"Great Detective" (Sherlock Holmes-ish) PC?

[2D8HP]

I'm reading a Fantasy trilogy that has a"Great Detective" (Sherlock Holmes-ish) character and I'm wondering how to do a 5e PC that resembles such a character.

Investigation skill of course, proficiency in a disguise kit, maybe the Tavern Brawler Feat, then what?

What background, skills etc would best match the character?

[King539]

Mystic, Rogue or Bard for investigation expertise.

[Kileonhardt]

I'm reading a Fantasy trilogy that has a"Great Detective" (Sherlock Holmes-ish) character and I'm wondering how to do a 5e PC that resembles such a character.

Investigation skill of course, proficiency in a disguise kit, maybe the Tavern Brawler Feat, then what?

What background, skills etc would best match the character?

Create your own Detective background. Maybe go with Investigation and Perception as skill proficiency, throw in disguise kit for a tool proficiency, an extra language. Stuff like that.

[Lord Il Palazzo]

I'd probably aim for the Inquisitive Rogue archetype from the Gothic Heroes Unearthed Arcana (here (http://dnd.wizards.com/sites/default/files/media/upload/articles/UA%20Gothic%20Characters.pdf)). Not being able to roll less than an 8 (effectively) on Insight checks to tell if you're being lied to and being able to make Perception and Investigation checks as a bonus action feel very Great Detective-y and the Insightful Fighting feature (beat an enemy's Deception check with your Insight check and you can sneak attack them without the usual requirements) reminds me a lot of Holmes' analytical fighting style in the Robert Downey Jr. movies.

The problem with a detective character like Sherlock Holmes or Batman in D&D is that there are too many skills he should have. Investigation, Perception, Insight and Deception for starters, but arguments could be made for Athletics, Persuasion, Intimidation, Stealth, Sleight of Hand and probably others too (like any given Int skill for certain situations with Holmes' habit of picking up odd bits knowledge he thinks will be helpful).

[Specter]

Rogue (Inquisitor)/Bard multiclass. As many skills as you want, up to six of them expertised, and magical support to back it up. Can't go wrong.

[Lord Il Palazzo]

Rogue (Inquisitor)/Bard multiclass. As many skills as you want, up to six of them expertised, and magical support to back it up. Can't go wrong.Good call. A lot of bard spells would be great for an investigative type: Speak with Animals, Comprehend Languages, Disguise Self, Invisibility, Locate Object, Detect Thoughts, Speak with Dead and so on would all be tempting. Plus, if you really wanted a Sherlock Holmes vibe, violin proficiency!

[Beleriphon]

Good call. A lot of bard spells would be great for an investigative type: Speak with Animals, Comprehend Languages, Disguise Self, Invisibility, Locate Object, Detect Thoughts, Speak with Dead and so on would all be tempting. Plus, if you really wanted a Sherlock Holmes vibe, violin proficiency!

Or if one wants to follow Lego Batman's mold, the electric guitar.

[Asmotherion]

A) A custom Backround giving you proficiency in Investigation and Insight together with thief's tools or some other toolset that would be theme-appropriate. This is optional, just here for more fluff.

B) Bard 10/Rogue 8/Warlock 2 Multiclass for expertese in a total of 8 skills. Investigation and Insight should be your first two picks, follower by Perception and Stealth. Sleight of Hand (for picking evidance without being noticed) and Intimidation (for interogations) are nice expertese choices to progress, as well as Deception and Persuation for investigating RP. My personal flavor (as a Warlock fan) would be a couple warlock levels for Mask of many faces (as well as an optional Agonising Blast), to be able to instant-disguise self at-will, which can be a very good ace in your investigations, as well as swiching one of your experteese for performance to "act in character" when pretending to be someone else. As for leveling, I would start with Rogue 1/Warlock 2/Rogue 5/Bard 10. Optionally, after Bard 3 (or Bard 6 for magical secrets) swich back to Rogue to trade 1 of your expertese for additional Sneak Attack Damage. Option 2 can also be spent on Warlock for more invocations, as some of the at-will ones can be very precious to a detective, such as Beast Speach, Devil's Sight, Eldritch Sight, Eyes of the Rune Keeper, Misty Visions, Whispers of the Grave and Voice of the Chain Master (for Pact of the Chain, a really good investment for an invisible familiar spy).

C) Archetypes: Old One Patron seems to fit better than Fiend as a theme and as an ability (telepathy can give a lot of interesting RP). Archfey too, but I personally favor the Old One. Bard is better with College of Lore, as Magical Secrets can give you great options, be it for more investigation flavor or more utility. All Rogue archetypes fit here, with a bit of re-flavoring. I like Arcane Trickster the most, for his invisible Mage Hand, as I can think of more than one RP uses for it. Thief can be re-flavored as a detective who works/used to work undercover and has connections with criminal circuits, wile Assasin can be re-flavored as either a Dexter-like Detective/Sociopath who kills only the ones he believes that deserve it, or as a master of infiltration/spy-like character who also happens to be a master marksman/hitman.

D) Race: Half-Elf for extra Skill proficiencies to apply your Experteese on. Otherwise any race can make it, as long as it gives relative AS bonuses (Intelligence>Wisdom>Dexterity>Charisma as a guidline, but don't focus too much on priorities, they are just there as a gross guidline).

[Biggstick]

I know you didn't ask for a multiclass character, but I built a character with a similar concept you're going for. He was a Human Variant who took Inspiring Leader as his starting feat (you can grab whatever you feel fits the flavor most, but it was great to have on a primary Rogue class). At the time, I had rolled stats as well, so I was able to grab the Observant feat as well, which did wonders for my passive perception score. If you can fit that in (which you can pretty easily on a primary Rogue), it makes you even better at spotting things.

Human Swashbuckler Rogue (City Watch: Investigator background)
Skills: Investigation, Insight, Perception, Stealth, Persuasion, Acrobatics, and History.
Expertise: Investigation and Perception (at Rogue 6, grab expertise in Persuasion and Insight).
Stats: 8 Str, 15(+1) Dex, 14 Con, 10 Int, 12 Wis, 13(+1) Cha.

Leveling progression.
PC1: Rogue 1
PC2: Rogue 2
PC3: Rogue 3 (Swashbuckler)
PC4: Warlock 1
PC5: Warlock 2

At this point, you're at a decision point for the character. You can go the one more level of Warlock to grab a pact, or just hang out at level 2 Warlock. I would suggest at least two Warlock levels for the invocations. Invocations I used and would encourage you to use are the Devil's Sight (dark vision for humans yay!), Eldritch Sight (Detect Magic at will for an Investigator is pretty awesome), or the Disguise Self at will Invocation. Any combination of these three are great on this type of character. I'd also suggest grabbing Booming Blade as one of your cantrips, as it does wonders for the damage output of a Swashbuckling Rogue.
If you decide to not multiclass, I could just as easily recommend going straight Swashbuckler Rogue. Throw that Expertise in Investigation/Perception at level 1, and then Insight + one other at level 6. Grab History as a skill as well to account for knowledge skills. I'd also say take a look at SCAG's City Watch background or the PHB's Sage background for features that appeal to your character.

[Autocon]

I would probably go with a custom background, but if you were looking for official backgrounds, SCAG City Watch variant Investigator would work.

[Arkhios]

With inquisitive rogue/lore bard combo, pick variant human and start with rogue and skilled feat. If there's a skill you're not proficient with, maybe you're not meant to be. And even then you'd add half of your proficiency in it!

Quick math (iirc):

Rogue: 4 skills
Skilled: 3 skills
Human: 1 skill
Bard multiclass: 1 skill
Lore bard: 3 skills
Background: 2 skills

If I didn't miss anything, that's a total of 14 skill proficiencies, nearly half of which you'd have expertise with. (There are a total of 18 skills, and you'd handle quite a big majority of them really well)

[Naanomi]

With inquisitive rogue/lore bard combo, pick variant human and start with rogue and skilled feat. If there's a skill you're not proficient with, maybe you're not meant to be. And even then you'd add half of your proficiency in it!

Quick math (iirc):

Rogue: 4 skills
Skilled: 3 skills
Human: 1 skill
Bard multiclass: 1 skill
Lore bard: 3 skills
Background: 2 skills

If I didn't miss anything, that's a total of 14 skill proficiencies, nearly half of which you'd have expertise with. (There are a total of 18 skills, and you'd handle quite a big majority of them really well)
Tack on Knowledge Cleric (two more, with expertise, and medium armor/shield proficiency)
Then Warlock (two more through invocation, and Eldritch Blast covering all your combat needs)

[Arkhios]

Tack on Knowledge Cleric (two more, with expertise, and medium armor/shield proficiency)
Then Warlock (two more through invocation, and Eldritch Blast covering all your combat needs)

That would work, but then again Eldritch Blast isn't really a Sherlock Holmesy thing. If, however you'd be doing a Robert Downey Jr mock up mix between Sherlock Holmes and Iron Man, then it might work better within concept :P

Anyway, here's a more detailed "plan" for the earlier idea I posted:

make variant human.
Start with Inquisitive Rogue 6 (four expertises), and take the Skilled Feat as your variant Human bonus feat.
Then, turn to Lore Bard for 10 levels (not too shabby another four expertises, and 4 out of class spells up to 5th level)
After that, either turn back for Rogue and continue to 10th level as is, or take two levels in Knowledge Cleric (yet another two expertises!), which is really fitting for the concept mind you, and either take 2 more levels in rogue (if you need that ASI) or in Warlock if you really absolutely want to be proficient with ALL skills there are :P~

In the end you'll be at 16 or 18 proficient skills out of all 18 skills available, and you'll have expertise with a whopping 10 of them. AND you won't even be that bad in combat, either.

With Point Buy and 27 points, you could start with following

Str 8, Dex 16, Con 12, Int 12, Wis 13, Cha 14; putting your human ability score improvements into Dexterity and Charisma. First ASI to get Resilient Wisdom, because a Sherlock Holmes would want decent mental abilities through and through.

[Pronounceable]

Ranger.
https://i.ytimg.com/vi/FUkTRV5EjSA/maxresdefault.jpg

[Gignere]

Playing one right now using divination wizard I even reskinned portent to be me using his intellect and logic to deduce the most likely outcome instead of seeing the future.

[Breashios]

All of this actually depends on you being successful in your observation and deduction. The game offers many tools illustrated in numerous examples above of how to improve your observation. Divination is the only one I see really helping with the deduction side. Otherwise it is all on you, the player, being able to put the clues together for your character to speak the correct conclusion.

At the beginning of the campaign I am currently running one player mentioned his character was a combination of blah, blah, blah and Sherlock Holmes. I thought little of it. He rambles a lot in the game, often off topic, and is not seen to be much of a sharp wit. However, he plays reasonably well and despite sometimes not being aware when it is his turn to act, participates fully in the roleplaying portions. Much to my surprise his character blurted out one conclusion after another that were spot on, though how spot on he was usually wasn't proven to the party until two or three sessions later.

Now I do include subtle clues throughout my games that allow players to do this, but his ability became uncanny for a while. Since we started the campaign with an adventure that I had written, I know he did not have secret access to the adventure material.

Now that we are in Princes of the Apocalypse, his deduction hasn't been as spot on, but he has already earned the reputation and still has some good insight from time to time. So it didn't take too much of a build to accomplish this, just paying attention and following the clues I guess.

His build: Straight Evoker Wizard, Noble background with History and Investigation, Arcana and Persuasion.