What class pick to be an aweasome skill monkey?

[Aleister VII]

Okay I'm aiming to make a skill monkey with many proficiencies and expertise, I need insight, perception, deception, persuasion, performance and investigation, any other skill is also welcomed but those are the main ones, I'll need high charisma and wisdom to make most of them work, the races will most likely be half elf but I'm not sure about what class, maybe bard or rouge, what do you think?

the idea is be a very perceptive detective that is also an expert in the humanoid behavior, it will also have the charlatan background for thematic reasons.

[Laserlight]

Okay I'm aiming to make a skill monkey with many proficiencies and expertise, I need insight, perception, deception, persuasion, performance and investigation, any other skill is also welcomed but those are the main ones, I'll need high charisma and wisdom to make most of them work, the races will most likely be half elf but I'm not sure about what class, maybe bard or rouge, what do you think?


Yes, a rogue or bard would make a good skill monkey.

[lperkins2]

Bard tends to do the best. Expertise + jack of all trades is pretty powerful just in terms of skill proficiencies. Then you add in utility spells (feather fall, enhance ability, et cetera) and it gets amazingly good. Rogues win out in the utility-but-still-do-damage area, but bards are generally the best at pure utility.

[Lunali]

If you're going to be 11+, rogue, reliable talent is a game changer for a skill monkey.

If you wanted to go all in, half elf scout rouge 11/lore bard 3, skilled and prodigy feats for proficiency in everything, expertise in half of them (or thief's tools) and never rolling under 10 on anything you're proficient in.

[Snowbluff]

If you're going to be 11+, rogue, reliable talent is a game changer for a skill monkey.

If you wanted to go all in, half elf scout rouge 11/lore bard 3, skilled and prodigy feats for proficiency in everything, expertise in half of them (or thief's tools) and never rolling under 10 on anything you're proficient in.

Knowledge Cleric gives you prof and expertise in 2 knowledge skills, and I'd take Arcane Trickster for level 10 anyway. Combined with Guidance it would be a good dip. Also, IMO you should bring Bard to at least 5 for short rest inspiration recovery.

[Banana3lf]

Id suggest a weird yet beneficial multiclass.
Build to lvl 9 and go wherever you see fit after that
Lore bard 3/great old one tome lock 3/swashbuckler rogue 3 variant human with observer feat. Cha high, dex high, wisdom as high as you can.

Your passive perception and ability to read lips will be astounding as a combo with detect thoughts and telepathy. Swashbuckler for booming blade and sneak attack with rapier and no opportunity attacks for some pretty consistant dmg. Lore bard 3 for jack of all trades and extra skills and inspiration for your fellows.
After that you could go many directions but warlock with mask of many faces and eventually caping at 20 with thralls for the 14th level feature is very nice.

[Lunali]

Knowledge Cleric gives you prof and expertise in 2 knowledge skills, and I'd take Arcane Trickster for level 10 anyway. Combined with Guidance it would be a good dip. Also, IMO you should bring Bard to at least 5 for short rest inspiration recovery.

Knowledge cleric is a decent way to make up for choosing a different rogue subclass if you want, though it does mean another attribute you need.

As for increasing bard, the build I suggested is for lvl 14, so there's room to level however you want. If I were doing it though and was actually expecting to play at lvl 20 for any length of time, I'd probably go full scout rogue for two sneak attacks per turn.

[Banana3lf]

Id suggest a weird yet beneficial multiclass.
Build to lvl 9 and go wherever you see fit after that
Lore bard 3/great old one tome lock 3/swashbuckler rogue 3 variant human with observer feat. Cha high, dex high, wisdom as high as you can.

Your passive perception and ability to read lips will be astounding as a combo with detect thoughts and telepathy. Swashbuckler for booming blade and sneak attack with rapier and no opportunity attacks for some pretty consistant dmg. Lore bard 3 for jack of all trades and extra skills and inspiration for your fellows.
After that you could go many directions but warlock with mask of many faces and eventually caping at 20 with thralls for the 14th level feature is very nice.

I should mention the draw here is proficiency in 11 skills. It not all out skill monkey but does capitalize on what you have.

[CTurbo]

Tabaxi Swashbuckler Rogue 11/Swords or Valor Bard 9


Half-Elf Lore Bard 3, Knowledge Cleric 1, Scout 11, Ranger 1, Warlock Tome 3 with the skilled feat of course

[Greywander]

I'd just like to point out the interaction between Reliable Talent and Jack of All Trades. With these two features, you can never roll less than a 10 on any ability check, including ones you can't normally get proficiency in, like initiative rolls (which are DEX checks).

Aside from that, I can also recommend half-elf, with a mix of Lore bard (for JoAT and more skills), rogue (for Reliable Talent), and Knowledge cleric (for Guidance and additional skills w/ Expertise). This alone should give you proficiency in 12 skills with Expertise in 8 of those. Rogue 11 / Lore bard 3 / Knowledge cleric 1 is a good base to build off of. I'd second going Arcane Trickster for the magic. I'd also try to pick up Ritual Caster (wizard) if you don't have a wizard in the party so you have more tricks up your sleeve. Another good addition is 3 levels of warlock, Great Old One patron for telepathy, Chain pact for an invisible, flying pet.

Let's lay out some of your options in a way that's easier to parse (this assumes you start as a rogue and then multiclass):

(Race: half-elf, 2 skills, 3 languages, +4 to ability scores, Darkvision)
(Background: 2 skills, 2 languages or tools)

Rogue: 11th level, 4 skills, 4 expertise, 1 tool, Reliable Talent
Scout: +2 skills, +2 expertise
Arcane Trickster: +4 cantrips, 2nd level wizard spells
Mastermind: +3 tools, +2 languages, help as a bonus action from 30 feet away

Bard: 3rd level, 1 skill, 2 expertise, 1 tool, 2 cantrips, 2nd level bard spells, Jack of All Trades
Lore: +3 skills

Cleric: 1st level, medium armor, shields, 3 cantrips, 1st level cleric spells
Knowledge: +2 skills, +2 expertise, +2 languages
Arcana: +1 skill, +2 cantrips

Warlock: 3rd level, 2nd level warlock spells, 2 invocations
Patron - Great Old One: one-way telepathy
Patron - Celestial: +2 cantrips
Patron - Hexblade: use CHA for weapon
Pact - Chain: invisible flying familiar (I can't overstate how useful this is), access to Voice of the Chain Master
Pact - Tome: +3 cantrips, access to Book of Ancient Secrets (only up to 2nd level spells, though)

This gives you two more levels to choose from. I'd suggest either Diviner wizard 2 for Portent, or bumping bard and warlock up to 4th level for two feats and two cantrips. Keep in mind you'll only get 3 ASIs otherwise, so this would bring you up to 5. This build is a bit MAD, so you should be happy with mostly 14s and 16s in your ability scores (and you'll likely need to dump STR and CON), and don't expect to push any score to 20. Expertise and Reliable Talent help to offset these slightly lower ability scores.

The reason I'm featuring magic so prominently is that cantrips tend to be more useful than skill proficiencies, particularly if you already have JoAT and Reliable Talent. I'm assuming you're wanting to build a character that can handle out-of-combat puzzles and social encounters, for which cantrips can be very useful. And since your character may not be well suited for combat, I included a few options, such as the Mastermind and Hexblade, that can give you something to do in combat.

As for what order to take class levels in, it's up to you. It's temping to dip early when you can gain so much for just a few levels, but Reliable Talent is really that good, and a straight rogue is an excellent skill monkey anyway.

[Unoriginal]

There's also the Prodigy feat, to get Expertise.

[Exocist]

Half-Elf Rogue 1/Cleric (Knowledge) 1/Lore Bard 3/Warlock (Any) 2/Rogue +10

Skills = 2 (Half-Elf) + 2 (Background) + 4 (Rogue) + 2 (Knowledge Cleric) + 4 (1 from Bard multiclass, 3 from Lore Bard) + 2 (Warlock, Beguiling Influence invocation) + 3 (Skilled) = All the skills in the game, with 11 levels in Rogue you can get reliable talent on all of them.

Only kidding - A lore bard is probably the best fit for you, they're Charisma-focused (Rogue is more dexterity-focused), have a lot of skills (2 from background + 3 from class + 3 from subclass for 8) and are generally very effective as support characters (The bard spell list is pretty support-y already, but Cutting Words is great at keeping your party alive for minimal resource investment and that additional Magical Secrets is invaluable). If you want the means to do damage, you can multiclass into Warlock (I suggest Hexblade) for 2 or 3 levels to pick up Eldritch Blast (+ Agonising Blast) as a means of consistent damage without investing resources. Your other invocation can be Mask of Many Faces (for disguising), Misty Visions (for deluding people) or Beguiling Influence (more skills).

[Contrast]

I'd just like to point out the interaction between Reliable Talent and Jack of All Trades. With these two features, you can never roll less than a 10 on any ability check, including ones you can't normally get proficiency in, like initiative rolls (which are DEX checks).


I should point out that Sage Advice says it doesn't work like that (https://www.sageadvice.eu/2017/10/15/how-would-reliable-talent-work-with-a-roguebard-and-their-jack-of-all-trades/).

[Aaron Underhand]

I would personally go Lore Bard, with just a two level dip into knowledge cleric.

You are the bard skill monkey, and pick up Enhance Ability

Cleric gives you guidance and bless

Knowledge cleric gives you the expertise, plus

** Channel Divinity to become proficient in any skill for 10 minutes **

[Greywander]

I should point out that Sage Advice says it doesn't work like that (https://www.sageadvice.eu/2017/10/15/how-would-reliable-talent-work-with-a-roguebard-and-their-jack-of-all-trades/).
That's not what the Compendium (https://media.wizards.com/2017/dnd/downloads/SA-Compendium.pdf) says. Look under "rogue", third from the bottom (sorcerer) on page 5. They work together.

With how much the devs waffle back and forth on issues like these, or outright contradict each other, I'm not surprised that so many people disregard anything JC and MM say unless it's written in a rulebook.

[Aleister VII]

Interesting... I think I'll go for lore bard and take a dip into warlock to not suck in battle, most likely with the GOO patron for the telepathy or the celestial to get some cleric spells, does it's expanded spell list include guidance? I can't quite remember x.x

Anyways, the warlock level will at most be just 2 to get agonizing blast and another invocation, after that I'll consider a dip in rogue but I don't think that the campaign I'm going to play will last that long x.x

As for feat observant sounds amazing for the PC's concept and I'm also considering prodigy for extra skills and expertise.

I however haven't decided if I should pick half elf or V. Human, the former nets me more skills and charisma but the later can give me prodigy from the start and that means expertise.
Furthermore I can ignore the lack of darkvision as I'll just take the devil's eyes invocation when I take my warlock dip.

Also... what spells are really worth taking with magical secrets? I'm thinking in a paladin or ranger spells as you can't get them with magic initiate and are almost class exclusive and even so they come online too late IMO.

[Greywander]

Interesting... I think I'll go for lore bard and take a dip into warlock to not suck in battle, most likely with the GOO patron for the telepathy or the celestial to get some cleric spells, does it's expanded spell list include guidance? I can't quite remember x.x
Cleric cantrips aren't added to your spell list, but you do get Light and Sacred Flame for free. If you're getting Agonizing Blast, Sacred Flame will only be situationally useful (you can use it in melee without penalty, some enemies like vampires need radiant damage to stop their regeneration, it bypasses cover, etc.).


Anyways, the warlock level will at most be just 2 to get agonizing blast and another invocation, after that I'll consider a dip in rogue but I don't think that the campaign I'm going to play will last that long x.x
Do be aware that multiclassing doesn't get you the same proficiencies as if you started in that class. For example, multiclassing into fighter doesn't give you heavy armor proficiency. In the case of rogues, you'll start with one more skill proficiency if you start as a rogue versus multiclassing into rogue later on. Likewise, if you start as a bard you get proficiency with 3 instruments, but only 1 if you multiclass into bard later. Skills are generally more important than tools (like instruments), and tool proficiencies can be learned during downtime.

If the campaign isn't going to last that long, then you're probably better off staying single-classed. Lore bard is a solid pick in this case, as you get JoAT early, you get a bunch of skills, in addition to solid support magic. Vicious Mockery will be your go-to attack, and will help reduce the damage your allies take. Make sure to target the biggest, baddest, hardest hitting monster so that making them miss on an attack will save the most HP, but also be careful of enemies that might have a good Wisdom save. As a bard, you are a support class, not a tank or damage dealer, but good support can multiply your party's effectiveness.


As for feat observant sounds amazing for the PC's concept and I'm also considering prodigy for extra skills and expertise.
With Observant, expertise in Perception or Investigation, and a WIS or INT of 16, you can get your passive checks up to 30 (at 17th+ level). You'll see everything without even looking for it.


I however haven't decided if I should pick half elf or V. Human, the former nets me more skills and charisma but the later can give me prodigy from the start and that means expertise.
Furthermore I can ignore the lack of darkvision as I'll just take the devil's eyes invocation when I take my warlock dip.
Half-elf is better in the long run, as the +2 to CHA is equivalent to a feat/ASI. If you never intended to spend an ASI on CHA, then V human might be better. It also depends a lot on what feat you wanted to get, as some of them (e.g. Polearm Master, Heavy Armor Master) can be massively effective at low levels but drop off a bit later on, while others (e.g. Resilient) don't become significant until higher levels.


Also... what spells are really worth taking with magical secrets? I'm thinking in a paladin or ranger spells as you can't get them with magic initiate and are almost class exclusive and even so they come online too late IMO.
Fireball is a good one, and even as a support character it can be nice to have a few tricks up your sleeve if you get into a sticky situation. In general, though, I'd look for control spells (Wall of Fire, Darkness, Sleet Storm), support spells (Bless, Shield of Faith, Enlarge/Reduce), or utility spells (Spider Climb, Fly, Fabricate).

What's the composition of your party?


the idea is be a very perceptive detective that is also an expert in the humanoid behavior, it will also have the charlatan background for thematic reasons.
If this is your concept, rogue would probably fit best, either Inquisitive or Mastermind. That said, any concept can be played with any class, so don't feel like you need to be one class or another for your concept to work. A druid detective, for example, could be an interesting concept!

Remember, you don't have to optimize. 5e is pretty good about making even unoptimized builds playable. Just make sure you're having fun and don't worry too much about the mechanics (unless you have a killer DM).