D&D 5E Your Most *Fun* D&D 5e Character

Darrin Witchlove is a Urchin Background 1/2 elven Dex-based Oath of Ancients Paladin/ Lore Bard. It was my first 5e character to last to the end of a campaign (only level 10, but a good run). It wasn't until after I retired him that I learned that palibards (along with sorcadins and pallocks) are considered the cheesy multiclass.
 

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I've been playing for too long to have a simple answer.

Favorite character playing or seeing played currently: That's Academ Ser Trellet, a halfling cleric in my 13th Age game. (That's d20 OGL, close enough to count.) He's more of a Victor Frankenstein type then a cleric, and we've switched anything holy over to lightning. He's condescending and morbid. Speaks softly with a Germanic accent that becuase it's such the opposite just lightlights how creepy he is. It's great fun.

Favorite character I've ever run was Songmaster D'Gatham Spindleford of Cormyr, a AD&D 2nd human bard who dual-classed over to cleric of Milil. Played from 1st to epic levels, back in 2ed where high levels was better part of a real-life year to advance. But he was so fun because I played him for over a decade and of all the adventures and soap operas he had. I don't know that inherently he was fun if transplanted outside all of that.

Favorite 4e character was a rather slow speaking Warforged Warden in Eberron named Measure. He was somewhat broken, and while most of the time he was a phlegmatic NCO, during storms he got all bizarre almost drunk and talked more like River Tam from Firefly on her weirder days. But it made sense to him. For example, one comment was "Without feet we have no past." When questioned after the storm he said that he said something to the effect of "get their boot to object read" (a common tactic we did).

Eh, I could go on, that's enough for now.
 

The most fun character I've played so far was a level 5 Mountain Dwarf Rogue Assassin with the Soldier background, the Shield Master feat and (due to a little luck) a pair of gauntlets of Ogre Power. He was played as a front-line fighter specialised in dirty tricks, rather than a traditional rogue - so bonus actions mostly used for the shield bash or disengage to move about. Of course, he had expertise in Athletics, so had +10 bonuses to grapple and shoving. The Assassin bonuses kicked in a few times, too, and fit the playstyle really well. It worked even without the gauntlet, but with the extra strength he was a bit of a monster. Shame it was for a one-off, really.
 

My favorite 5e character is my drow Rog 9/Wiz 2/Brd 3, Soveliss Xiloscient. On our Spelljammer, he's the crew's intelligence/security officer, and I've placed a premium on avoiding magical detection with him. My goals are to have a character who can contribute meaningfully to all three pillars of play and who is immune to divinatuon magic 24/7, and with the right items and spells, I'm pretty much undetectable by magical means and have something like a +18 to my Stealth.

- Rogue/Arcane Trickster - good spells, excellent class features, and pretty great damage for a character with only one attack. A familiar for advantage and booming blade keep my damage competitive, and there are so many uses for improved Mage hand. I just got Spell Ambush, so I haven't had a chance to check it out in play yet
- Wizard/Grey Guild ( from Sterling Vermin Adventuring Co) boost to spells, ritual magic, and the class feature that makes people forget details of their interaction with you on a failed Int Save. Plus no spell book needed.
Bard/College of Lore - more proficiencies! More expertise! Magical secrets! I plan on taking the rest of my levels in bard. Charisma is low for my level (16), but between spell ambush and cutting words, I think I can make my spells stick.
Feats: Observant, Skulker
Magic Items: Amulet of Proof Against Location/Detection, Ring of Mind Shielding, Dagger of Warning

I'm also playing a Half-Orc Devotion Paladin in CoS. Very fun, the perfect character for the game, but we've only played a couple of times and I haven't had a chance to test his capabilities yet.
 

Been playing a Barbarian Berserker for 80 odd sessions now in a great Judges Guild Wilderness of High Fantasy setting game. No feats and a lovely old school feel. Hakeem is just indomitable. No armour, big sword, nothing flash, he just will not give up and so far blind luck has seen him through (along with the Relentless Rage ability on more than one occasion lately). Sometimes not thinking too much is a real joy.
 

So far, I've only had the chance to play one 5E character. He's a half-elf vengeance paladin of Helm. We're playing in a Realms campaign. So he's from Cormyr. He was orphaned in a raid as a baby and adopted by a soldier in the Purple Dragons. I went great sword as my weapon of choice and soldier background. He's been a blast to play. I'm really quite impressed with the versatility of the paladin class in 5E. I can fight well and deal big damage when it's needed. Though I can also help out the cleric with healing and support if he starts running low on spells or drops. The bonus skills from backgrounds and being a half-elf really help a lot too. So I have something to contribute in any situation. Plus the divine spells paladins get are pretty helpful too. Being able to cast Command has saved the group just as well as any smite. Being able to summon up my own mount is great too. I enjoy figuring out the best strategy for my paladin in any situation. Since I have good charisma and some social skills, I kind of end up as the party face too. So I'm never bored. There are tons of ways I can help out.
 

So far my play has been minimal since I normally DM, but I did create and play a wood elf monk of te open hand. No crazy feats or anything. He has the criminal background, and was basically on his way to a life of crime before an old master took him in and taught him the ways of the monk. The master is an old drunk who no longer gets involved in anything himself, so he sends the monk in his place.

Tons of fun in combat...the options when he flurries are great. His shining moment was when he was able to make his way across a bridge between two towers, and he launched three trolls off the side of the bridge. Avoided a ton of combat for the party, and allowed them to move on to their goal in te tower.
 

Willem Thigair, half-elf Bard. Father is an Eladrin wizard, mother is a human Traveler. Has a human half brother named Saethwr, a tiefling half sister Moira, and an indeterminate number of other siblings. In 4e he was a cunning bard swordsman, in 5e he is a bard/warlock with a custom subclass based loosely on the rogue swashbuckler.

In either case he is a master of the sword, and of taunting and cursing his foes, and too damn pretty for his own good. He was an airship captain at one point, before crashing it in a fight with a living storm, and is currently leading a resistence movement in Abeir, while trying to find a way home to Toril.

In 4e one of my favorites was my buddy's gnoll artificer, and also his kobold wizard. My wife's gnome artificer/theif was really fun, as well. And she had a gnome Star pact hexblade French aristocrat in an alt earth campaign that was just the best. Same campaign where I had a Shadar-kai prince of the British Empire, privateer captain, "black prince" character.

The most fun character I've made in 5e without any conversion from 4e would be my netherese Paladin/monk sea knight.
 

Last night, I played my bearbarian grappler "Immovable Rod" Manleigh again in a Warhammer 40k-ish homebrew where we're agents of the Emperor. As a folk hero, he's known for being the champion of Lawfulmania XXIII. I play him like a luchador and use a lot of improvised weapons - whatever happens to be around at the time. Luckily, the DM is generous with me finding folding chairs.

Tonight I play a 5th-level monk in a one-shot where we are agents of the Zhentarim. His name is Wei of the Shadows, but he's a charlatan and his persona is that of the wizard Arcain the Illusionist. I took Magic Initiate to give him a few cantrips to round out the illusion. The other players don't even know he's a monk and I aim to keep it that way - until someone gets up next to me and I give them a beatdown with my quarterstaff!
 

There has been no standout in either direction: They've all been great... Modianger, the Dwarven Barbarian; Cruddles the Deep Gnome Enchanter; Thotmose, the Human Warlock/Monk; Galen Dracos, Human Pole arm Paladin; Ureas Font, a 'human' sorcerer with a fascination with necromancy; Myrder, Human (Extremely Evil) Ranger/Rogue; Roth, Human Cleric of Thor / Bard; Dryken - Elven Ranger5/Fighter4/Wizard 2/Rogue X - versatile.

Every PC has been effective, fun and versatile. Honestly, the biggest differentiation in fun has been how ebjoyable the personality of the PC has been.
 

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