There are a lot of discussions out there about character optimization, but I got curious about how much I could optimize a character based on skills. Most normal builds get a pretty limited selection of skills, so you have to go to some weird lengths to really get a big array of skills.
Here are all of the possible sources of skill/tool proficiencies that I’ve been able to find:
Dwarf – Choice of Smith’s Tools, Brewer’s Supplies, or Mason’s Tools.
Elf (High) – Perception.
Human (Variant) – One skill of your choice. One feat of your choice (see below).
Gnome (Rock) – Expertise in some History checks.
Half-Elf – Two skills of your choice.
Half-Orc – Intimidation.
Barbarian – Two from Animal Handling, Athletics, Intimidation, Nature, Perception, and Survival.
Bard (Lore) – Any three skills, any three musical instruments. College of Lore (any 3 skills) at Level 3. Expertise at levels 3 and 10.
Cleric (Knowledge) – Two from History, Insight, Medicine, Persuasion, and Religion. Two languages of your choice. Two from Arcana, History, Nature, or Religion (with expertise).
Druid – Herbalism Kit. Two from Arcana, Animal Handling, Insight, Medicine, Nature, Perception, Religion, and Survival.
Fighter – Two from Acrobatics, Animal Handling, Athletics, History, Insight, Intimidation, Perception, and Survival. Champion gets Remarkable Athlete and 7. Battle Master gets Student of War at 3.
Monk – Two from Acrobatics, Athletics, History, Insight, Religion, and Stealth. One artisan’s tools or musical instrument.
Paladin – Two from Athletics, Insight, Intimidation, MEdicine, Persuasion, and Religion.
Ranger – Three from Animal Handling, Athletics, Insight, Investigation, Nature, Perception, Stealth, and Survival.
Rogue (Assassin)– Four from Acrobatics, Athletics, Deception, Insight, Intimidation, Investigation, Perception, Performance, Persuasion, Sleight of Hand, Stealth. Thieves Tools. Expertise at 1st and 6th levels. Poisoner’s kit and disguise kit at 3rd level.
Sorcerer – Two from Arcana, Deception, Insight, Intimidation, Persuasion, and Religion.
Warlock – Two from Arcana, Deception, History, Intimidation, Investigation, Nature, and Religion.
Wizard – Two from Arcana, History, Insight, Investigation, Medicine, and Religion.
Most classes don’t grant you additional skill/tool proficiencies when you multiclass into them. These are the few that do.
Bard – One skill of your choice. One musical instrument of your choice.
Ranger – One skill from the class’s skill list.
Rogue – One skill from the class’s skill list. Thieves tools.
Cleric (Knowledge) – You don’t get any skills for multiclassing into Cleric, but if you choose the Knowledge domain you still get your choice of two from Arcana, History, Nature, or Religion (with expertise) as a domain feature.
All the backgrounds are designed to give you a combination of four languages, tool proficiencies, and skill proficiencies. Backgrounds with no languages will provide more skill proficiencies.
Acolyte – Two languages. Insight, Religion.
Charlatan – Deception, Slight of Hand. Disguise Kit, Forgery Kit.
Criminal – Deception, Stealth. One gaming set, thieves tools.
Entertainer – Acrobatics, Performance. Disguise Kit, one musical instrument.
Folk Hero – Animal Handling, Survival. One artisan’s tools, Vehicles (Land).
Guild Artisan – Insight, Persuasion. One artisan’s tools. One language.
Hermit – Medicine, Religion. Herbalism Kit. One language.
Noble – History, Persuasion. One type of gaming set. One language.
Outlander – Athletics, Survival. One musical instrument. One language.
Sage – Arcana, History. Two languages.
Sailor – Athletics, Perception. Navigator’s tools, Vehicles (water).
Soldier – Athletics, Intimidation. One type of gaming set, Vehicles (land).
Urchin – Sleight of Hand, Stealth. Disguise Kit, Thieves’ Tools.
Many feats give you circumstantial bonuses to certain skill checks, but only one gives you flat-out proficiency in additional skills.
Skilled – Three skills or tools of your choice.
Given all of those options, this is the best skill-master that I’ve been able to come up with. You could probably tweak the state placements and choice of expertise skills depending on your personal preferences, but I think that this is a good starting point for a highly skilled PC.
1st Level – Human (Variant) Rogue 1: Proficiency in 10 skills, Expertise in 2 skills, Proficiency in 3 tools
3rd Level – Human (Variant) Rogue 1, Bard 1, Cleric (Knowledge) 1: Proficiency in 14 skills, Expertise in 4 skills, Proficiency in 3 tools and 1 musical instrument. Access to the Guidance cantrip.
5th Level – Human (Variant) Rogue 1, Bard 3, Cleric (Knowledge) 1: 16 skills, Expertise in 6 skills, Proficiency in 3 tools and 1 musical instrument. Access to the Guidance cantrip.
Here’s an example of the “Most Skilled Man in the World” at Level 5.