D&D 5E Best investigator builds

Paul Smart

Hello everyone. I am curious, what are your best investigator builds? If you were building a team of private detectives what would you make?

There is the obvious Wizard PI (AKA Dresden) build.
Some sort of tough guy / takes a beating and keeps going build, probably a fighter of some sort.

Let me know your ideas.


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My 5e PC is a Half-Elf Rogue 1/Cleric of Knowledge 1/Warlock 8 — 4 sets of Expertise by 2nd level, tons of skills trained, lots of useful at-will options from invocations, access to Guidance. I cast Invisibility on the whole 3 person party, Fly, etc...

For reasons, I'm not a Book GOO Warlock, but access to all rituals+telepathy would be great.


Heretic of The Seventh Circle
If Eberron races are available I’m partial to a Mark of Finding Half-Orc Ranger or a Mark of Detection Half-Elf Inquisitive Rogue.

If Exandria stuff is available, Cobalt Soul Monk makes a very good Sherlock Holmes. (Some folks forget that he does bare knuckle boxing in one of the original stories, not to mention parkour and single stick fighting, all of which fit Monk)


Quantum Chronomancer
I was actually just putting this together to ask for advice!

I've been doing some theorycrafting of an inquisitive rogue, planning her for all 20 levels while also considering playability as she progresses.

Rhundi is a "private eye" type character, a bit of a skill monkey with an arsenal of options for combat. Very high awareness, slippery and stealthy, and combat tricks to help with sneak attack in a variety of circumstances. Likes to mix it up in melee, but also effective ranged.

Rhundi, Stout Halfling Inquisitive Rogue17/Battlemaster Fighter3, inquisitive background (using custom lineages)

Level 1 Abilities: Str 8, Dex 16, Con 10, Int 13, Wis 16, Cha 12 (including racial +2 Dex, +1 Wis)
Level 20 Abilities: Str 8, Dex 20, Con 10, Int 14, Wis 18, Cha 12
(ASI 4th Skill Expertise +1 Int, 8th +2 Dex, 10th Lucky, 12th +2 Wis, 16th +2 Dex)​

Attack bonus: +11
AC: 20
Initiative +5 (advantage)
Sneak Attack: +9d6 (+12d6 insightful fighting)
Passive: 26 Perception, 24 Investigation, 26 Insight (reliable talent)

Skill Proficiencies: Acrobatics, Deception, Insight, Investigation, Perception, Persuasion, Stealth
Expertise: Acrobatics, Insight, Investigation, Perception, Stealth
Fighting Style: Defense
Maneuvers: Brace, Precision Attack, Feinting Attack (Riposte)

Combat: daggers (for melee and ranged), studded leather
Magic Items: dagger of warning, glamoured studded leather, ring of free action, cloak of protection

Bonus Actions: dash, disengage, hide, feint (advantage on next attack), second wind, Perception and Investigation checks, Insightful Fighting
Reactions: Uncanny Dodge, Brace

I have lots of options competing for bonus actions, but I figure each are situational enough. Use insightful fighting in first round (or even before combat starts), use Feinting Attack on other enemies without insightful fighting, while maintaining the ability to stay mobile and hide, as needed. Precision attack for low attack rolls, and Brace to double sneak attack per round. Halfing Lucky plus the Lucky feat can also turn fails into successes consistently.


Maneuvers: I have also considered Riposte (reaction attack when enemy misses with melee attack) in addition to Brace (reaction attack when enemy approaches). Would it be worth replacing Precision Attack or Feinting Attack, or even picking up the Martial Adept feat? Tactical Assessment (bonus to Investigation, History, Insight) would also be nice, but only if I can decide "after making the roll."

I like Lucky for both personality as well as shear power. Is it worth the trade for +2 Wis, or another feat? Also, is the 10th level ASI a good time to take it?

Finally, I'm curious on thoughts for multiclassing order. Definitely starting as rogue, but when should I take the next levels of fighter? I feel like the fighter abilities are meant to bolster sneak attack, so perhaps three levels of rogue first, then all three levels of fighter, then back to rogue. But I'm not sure if I'm missing any other synergies.

Any other advice? Thanks!


I'v played Human variant - rogue 1, wizard 4 detective. Rolled stats, so started with 18 Inteligence, 16 dex, 16. wis.... So I'v take 2 feats - observant and keen mind - can read lips, remember everything. Expertize in Investigation and Arcana (can be Perception as well).. You will have so high passive perception, that GM have to tell you everything when you come in to place of crime :D

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