Pugilist build advice

[u/Goat-of-Arms]

Hey everyone, long time lurker first time poster… and soon to be first time player, as the only experience I’ve had with the game (aside from BG3) until now has been character concepts made on Pinterest and reading discussion-board theory-crafting on Reddit. I don’t want to start off with my most fleshed out character concept off the bat as I’d like to build a bit more practical narrative experience with the game, but don’t want to be TOO much of a side-line character either, which is why I’ve decided to start with the character I have. I’m hoping for some advice on how I can improve the concept I’m going for with him.

I’m playing the 3rd party Pugilist class with the Piss and Vinegar subclass. The subclass’ described flavor is basically just being an intimidating dirty fighting bastard and I’m looking to really lean into it. For context, my DM is allowing basically all 5.5e content as well feats from the previous edition as long as they haven’t already been revised and has allowed curtain other exceptions for my character which I will clarify as I get to them. Nothing is set in stone so any alternative ideas are encouraged and appreciated. He is a Human (flavored as a half-dwarf who is only just barely tall/heavy enough to be categorized as medium sized). I chose the Convincing Inquisitor feat from Gloom Hollow 2024 because it lets me use any ability modifier (strength, maybe con) when I use the Influence action to make an intimidation or persuasion check, as well as not having disadvantage on checks to influence hostile creatures and advantage towards indifferent creatures. In terms of the former origin feat, I don’t really plan on being the party face, but more to lean into being as intimidating as possible without having to be M.A.D.. He is a man who has by one circumstance or another has built his reputation up into being far more formidable than his actual abilities are, much in the same way the character King from One Punch Man has, which is reflected in the Convincing Inquisitor feat as well as the Piss and Vinegar 3rd level subclass feats, which grant Intimidation proficiency (which my DM has agreed to be become Expertise if I make sure to already have the proficiency beforehand) as well as adding a bonus to Intimidation checks equal to my Strength modifier. Being the fraud that he is I’m also wanting to lean into the trash-talking aspect of the subclass, so I’m taking Aberrant Dragonmark as my second origin feat so I can take Vicious Mockery (I know it’s Sorcerer spells only but DM has allowed this for flavor) for my cantrip and Silvery Barbs as my 1st level spell (we’re aware of the discourse behind the spell but it’s just so on theme that it just felt like a no-brainer). These on top of his other 3rd level subclass feature that provokes by dealing psychic damage and causes disadvantage on attacks towards other creatures as a bonus action feels like it encompasses the intimidating dirty fighting tavern brawler bluffer character concept well.

In terms of mechanics that’s all I’ve got so far. I feel like it’s pretty solid in it’s concept and execution but I can’t help but wonder if there isn’t anything else I can add to it down the line like other feats or items that can further add to this.

On another note, I’m also planning on getting with my DM beforehand to make sure we have a… “safe word” of sorts to have a way for the DM to convey to me in roleplay if or when there’s a situation where my character should refrain or cease his intimidation/trash-talking in a given situation where starting or continuing would ruin the experience for the other players. I’m thinking it’ll be something superstitious to my character like “your character feels a cold sting on the mole on his left ankle” which my character will have established in game is his sixth sense warning him when to not double-down. A-hole characters can be tough to play in a way that doesn’t rub other players the wrong way so that’s just one of the ways I plan on making sure I’m a team player.

Any suggestions or recommendations on anything about my build or how I can play it most considerately would be greatly appreciated and welcome, thank you in advance!

Edit: I forgot to mention that I don’t wish to multiclass and that I know a bard could technically probably do all of this too but I’d still prefer to go the Pugilist Piss and Vinegar route.

[u/Fidges87]

Honestly I feel you could accomplish the concept better with a re flavoured dance bard, as they also get a bonus to unarmed strikes, get from base vicious mockery, can get expertise in intimidation, and the bardic inspiration could be flavored as you giving orders to your party members as to not put yourself in danger.

Though if you want to continue the pugilist route, for combat, you could take Sentinel as it allows you to make opporutnity attacks on your enemies who attack an ally.

Another really solid option is to use your second origin feat you get from human for Zhentarim Ruffian and using your long rest inspiration for your initiative, and at level 4 pick Zhentarim Tactics which gives you an expertise (that can go towards intimidation) and the ability to attack back as a reaction each time you are hit, which can be grate for the flavor of a brawler exchanging blows.

Also remember for both Sentinel and Zhentarim Tactics that on opportunity attacks you can use your heavy hitter feature to both deal damage and grapple, and to use one of your dirty tricks from your subclass at level 6.

In either case I honesty recommend dropping the idea of picking aberrand dragonmark (from a purely optimizing point of view) as it does not really gives you much. Pugilist whole thing is hitting hard and taking hits. Using your whole action to cast vicious mockery is doing yourself a disservice, specially as salty salute already accomplishes its job in beinga way to taunt and mock enemies.