Yawning Portal in order to meet the appropriate sorts of people. After some adventures in Waterdeep and exploring a few levels of the Dungeon of the Mad Mage, he has now travelled more widely with adventures as far apart as the Moonsea region, Chult and one of the planes of hell.

[Mjolnirbear]

My favourite was Lord Charuk, a Waterdhavian Noble Half-Dragon (reflavoured dragonborn) and tomelock. He was so much fun throwing his weight around as nobility, and playing up his various flaws. But even more importantly, while my warlock spell slots felt crazy restrictive, he had *all the fun cantrips* and that was amazing.

Heat wave in Baldur's Gate? Chill my drink.
Unfortunate mess on my new boots? Cleaned!
Need an item? Make it out of ice.
Let's use Minor Illusion instead of RL photos to find clues. Use Mending at every opportunity. Mage hand whenever I liked. Mold Earth for tunnels, earthwork cover, traps, jails, hiding evidence.

[Evaar]

The closest I have come would be a human 1 knowledge cleric/9 evoker wizard.

This was my 2nd place pick, though he was an abjurer. It was extremely fun to play, but sadly met an early death due to a crazy scenario I won't get into here.

[Dr paradox]

Roman Waldemar. Level 5 Human Fighter with the Charlatan Background and the Actor feat. A con artist and a borderline pathological liar. Everyone kept forgetting that he wasn't a rogue, and they'd ask him to sneak places or pick locks, and he'd look at them funny. Granted, he wasn't great at fighting - I gave him a longsword and no shield, because I liked the idea of versatile weapons and he felt like he ought to be scrappy, grapply, and climby. He lost his sword when he dropped fighting some gnolls and the rest of the party had to carry him away, but he picked up a battle-axe that kept him going just fine.

I didn't play Roman long, but he was a ton a fun, because I love playing liars. That might come out of the fact that I rarely play as a character, generally being a DM, so choosing a character who was, himself, prone to "role-playing" as a bunch of different people appealed to me. Even "Roman Waldemar" was an assumed name, his real name was Leon, not that the rest of the group ever found out. He bounced well off of another character in the party, a comically thick-witted Paladin named Mercer.

[Pex]

Pathfinder Life Oracle

[JackPhoenix]

Human rogue 2/wizard x. School doesn't really matter, but marked preference for conjuration, necromancy, enchantment and illusion spells. Not that I ever got to really play one, being eternal GM....

[ZorroGames]

Pathfinder Life Oracle

Pex,

That tells me absolutely nothing. Never played, read, or watched a PF game. Probably never will because of who I know who plays the game locally. Bad JuJu of the first water.

Can you express that in terms I might understand?

[HPisBS]

Way of Tranquility.
It just screams "Zero Aggression Principal"

[Wildstag]

The clear answer to this for me is the classic Swashbuckler3/CollegeOfSwords5/Battlemaster12, which fits the quick Errol Flynn style swashbuckler best in my opinion, but high level builds that need 12 levels to get going don't really feel right.

The one I'm most content playing though, that when I look at it, I feel like it fits exactly like what I want to play, relies on old UA that never saw the light of day.

It's a character, probably Hill Dwarf or Wood Elf, that takes one level in Sea Sorcerer followed by levels exclusively in Fighter for Eldritch Knight. At level 4 it takes the Magic Initiate Feat for the Druid Spell-list. From it you get Shillelagh and Thorn Whip, and Cure Wounds (or whatever, it's the cantrip that matters). At level 6 you take Sentinel. You do NOT need any Charisma for the build to work, just Wisdom, Dexterity, and Constitution.

From Sea Sorcery you use Curse of the Sea liberally. Whenever you cast Thorn Whip and hit, apply the Forced Movement effect. This means that you can hit a target 30 feet away and move them up to 25 feet towards yourself. From there, you smack them with your bonus action attack (level 7 Eldritch Knight). If they try to move away from you, swing that Opportunity Attack. If they get hit, they lose the ability to move away from you. It's almost like the Lancer ability from TERA where you leash someone.

Anyway, it's sad that Sea Sorcery never made it into a printed book, because I love this idea so much. I love the idea of whip-users, and this one relies on my favorite cantrip to work its magic. Without the UA, I play it as a straight Eldritch Knight and target foes within 15 feet of me with Thorn Whip.

[Arkhios]

Pex,

That tells me absolutely nothing. Never played, read, or watched a PF game. Probably never will because of who I know who plays the game locally. Bad JuJu of the first water.

Can you express that in terms I might understand?

Not my character, obviously. But having played Pathfinder for over a decade I'm fairly sure I'm familiar enough with the system and its classes, to be able to chime in!

Spoiler: A little bit of background

Show

If you don't know anything about Pathfinder and it's spiritual predecessor 3.5 edition of D&D (what you see below is true about sorcerers and wizards in both systems):

Sorcerers and Wizards shared the same spell list almost entirely (with only a few exceptions being wizard only).
The main difference between wizards and sorcerers was that Wizards prepared their spells at the start of every day, while Sorcerers simply knew their spells and could cast those same spells every day.
Wizards had fewer spell slots available, but could theoretically know all the spells in their spell list. Sorcerers knew only a handful of spells, but had more spell slots per day than wizards.

Oracle is like a divine Sorcerer in Pathfinder.

Cleric and Oracle share the same list of spells, but while cleric had to prepare spells every day and had fewer spell slots, the Oracles knew only a handful of spells from their spell list and had more spell slots per day to cast them from.
Unlike Sorcerer, however, Oracles had proficiency in armor and could cast while armored without any trouble.

Oracles had a very interesting mechanic in that on one hand they had a debilitating curse which bestowed them several drawbacks, but also granted them some beneficial abilities in return. In addition, each Oracle chose a Mystery that has been revealed to them (kinda like Clerics had Domains). Along with some Mystery Revelations (functionally same as Warlock's Invocations, but all of them tied to specific Mystery), oracles received bonus spells known from their Mystery. Life Oracle therefore had been revealed the Mystery of Life, which gave them all the juicy healing spells and generally made these Oracles function even more similar to a Cleric than other oracles, except it still casts spells almost like a sorcerer. Since Pex left out their Oracle's Curse (there were more than one available curses to choose from), it's impossible to explain further on that.

So, basically, if I had to convert an Oracle to 5e, I would say it's a Sorcerer with the Divine Soul Origin (from Xanathar's Guide to Everything), with proficiency in armor (preferably medium at least). To better mimic the curse aspect, I'd say it must have the Haunted background (IIRC, from Curse of Strahd), the Aberrant Dragonmark feat (from Eberron: Rising from the Last War), or both.

[ScoutTrooper]

Monk; Drunken Master

[ZorroGames]

Not my character, obviously. But having played Pathfinder for over a decade I'm fairly sure I'm familiar enough with the system and its classes, to be able to chime in!

Snip spoiler

Oracle is like a divine Sorcerer in Pathfinder.

Cleric and Oracle share the same list of spells, but while cleric had to prepare spells every day and had fewer spell slots, the Oracles knew only a handful of spells from their spell list and had more spell slots per day to cast them from.
Unlike Sorcerer, however, Oracles had proficiency in armor and could cast while armored without any trouble.

Oracles had a very interesting mechanic in that on one hand they had a debilitating curse which bestowed them several drawbacks, but also granted them some beneficial abilities in return. In addition, each Oracle chose a Mystery that has been revealed to them (kinda like Clerics had Domains). Along with some Mystery Revelations (functionally same as Warlock's Invocations, but all of them tied to specific Mystery), oracles received bonus spells known from their Mystery. Life Oracle therefore had been revealed the Mystery of Life, which gave them all the juicy healing spells and generally made these Oracles function even more similar to a Cleric than other oracles, except it still casts spells almost like a sorcerer. Since Pex left out their Oracle's Curse (there were more than one available curses to choose from), it's impossible to explain further on that.

So, basically, if I had to convert an Oracle to 5e, I would say it's a Sorcerer with the Divine Soul Origin (from Xanathar's Guide to Everything), with proficiency in armor (preferably medium at least). To better mimic the curse aspect, I'd say it must have the Haunted background (IIRC, from Curse of Strahd), the Aberrant Dragonmark feat (from Eberron: Rising from the Last War), or both.

Thanks, Arkhios! Much clearer.

[Sam113097]

Brohm, a half-elf Battlemaster Fighter that is a failed paladin. Not a fallen paladin, just an acolyte that trained to become one but was unable to dedicate himself to the lofty ideals of a paladin's oath and resorted to adventuring. I took the Healer and Mage Initiate: Cleric Feats with him to make him the party's healer, and he did some major damage as well with Polearm Mastery. Very fun to play, he was a good person that was grappling with his failure to live up to his life's goal and find another one.

[ZerohFG]

I used to say 1/19 rogue/lore bard. Skill monkeys are fun. I however love my new Eldritch Knight/Battle smith artificer (with death cleric and fiend warlock dips). I just wish I could make it work better with standard array for when I don't get to roll stats. It runs all combat attacks and spells through INT thanks to battle smith and has war magic to cantrip/attack combo, but the gimmicks come from the cleric and fiend even though i only grab none combat skills from them. Toll the deadX2, then whack something in the head with a flail can never not be fun.