What is the sneakiest stealthiest character possible?

[CTurbo]

Level 20, point buy or standard array will be fine

I was thinking levels in Deep Stalker Ranger would be a must, but not sure how many
Also levels in Shadow Monk
Probably some Rogue levels Assassin probably
Maybe even some Warlock levels for obvious reasons

Any other class I may be missing?

I was thinking Lighfoot Halfling or Wood Elf with a 8 Str, 16 Dex, 12 Con, 8 Int, 16 Wis, 14 Char to start

Probably start Monk for unarmored AC. Need 6 levels of Shadow for sure. Probably no more than that. That's 1 ASI which would be +2 Dex
Need at least 3 levels of Ranger for Deep Stalker. 4 for ASI. Already would have extra attack so I don't see any reason to take any more here. would probably go ahead and max Dex if ASI
Rogue is great for several reasons like Expertise, Cunning Action, Evasion, Uncanny Dodge, Sneak Attack, etc,... but how many levels to take? I could see going 7. Probably Assassin for totally ridiculous first rounds, but I could see Arcane Trickster working here too. Just switch Int and Char stats.

Then there is Warlock. Warlock offers a lot of great stuff when it comes to sneaking. It almost makes taking Deep Stalker redundant. I can see taking at least 6 levels here as all 3 of the Patrons' level 6 features would be great for this character. Devil's site is really strong. Devil's site + Darkness spam exists. Mask of the Wild would be great. Misty Visions is great, and One With the Shadows would be AWESOME. Pact of the Chain with an Imp would be perfect for a sneaky character. Can't decide on the Patron though. They all offer something good.


What do you guys think? I'm thinking skip the Deep Stalker and go Shadow Monk, Rogue, and Chain Warlock

 

[Mistwell]

A druid. Wildshaping into the various spiders, which have very high stealth and long range darkvision and spider climbing, is going to be near the top of the list. Pretty easy to start out with a +7 stealth that way. Add to that their spells, like Enhance Ability: Catsgrace which will grant you advantage on those stealth checks, and Pass Without Trace, which will give you a+10 bonus to Dexterity (Stealth), you can't be tracked except by magical means, and you leave behind no tracks or other traces of your passage. You can get a truly obscene stealth check at low levels with this combo.

 

[CTurbo]

A druid. Wildshaping into the various spiders, which have very high stealth and long range darkvision and spider climbing, is going to be near the top of the list. Pretty easy to start out with a +7 stealth that way.

True can't argue that, but that's boring so how about NO Druids wildshaping into insects allowed lol

 

[Nevvur]

Level 20 Wizard. You'll be able to do pretty much everything a sneaky person can, and often without risk of failure - that is, no ability checks because spellcasting is an I WIN button in many situations. Sure, the rogue can scale the walls of the castle and throw a rope down for the party, but it's rainy and slippery and the DC to climb it is 20, while the wizard has fly and dimension door. The shadow monk can sneak ahead and scout out the hallway, or the wizard can send his rat familiar. Or go ethereal, or invisible, send an arcane eye, cast clairvoyance, and so on.

If you've determined you definitely want to play a more traditional stealth character, your proposed build should be fine. I might shift points from Charisma to Constitution for survivability, because it sounds like you're not taking Warlock levels for the types of spells that benefit from high Spell Attack Bonus and Spell Save DC. Unless you're also planning to play the party face and anticipate using social skills like deception and persuasion, that is. (edit: forgot the Charisma requirement for multiclass; was just going to delete this paragraph in the edit, but opted to keep it as a point of order)

That said, if not a level 20 wizard I'd probably just play a thief rogue. It's a solid, easy to play package that does exactly what you want it to do: sneak around. Heavy multiclassing isn't common at my tables, but I have observed that the more abilities a PC has, the more likely the player is to forget some of them. I also generally advise against playing esoteric multiclass builds for high level one-shots because you haven't had time to grow into the character; and perhaps just as importantly, to learn how the DM adjudicates the use of your abilities.

 

[Warmaster Horus]

I'd go with a Wood Elf Rogue with Expertise in Stealth, a Cloak & Boots of Elvenkind, a level of Druid to be able to use the Staff of the Woodlands. Let's assume you get a Manual of Quick Action, too.

That adds up to 12 (Prof with Expertise) + 6 (22 Dex) + 10(Pass Without Trace from Staff of the Woodlands) + 20(max attribute check roll, rolled at Advantage due to the Cloak/Boots of Elvenkind) = 48. Anyone attempting to view the hiding character would do so at Disadvantage (due to the Cloak/Boots of Elvenkind). Could go to 52 if cleric/druid cast Guidance on them (couldn't do it themselves because it's a Concentration spell, as is Pass Without Trace.

 

[CTurbo]

This is not so much a character that I plan to play. I'm just off today and it's storming outside so I was bored lol

I just like random discussion threads like these. It's fun to speculate.

I've never seen a 3+ class multiclass at any of my tables, and even then, I haven't seen very much multiclassing at all in actually game play.

 

[Pathkeeper24601]

For this I would go with a Gloom Ranger and Rogue or Bard. The second is a little hard on the stats, but invisibility to darkvision and expertise goes a long way to keeping you out of sight in the dark. Throw in a few illusion/support spells from the Bard and you have the ability to distract as well.

 

[mach1.9pants]

True can't argue that, but that's boring so how about NO Druids wildshaping into insects allowed lol

Spiders are arachnids /pedant