So I know @danryckert wants to be Ric Flair, and there has been some suggestions he should just get with the program and play a straight up fighter. However, D&D has a long history of having grappling as a viable alternative, and rather than shoehorn him into a type of character he doesn't want to play I thought I'd post some recommendations for his character that might instead help facilitate both his desires and do so through the rules.

To that end @rorie, here are some suggestions for his build.

Richard the Horseman @ Level 1 would look like:

Ability Scores:
STR: 14 +1 from human, +1 from Tavern Brawler.
DEX: 10
CON: 14 +1 from human.
INT: 10
WIS: 10
CHA: 12

(These rolls are from the unpluggeds, with some modifications from changes in the build. This is assuming the optional human variant is used that grants a feat, and only +1 into two scores instead of all of them. I also moved the 12 from his reroll into charisma since he wanted to be a charismatic fighter.)

Hit Points:
12

Proficiencies:
Armor: All armor, shields
Weapons: Simple weapons, martial weapons
Tools: Disguise Kit (Entertainer), Musical Instrument: Lute (Entertainer)

Saving Throws:
Strength, and Constitution

Skills:
Acrobatics (Entertainer)
Athletics (Needed for grappling)
Intimidation (Intro)
Performance (Woo!, Entertainer)
Persuasion (Human Bonus)

Feats:
1st Lvl: Tavern Brawler (Stat increase into strength, taking it from 15 to 16.)

Fighter Special Abilities:
Fighting Style: Dueling*
Second Wind

(* as a DM, Rorie could choose to make a custom style here to fit the character, here is a suggested variant: Unarmed Brawler: Damage dealt while wielding no weapons is treated the same as if a Monk of equal level. At 10th level it grants the brawler the benefits of Ki-Empowered Strikes. This would grant him scaling unarmed damage, and the ability to get past magic DR, though none of the other benefits of the monk's martial arts. Personally I think it helps the character fill the role desired by the player in a way that isn't over powered.)

Background:
Entertainer - Gladiator Variant
Feature: By Popular Demand
Personality Trait: I get bitter if I'm not the center of attention
Ideal: Greed, I'm only in it for the money and the fame.
Bond: I will do anything to prove myself superior to my rival.
Flaw: I'll do anything to win fame and renown.

Equipment:
Chainmail, Martial Weapon, Shield, Light Crossbow & 20 bolts, an Explorer's Pack, Lute, Costume, gold pouch with 15gp.

Future:
@ 4th level I would consider the Mage Killer feat, this will make you very deadly to casters and increase the viability of grappling
@ 8th I would suggest the Grappler feat, which further will enhance your abilities.
@ 12th+ Pretty free to do whatever you want at this point, You'll want to max strength and likely increase your con after. If you take strength at 12 and 16 you'll then have a feat free to either add +2 to your con, or pick up something like Durable, Lucky, or Tough. I would probably pick up Lucky or Tough myself.

Understanding The Grappler

So important to playing a grappler character is to understand the benefits of it. By default in 5e the only main benefit is that you apply the grappled condition to the creature, this allows you to continue to attack it, and they cannot get away. By itself this is useful for trapping squishy enemies like mages, who want to get away. You can also move a creature you have grappled up to half your movement, this could potentially save an ally who are themselves trapped in a bad situation.

Combined with Tavern Brawler, grappling becomes a bonus action, you don't need to do anything but strike the enemy. And once grappled to can continue to strike them. To do wrestling maneuvers, simply narrate your actions appropriately. A unarmed strike by you against the enemy can be told as if you are doing a german suplex, figure four, etc.

At higher levels with Mage Killer, you can then also really take the pain to enemy spellcasters, forcing them to provoke attacks to cast a spell, and then having to save against them or lose their spell. You can effectively shutdown an enemy caster, often among the most lethal opponents.

Advantage/Disadvantage

The DM can also decide that circumstances influence a roll in one direction or the other and grant advantage or impose disadvantage as a result.

Player's Handbook

Another potential advantage to grappling is, well, advantage and disadvantage. If you have a creature grappled and instead of attacking you it wants to attack a weakened comrade, nothing prohibits it from doing so if it is within range, but the DM might say it would be at disadvantage to do so, after all he is locked in combat with you and cannot freely maneuver. Likewise you might gain advantage when attack a creature you have grappled, after all that is your specialty. This isn't a hard and fast rule, and up to the DM to decide if it would be granted one way or another, but it would be an easy case to make for it in my opinion.

Knowing Your Role

A grapple roll is going to always be a 1d20 + Ability Score Bonus + Atheltics, with this build at level 1 it is: 1d20+3+2, it is equal to his attack roll. It is opposed by the targets Strength (Athletics) or Dexterity (Acrobatics), as chosen by the target. The grappler may end the grapple as a free action.

To escape a grapple you basically do it in reverse, with a Strength (Athletics) or Dexterity (Acrobatics) check opposed by the grapplers Strength (Athletics)

A grappled creature cannot move, but the grappler may move up to half his speed taking the creature with him, unless it is two or more sizes smaller than him. (then it is his standard move speed.)

Grappled as a condition applies the following:

• Grappled creature has its movement reduced to 0.
• It ends if the grappler is incapacitated, or if some other effect moves the grappled creature from the grapplers reach, such as with some kind of knockback effect.

Sorry OP he can do whatever he wants with his build but with a Charisma of 12 he will never even be half the man the Nature Boy is. WOOOOOO!!!!

That actually isn't a bad idea

I'd recommend not using Unarmed Brawler simply because they don't have the Player's Handbook and thus don't have the rules for Monks.

@corevi: Yes they do, they may be running the starter adventure but they have multiple copies of the PHB.

@mrwakka: Oh really? All right then. They certainly didn't help.

@corevi: I didn't say they had read them, just that they had them. =p

I would also give him the standard array for stats so he's not so underwhelming stats wise. Something like:

• STR: 15 +1 from human, +1 from Tavern Brawler. (16 total)
• DEX: 12
• CON: 13 +1 from human. (14 total)
• INT: 8
• WIS: 10
• CHA: 14

@krevee: Shouldn't that be 17 Str total?

@krevee: You could also go the con route, give a little more hp.

STR: 16 (14 +1 human, +1 Tavern Brawler)
DEX: 12
CON: 16 (15 +1 human)
INT: 8
WIS: 10
CHA: 13

Slightly reduced charisma, though still better than before, and we get a little extra HP out of it, which will add up over time. Still yours opens up some additional feat choices, like Heavy Armor Mastery thanks to the 17 strength. (instead of +4 to str you could get +3 + damage reduction against certain types of damage.)

@corevi:

Yep, I'm just terrible at counting apparently...

@mrwakka:

Yeah more Con isn't a bad idea either if he is going to be rolling around doing WWE moves on guys. Being able to survive a battle is always good.

@mrwakka: This is the kind of D&D knowledge and attention to detail that could only come from a user with Boo as his avatar. Great work and from your lips to @danryckert's and @rorie's ears. Playing a conceited wrestler is something that can work if the player knows how his character fits in the rules instead of trying to figure out ways to break the game's internal logic.

This is fantastic. Great post OP.

Brad and Dan should be working together in battle. Dan grabs them and Brad stabs them in the back.

If he wants to punch dudes and wear robes, couldn't he just be a monk instead of modifying the fighter?

@teaoverlord: Mechanics wise that's better but as a character it doesn't make sense with what Dan is doing.

@corevi: Just rename ki cool guy wrestling juice or something.

Dan doesn't follow laws. Especially ones about not slapping people.

He is behaving like a mercenary. A monk has a certain code to them.

The PHB says monks are almost always lawful. Playing a monk and just ignoring the religious order stuff seems simpler than making modifications to the fighter. Also, the entertainer background has a gladiator variant that gives you an unusual weapon instead of an instrument. Are there folding chairs in D&D?

@teaoverlord: A monk could work, possibly better, but it also has a number of trappings that Dan didn't seem down with. He didn't want any 'mystic crap' as I recall. Forcing a class change also goes against the goal of this, which isn't to tell him the 'right way' to play, but show him how to make what he has chosen work for him.

Yeah, this is basically the character that Dan is trying to play, because he clearly has no interest in being a standard fighter using martial weapons. When you have a pet idea for a character, it can be done in a way that basically lets you roleplay it properly, but until this thread, the issue was that no one involved in the Unplugged has enough experience with the rules to give Dan's character all of the abilities he clearly wants to use.

Hopefully Dan sees this and scraps his character sheet in favour of this one. Also yeah, good lord were Dan's stat rolls terrible. I wish he had rerolled them, or just taken the standard starting stats instead. You don't need broken stats for D&D to be fun, but just about any character could really use 1-2 stats where you have a 16-18 in them.

This is a good idea! Hopefully Dan and Rorie see this. I think this could help Dan get more into it.

This Unplugged has been a ton of fun so far (minus the silly bickering over 1-2 gold. Playing greedy characters is one thing, arguing about an insanely small amount of gold for 20 minutes is a whole other thing). I hope it continues for a long time. I'm very excited to see where it goes once they get past all the starter adventure/tutorial stuff.

@mrwakka: I think I am probably not going to look at any D&D stuff until after PAX East, but try to send this to me again in a PM in a couple of weeks and I'll try to go over it with Dan!

@rorie: Will do!

THIS LOOKS CONFUSING

@danryckert: Basically you punch the enemy in the face and then as a bonus action you grapple him for wrestling shenanigans on your next turn.

This seems like a really good idea. Great job duder.

@danryckert: You'll be fine, sir. :)

@danryckert: Like a lot of D&D it is only confusing at first, once on a character sheet you'll rarely see any of it, it all comes down to what @corevi said.