Starts out with Gloomstalker Ranger for 9 levels. This is a very strong subclass that needs little explanation.
Key pickups: Level 1: I went with Wood elf. It isn't necessary, but the extra movement works and you can pick up Elven Accuracy later. Level 2: Blindfighting and Fog Cloud at the same level. This is one of our first larks. Against any foe that lacks blindsight or tremor sense, you're always going to have advantage and they're always going to have disadvantage. You won't be concerned with opportunity attacks most of the time since unless they can see you'll just walk away. Using TCOE's optional class features, we're going with Deft Explorer. Level 3: Gloomstalker Level 4: Elven Accuracy (DEX). Not neecessary, but pairs well with our first malarkey. Level 5: You'll be getting Pass Without Trace for free later. If your party can live without it for at least 5 more levels, skip it here. Otherwise, it's an amazing spell and you should take it to apologize to them for using this build. Level 6: If you're using TCoE's optional class features, you just got another 5' of movement Level 7: Gloomstalker is going to give us Wisdom save proficiency. This is pretty important to late-game builds.
Level 9: Plant Growth - One of our mid-to-late game larks which can be used in conjunction with our first lark. In pretty much any natural terrain you'll be able to cast this spell. The duration of this spell is instantaneous meaning while the plants are affected by the spell in the way the spell says, they are not magical plants after it is cast. It can't be dispelled in the same way fireball can't be dispelled or for contrast in the way Transmute Rock can be dispelled. Furthermore, since they aren't magical plants but overgrown normal ones and you got Land's Stride at 8th level, they're not going to impede your movement. Everyone else is going to be having a bad time, spending 4' of movement to travel 1'. On a grid, moving one square within this effect costs 20' of movement and if you don't have enough movement to buy your way into the next square, you don't move. With a move of 30, a creature can go one grid square or two if they dash. As a wood elf with the TCoE Deft Explorer feature, you'll be moving 8 and comfortably outpacing anything that lacks a flight speed. In most circumstances, you should be able to dance circles around the enemy.
At this point, get a rule check. If your DM allows that overgrown plants can provide light obscurement, you'll want to take advantage of Wood Elf's Mask of the Wild with two levels of Rogue for Cunning Action.
If not, we're going right into Cleric.
Cleric 1: Trickery Domain. Don't worry, we don't care that it has a bad channeled divinity. Since Tasha's came out, we'll be using CDs to get spell slots back and we're more interested in the spells this subclass provides. Cleric 3: You just got Pass Without Trace and Mirror Image free. Our armor is not great, though you probably won't get attacked much and when you do you'll hopefully be countering it with Fog Cloud to impose disadvantage. Cleric 4: We're going to start pumping WIS. If you had an odd score, grab a half-feat. If you had an even score, go full ASI. Cleric 5: Probably not going to use Blink a lot, but it's free, as is Dispel Magic which you'll definitely find uses for. Cleric 6: 2nd Channeled Divinity... more spells. Cleric 7: You just got Polymorph and Dimension Door for free. These spells are larks unto themselves. Cleric 8: Final ASI for this build. Make sure your WIS or DEX are at max. I suggest WIS. Also, blessed strike for a paltry D8 bonus to damage, but whatever. Cleric 9: Only go past this point if you aren't taking 2 levels of rogue or if you like what you can upcast to 8th level more than you like cunning action.
As a multiclass caster, you will have 7th level spell slots (or 8th level if you bypass the 2 levels of rogue). There's not much to do with those slots except Upcast and the big candidates are going to be Spiritual Weapon at either 6th level or 8th level; Spirit Guardians, or Aid with the 7th level; and Bestow Curse with 5th level at which point it is non-concentration. Concentration should be used on Fog Cloud, Spirit Guardians, Summon Celestial, Conjure Animals, or Dominate Person.
A note on Spirit Guardians, when used in conjunction with Plant Growth, enemies with 30' of movement will have 15' of movement. Since 20' of movement will be needed to get to another square, they must take the dash action in order to move their new limit of one square (you'll still be moving 7 and possibly dashing as a rogue).
Notable Larks: You're a gloomstalker. Is it dark? You're invisible to anything relying on darkvision. Is it magically dark? You can see for 10' anyway. On the first round of combat, you get an extra attack which does an extra D8 of damage if it hits. Standard gloomstalker stuff.
As built our ending stealth is +16 with this character boosted to +26 with PWT. I went with Investigation for my Deft Explorer double-proficiency score anticipating that this character would do some scouting and trap detection. You could switch this around to something more suitable for your group.
I took Telekinetic for the ability to shove as a bonus action. This isn't necessary if you can disengage with your bonus action, but can be useful and opens up some options for layering spike growth on top of your plant growth.
The late-level cleric list kind of sucks while Ranger (as a half-caster) front-loads its spells from the perspective of a full caster. There's a lot of upcast room to compensate you for the lack of higher-level spells and multiple ways the build can screw with an encounter. Unfortunately, the build is a little self-centered in that regard, sacrificing allied plays or forcing them to work around you more than with you.
One thing to consider is that you can't swap your Ranger spells unless you take a Ranger level. So if you took Pass without Trace as a Ranger you now have redundancy unless you fix it by taking another Ranger level later or dropping it before going into Cleric.
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I'm trying my hand at doing a build. The damage is okay, but where it's really going to shine is messing with people.
https://www.dndbeyond.com/profile/FourShadows/characters/54486493
Starts out with Gloomstalker Ranger for 9 levels. This is a very strong subclass that needs little explanation.
Key pickups:
Level 1: I went with Wood elf. It isn't necessary, but the extra movement works and you can pick up Elven Accuracy later.
Level 2: Blindfighting and Fog Cloud at the same level. This is one of our first larks. Against any foe that lacks blindsight or tremor sense, you're always going to have advantage and they're always going to have disadvantage. You won't be concerned with opportunity attacks most of the time since unless they can see you'll just walk away. Using TCOE's optional class features, we're going with Deft Explorer.
Level 3: Gloomstalker
Level 4: Elven Accuracy (DEX). Not neecessary, but pairs well with our first malarkey.
Level 5: You'll be getting Pass Without Trace for free later. If your party can live without it for at least 5 more levels, skip it here. Otherwise, it's an amazing spell and you should take it to apologize to them for using this build.
Level 6: If you're using TCoE's optional class features, you just got another 5' of movement
Level 7: Gloomstalker is going to give us Wisdom save proficiency. This is pretty important to late-game builds.
Level 9: Plant Growth - One of our mid-to-late game larks which can be used in conjunction with our first lark. In pretty much any natural terrain you'll be able to cast this spell. The duration of this spell is instantaneous meaning while the plants are affected by the spell in the way the spell says, they are not magical plants after it is cast. It can't be dispelled in the same way fireball can't be dispelled or for contrast in the way Transmute Rock can be dispelled. Furthermore, since they aren't magical plants but overgrown normal ones and you got Land's Stride at 8th level, they're not going to impede your movement. Everyone else is going to be having a bad time, spending 4' of movement to travel 1'. On a grid, moving one square within this effect costs 20' of movement and if you don't have enough movement to buy your way into the next square, you don't move. With a move of 30, a creature can go one grid square or two if they dash. As a wood elf with the TCoE Deft Explorer feature, you'll be moving 8 and comfortably outpacing anything that lacks a flight speed. In most circumstances, you should be able to dance circles around the enemy.
At this point, get a rule check. If your DM allows that overgrown plants can provide light obscurement, you'll want to take advantage of Wood Elf's Mask of the Wild with two levels of Rogue for Cunning Action.
If not, we're going right into Cleric.
Cleric 1: Trickery Domain. Don't worry, we don't care that it has a bad channeled divinity. Since Tasha's came out, we'll be using CDs to get spell slots back and we're more interested in the spells this subclass provides.
Cleric 3: You just got Pass Without Trace and Mirror Image free. Our armor is not great, though you probably won't get attacked much and when you do you'll hopefully be countering it with Fog Cloud to impose disadvantage.
Cleric 4: We're going to start pumping WIS. If you had an odd score, grab a half-feat. If you had an even score, go full ASI.
Cleric 5: Probably not going to use Blink a lot, but it's free, as is Dispel Magic which you'll definitely find uses for.
Cleric 6: 2nd Channeled Divinity... more spells.
Cleric 7: You just got Polymorph and Dimension Door for free. These spells are larks unto themselves.
Cleric 8: Final ASI for this build. Make sure your WIS or DEX are at max. I suggest WIS. Also, blessed strike for a paltry D8 bonus to damage, but whatever.
Cleric 9: Only go past this point if you aren't taking 2 levels of rogue or if you like what you can upcast to 8th level more than you like cunning action.
As a multiclass caster, you will have 7th level spell slots (or 8th level if you bypass the 2 levels of rogue). There's not much to do with those slots except Upcast and the big candidates are going to be Spiritual Weapon at either 6th level or 8th level; Spirit Guardians, or Aid with the 7th level; and Bestow Curse with 5th level at which point it is non-concentration. Concentration should be used on Fog Cloud, Spirit Guardians, Summon Celestial, Conjure Animals, or Dominate Person.
A note on Spirit Guardians, when used in conjunction with Plant Growth, enemies with 30' of movement will have 15' of movement. Since 20' of movement will be needed to get to another square, they must take the dash action in order to move their new limit of one square (you'll still be moving 7 and possibly dashing as a rogue).
Notable Larks:
You're a gloomstalker. Is it dark? You're invisible to anything relying on darkvision. Is it magically dark? You can see for 10' anyway. On the first round of combat, you get an extra attack which does an extra D8 of damage if it hits. Standard gloomstalker stuff.
As built our ending stealth is +16 with this character boosted to +26 with PWT. I went with Investigation for my Deft Explorer double-proficiency score anticipating that this character would do some scouting and trap detection. You could switch this around to something more suitable for your group.
I took Telekinetic for the ability to shove as a bonus action. This isn't necessary if you can disengage with your bonus action, but can be useful and opens up some options for layering spike growth on top of your plant growth.
The late-level cleric list kind of sucks while Ranger (as a half-caster) front-loads its spells from the perspective of a full caster. There's a lot of upcast room to compensate you for the lack of higher-level spells and multiple ways the build can screw with an encounter. Unfortunately, the build is a little self-centered in that regard, sacrificing allied plays or forcing them to work around you more than with you.
One thing to consider is that you can't swap your Ranger spells unless you take a Ranger level. So if you took Pass without Trace as a Ranger you now have redundancy unless you fix it by taking another Ranger level later or dropping it before going into Cleric.