Your character will have 1 turn to set up, and then make 1 skill check for each skill.

Your total score is the sum of all results for the ability checks. (Recommended to use the average of the rolls to avoid RNG, but if you like gambling you can roll all the dice yourself)

Rules:

1. One level 20 character
2. Max 6 magic items (any rarity)
3. No d100s
4. No blessings, charms, or the like
5. No other creatures unless they are from a feature or magic item
6. If it can be on your dnd beyond character sheet, it's probably legal
7. First party content is legal
8. No 3rd party content
9. Either only 2024 or only 2014
10. You decide the DC for the skill checks (some abilities rely on success or failure)
11. No wish (too subjective)

Feel free to ask for any other rules clarifications.

Let's see how big the numbers can get.

(Recommended to use the average of the rolls to avoid RNG, but if you like gambling you can roll all the dice yourself)

If this is about Skill bonus, then all abilities need to be the same, and for ease make them all 10 (or 8) across the board.  No beginner ability score increase or set it so all have the same +2/+1 or +1/+1/+1.

Set what books are valid,  If some has so new 3rd party book, I would not be able to compete. Ergo say what is valid and what is not.  2014 creations will probably be different from 2024 rules. 

Example build:

2024 rules

Changeling Rogue (Soulknife) 20

8/12/8/20/20/16

Boon of skill and mark of finding

Ioun stone of mastery, ioun stone of leadership, luck stone, tome of clear thought x3 (probably better options)

Setup round:

Action shapeshift (adv on cha checks)

You know what, I will roll everything

18 checks

13d20(min 10)+4d20(min 10, adv)+20(stroke of luck)+12d12(Psi-bolstered knack)+2d4(Mark of finding)+7x18(PB)+7x6(expertises)+18(luck stone)-1(str)+1x3(dex)+8x5(int)+5x5(wis)+4x4(CHA)

for a total of 613

I have no idea if that's good or not, but let's see what other people can come up with.

This could be really complicated because you are allowing 6 magic items.  But Artificers can also make some and I'm pretty sure that shouldn't/wouldn't count.

Also I am curious if we are doing this in combat round style or if its out of combat, because action economy could come into play.

I can't do it yet but I will soon. 

It's really pretty easy:

Rules: 2024
Species: Shifter - Wildhunt
BA Shift on Turn 1 for Adv on Wis
Action on Turn 1: cast Enhance Ability on self for Adv on Int ---> Candle of Invocation for Adv on all skill checks

Background Feat: Skilled
Proficiencies: Animal Handling, Intimidation, Persuasion
Background Skills: Investigation, Perception

Level 1: Rogue. ASIs: 9, 13, 8, 16 (14+2), 16 (15+1), 13 
Proficiencies: Acrobatics, Athletics, Deception, Insight
Expertise: Acrobatic, Athletics

Lore-Bard 15: 
Proficiencies: Medicine, Performance, Sleight of Hand
Expertise: Deception, Insight, Sleight of Hand, Performance
Peerless Skill : set DC to 60, so can add 1d12 to every skill check.
Feat 4th level : Skilled
Proficiencies: Stealth, Survival, Religion
Feat 8th level: Skilled
Proficiencies: Nature, History, Arcana
Feat 12th level: +2 Wis

Wizard 2:
Expertise: Medicine

Cleric 1: Thaumaturge +Wis to Arcana & Religion

Level 20:
ASIs: 9 (-1), 13 (+1), 8(-1), 16(+3), 18(+4), 13(+1) 

Proficient: All skills (+7) ---> Ioun Stone of Mastery for +1 Proficiency Bonus

Expertise: Medicine, Deception, Insight, Sleight of Hand, Performance, Acrobatics, Athletics
Extra: +1d12 to all checks, +4 (Wis) to Arcana & Religion
----> Stone of Good Luck x3 : +3 all skills

Final Skill bonuses:

Acrobatics (Ex): +18
Animal Handling : +14
Arcana  : +17
Athletics (Ex): +16
Deception (Ex): +18
History : +17
Insight (Ex): +21
Intimidation : +11
Medicine (Ex): +21
Nature : +13
Perception : +14
Performance (Ex): +18
Persuasion : +11
Religion : +17
Sleight of Hand (Ex): +23 -------> Gloves of Thievery for +5
Stealth : +11
Survival : +14

Total Modifiers = 223

Rolling with Adv = average of 13.8; average of 1d12 = 6.5

Expected Total = 18*13.8+18*6.5 + 223 = 583

Quote from Agilemind >>

Sleight of Hand (Ex): +23 -------> Gloves of Thievery for +5

 I think another luckstone would be better than gloves of theivery

I feel like any build that does not include simulacrum is going to fall short.

Human Soul Knife 3 - Lore Bard 13 - Warlock 2 - Artificer 2

This might be the GOAT skill monkey build.  I have not built it yet, but I can visualize it.

I do not have time to crunch numbers today.  But I wanted to share the concept first.

Quote from packman767 >>

I feel like any build that does not include simulacrum is going to fall short.

 

 I don't see how simulacrum could be useful. It making skill checks isn't going to contribute to your score, help only gives 1 check advantage and a familiar could do it, and you don't even have 12 hours to cast it in the first place. If you have some other strategy based on simulacrum, feel free to enlighten me.

Quote from Whatstray >>

Quote from packman767 >>

I feel like any build that does not include simulacrum is going to fall short.

 

 I don't see how simulacrum could be useful. It making skill checks isn't going to contribute to your score, help only gives 1 check advantage and a familiar could do it, and you don't even have 12 hours to cast it in the first place. If you have some other strategy based on simulacrum, feel free to enlighten me.

 Well I mean if you can pull off a Simulacrum with wish somehow its instantaneous.

So a Lore Bard 17, Peace Cleric 3 could cast wish to cast semulacrum and then Emboldening Bond to add a d4 to all ability checks…. and the simulacrum could cast Wish to Reshape Reality and turn every side of the player’s d20 into a natural 20 for 1 hour.

You know…. 🧀🧀the cheese🧀🧀

The problem is that the simulacrum has to wish for that, and the concept of a "natural 20" isn't a thing, at least from the character's perspectives.

Quote from Whatstray >>

The problem is that the simulacrum has to wish for that, and the concept of a "natural 20" isn't a thing, at least from the character's perspectives.

 It would be phrased like, “Reshape reality so that I am successful in all of my skilled endeavors for 1 hour….. “ like that potion that Harry Potter drinks in Book/Film 3.

I think this absolutely could be granted by the Wish spell.  And the DM tradeoff might be to fail everything the following hour.  But its the price we pay to win the build competition.  LOL

Now for an actual GOAT build I would only need Bard 13 because I could just take the 12 hours to build the snow man like its the winter olympics, and then still get all my warlock and artificer goodies too.

Sure, now the DC for all the checks is 1.

Wish is incredibly subjective, so I might ban uses other than replicating a spell or one of the other listed uses

Quote from Whatstray >>

Wish is incredibly subjective, so I might ban uses other than replicating a spell or one of the other listed uses

 In the spirit of what you are trying to do I would ban the wish spell AND simulacrum because then we’ll be forced to crunch numbers.

But with my above mentioned trick, I am hitting about 22.5 on every skill before I factor in proficiency and expertise bonuses and gear.  The minimum score for a Bard 17, Peace Cleric 3 setup as I described would be about 

18 * 22.5 = 405 before any gear, proficiencies, expertise, etc.  This is just natural 20 + Emboldening Bond.

If I casually add in proficiencies it would be something like **(numbers don't show up when I save but.... trust me bro):

So without any magical items I am at 174 + 504 (no RNG here) = 678.  This is without magical items.  Just add whatever 6 item bonuses you used to get my score higher and that's my final score.

 I opted for the "Slap wisdom on everything" approach. The cleric's divine order (thaumagurge) lets you add your wisdom modifier to arcana and religion. The fey wanderer ranger's otherworldly glamour lets you add your wisdom modifier to charisma checks.

You could add the druid's primal order (magician) too, but that would only add one more skill in this case; It ended up not being as useful as bard at the end.

My build went as:

• Point Buy: 8 str, 13 dex, 8 con, 12 int, 15 wis, 15 cha.
• Race: Shifter (wildhunt) for a skill and the advantage on wisdom skills.
• Background: Scribe. 2 wis/1 dex, Skilled. 5 skills there.
• Starting class: Rogue, for 4 skills.
• 6 levels of Rogue (Soul Knife). 4x expertise, and Psi Bolstered Knack to add a d8 to a failed skill roll (6 psi dice available, not expended unless it helps).
• 3 levels of Cleric (Knowledge). 2 skills, 2x expertise, and adding wisdom to arcana and religion.
• 9 levels of Ranger (Fey Wanderer). 2 skills (1 base, 1 subclass), 4x expertise, and adding wisdom to charisma checks.
• 2 levels of Bard, for 2x expertise and Jack of All Trades (half proficiency in the few untrained skills remaining)
• ASI / Feats: 3 are available with this build. Skill Expert (1 skill, 1 expertise, wisdom), Observant (1 expertise, wisdom), and +1/1 wis/cha.
• Magic Items: 5x Tome of Understanding (permanent +2 wis each, to bring Wisdom to 30), and a Stone of Luck for +1 all skills.

So that's proficiency in all but 2 skills, and expertise in 12 of them, with a monstrous wisdom bonus being added on top of 6 skills it doesn't normally go on.This guy has an average of +18 on all rolls, with his flat bonuses totaling 324.

For the preparation round, take an Action to cast Enhance Ability (int), and Bonus Action to shift. That gives advantage on 10 skills. A d20 roll averages 10.5 normally, or 13.8 with advantage. So, the base rolls on 18 skills ends up being (10 advantages * 13.8) + (8 straight rolls * 10.5) = 222 from the d20s.

The Soulknife rogue has Psi Bolstered Knack, which lets you add your psi dice to a failed roll, and you keep if it still doesn't help. I think it's kinda cheesy to say "Oh, the DC is impossibly high, so let's apply that to all 18 skills and still fail", but everyone else is doing it. So, that's a +4.5 average added to each roll. (81 to the total).

All together, that is: 222 on the d20s + 324 in static bonuses + 81 from psi dice, for a total of 624.

Warlock spend all your invications on lessons of first ones. Take the skilled origin feat over and over.