The most powerful rogue is the one you have the most fun playing.
There isn't going to be one answer that is the best; every archetype and race is good for different things. No one combination is going to be the best at everything.
Find a combo that fits a backstory that you enjoy, and go from there. Story driven RPG's, and story-driven characters, are without a doubt the best to play. The mechanics will be secondary.
Most OP to fun: Whatever you imagine and want to play. My personal recomendation.
Most OP Skill-Monkey: Half-elf Rogue(1)/Knowledge Cleric(1)/Lore Bard(4)/Ranger(1) with Skilled Feat (proficiency with all skills at lvl 7). But I'm sure this isn't funny for your group.
Most OP in Combat: I'm not sure, I'm not a MinMaxer but I think Assassin Rogue/Shadow Monk
Most OP to fun: Whatever you imagine and want to play. My personal recomendation.
Most OP Skill-Monkey: Half-elf Rogue(1)/Knowledge Cleric(1)/Lore Bard(4)/Ranger(1) with Skilled Feat (proficiency with all skills at lvl 7). But I'm sure this isn't funny for your group.
Most OP in Combat: I'm not sure, I'm not a MinMaxer but I think Assassin Rogue/Shadow Monk
With the build you posted, you get:
2 from Half-Elf
4 from Rogue(1)
2 from Cleric(1) Knowledge Domain
1 from Bard(1)
3 from Bard(3) Lore College
3 from Bard(4) Feat "Skilled"
1 from Ranger(1)
This gives you only 16 of the 18 skills and none of the 9 tools such as a Disguise Kit or Thieve's Tools. To get the other two skills you would need to use your background skills in something like Urban Bounty Hunter, choosing ones that do not overlap with limited skill sets like the rogue's and ranger's. You would not get all the kits until you got 3 more Ability Score Increases to dump into Skilled feats. Also, all of this multiclassing would require a 13 or higher in Dex, Wisdom, and Cha, making you weak in terms of fighting with low stats going to con and str, and weak at spellcasting, since Rogue and Ranger gave you no spell slots, putting you a whole spell level down in progression. So yeah, you could sneak into a place, see everything, know all about the people and things in there, perform acts of strength balance, and entertainment, and convince them not to outright murder you, but you would not actually do anything constructive.
You also wasted a bunch of ASIs on feats, so your stats would never go up, making all of the skill proficiencies relatively weak without the stats to back them up.
You'd also be better taking Warlock(2) over Ranger(1) since you get spell slots from each warlock level (unlike Ranger) and at Lvl2 you get the Eldritch Invocation, Beguiling Influence which gives you two skills, and Devil's Sight which gives you darkvision to 120' instead of 60, allowing you to make perception checks at greater distance, and it allows you to see in magical darkness.
Of course I counted with the Background skills (you can choose any background which gives you two skills which you choose already from the rogue list so you actually have 2 free pick, or made your own Background with the custom background rules). And I have proficiency with Thieve's Tool 'cause start as Rogue, and can have Disguise and Poisoner Kit if after done with multiclassing I go for Assassin archetype. No more tools are really so needed (maybe Navigator's if you are in a Pirate/Sea Campaign which I could pick from the custom background).
So only one ASI burn to feat, and this build is for a skillmonkey, not for a Toolmonkey, not for a Skillmonkey/GoodFighter/GoodSpellcaster all 3 in 1. Anyways you start with a nice DEX (16, with the standard array) to do "constructive" things (And constructive here means kill mobs). But the build is focus to do things (almost everything) outside combat, and it is useful and do a lot of constructive things.
Warlock is a good option also and everyone wants Devil's Sight, but requires 2 levels. Ranger 1 gives more damage to one type of creatures (Humanoids is my choice) and a lot of advantages. So maybe both classes are an option and the choice is about if you want to be more spellcaster or fighter.
I was actually working on something like this for one of my games I am in. Currently we are 4th level and I am Rogue 2, Cleric (knowledge) 1, Mystic (Nomad) 1. The nomad mystic means you are proficient in whatever you want to be proficient in with Nomadic Mind and you have two more free slots that you can change out each day. Also, Nomadic Arrow helps you with your combat skill, and you can be focused on ranged attacks. As for spellcasting, the character really isn't designed for that, the cleric spells he chooses are simply buff spells.
I plan to take rogue to level 11 for the reliable talent feature so he'll feel like a real skill monkey. I'm leaning towards Mastermind Rogue and using him as much for support in combat as anything. But, the UA Scout rogue would add some extra proficiencies that he lacks as well. The character has a 16 Dex as well as 14 in each of Int, Wis & Chr. And also worth noting that the Cleric spell Guidance is fantastic for this character.
DM in the kobold fight club "Yes i know this is insane, but my usual players are murderhobos." Birdman in adventures in faerun "Flapping wings" (telepathy) "The enemies are overwhelming us, i'll go break their minds." Irthos Bladesinger in trouble in timberbottom (DED) (All PbP)
Swashbucklers and Arcane Tricksters are considered top tier sub classes, a fighter dip gets you action surge and two weapon fighting style which is great to help make sure you get sneak attack and increase your DPR (and some extra HP, offers you a shield and dueling if you don't want to dual wield for whatever reason).
If you want to crit fish you could take it far enough to pick up the champion fighter 19-20 benefit (would actually combo pretty well with halfling, which is a good race for you, as a result of lucky) but i'm not sure that warrants the drop in sneak attack damage overall.
Speaking of races Forest Gnomes, Halflings (Lightfoot for Swashbuckler, Stout more generally), and Elves (High Elf for AT, Drow for Swashbuckler, Wood Elf for others), Half Elves all make pretty solid rogues. Out of the player's handbook, variant 'feral' tieflings make wonderful arcane tricksters, tabaxi make excellent swashbucklers, Kenku are fine general rogues as well. Basically anything with a dex bonus is in the running here, the secondary stat they have can usually contribute to a subclass, or will determine how you formulate your skills.
Addendum: I would postulate a very optimized rogue build, as being a Lightfoot Halfling Swashbuckler who keeps Charisma and Dexterity co-primary, takes 3 levels in fighter (for the champion level 3 benefit, the fighting style for dual wielding.) Maybe take Dual Wielder once they have Dexterity and Charisma maxed out to dual wield rapiers for the extra 2 damage an action that would qualify you for, and further capitalize on critfishing.
Recently saw a build that was 5-6 levels of the UA Ranger to go into Deepstalker conclave and then going into the Assassin Rogue. Starting the combats with 4 attacks with advantage (5 if you dual-wield) and an add in of Hunter's Mark and Favored Enemy to really bring in a bit of hurt.
As far as damage goes i think an archer assassin is the best advantage from stealth X4 damage because assassin and a +10 for shits from sharpshooter. Dunno just my guess
I built a multi class skill monkey rogue out of Half Elf, rogue/bard and instead of a two level dip into cleric of knowledge (which would have gotten 2 additional skills) decided on a 2 level dip into Druid, circle of the moon. Any time you can use it to literally turn yourself into a newt, and quote Monty Python in game, will always be a win. Especially when trying to con shop keepers out of their goods with good deception and slight of hand rolls, by convincing onlookers the shopkeeper is selling ‘cursed’ items, but that you did “get better”.
Rogue (assassin) 17/paladin (oathbreaker) 3. Assassin subclass let you double the damage dealt against surprised targets, at lvl 17 you may also double the damage again; oathbreaker's channel divinity gives you advantage for 1 min; sentinel (more opportunity attacks), lucky and dual wielder feats; and divine smite.
what would be the most powerful rogue?
Level 20.
:D
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I mean what sub class with what race and what feats, what multiclass, those kinda of things
The most powerful rogue is the one you have the most fun playing.
There isn't going to be one answer that is the best; every archetype and race is good for different things. No one combination is going to be the best at everything.
Find a combo that fits a backstory that you enjoy, and go from there. Story driven RPG's, and story-driven characters, are without a doubt the best to play. The mechanics will be secondary.
PBP: DM of Titans of Tomorrow
PBP: Lera Zahuv in Whispers of Dissent
PBP: Evaine Brae in Innistrad: Dark Ascension
PBP: Cor'avin in Tomb of Annihilation
Most OP to fun: Whatever you imagine and want to play. My personal recomendation.
Most OP Skill-Monkey: Half-elf Rogue(1)/Knowledge Cleric(1)/Lore Bard(4)/Ranger(1) with Skilled Feat (proficiency with all skills at lvl 7). But I'm sure this isn't funny for your group.
Most OP in Combat: I'm not sure, I'm not a MinMaxer but I think Assassin Rogue/Shadow Monk
D&D Beyond Mobile Alpha Tester
You'd also be better taking Warlock(2) over Ranger(1) since you get spell slots from each warlock level (unlike Ranger) and at Lvl2 you get the Eldritch Invocation, Beguiling Influence which gives you two skills, and Devil's Sight which gives you darkvision to 120' instead of 60, allowing you to make perception checks at greater distance, and it allows you to see in magical darkness.
Of course I counted with the Background skills (you can choose any background which gives you two skills which you choose already from the rogue list so you actually have 2 free pick, or made your own Background with the custom background rules). And I have proficiency with Thieve's Tool 'cause start as Rogue, and can have Disguise and Poisoner Kit if after done with multiclassing I go for Assassin archetype. No more tools are really so needed (maybe Navigator's if you are in a Pirate/Sea Campaign which I could pick from the custom background).
So only one ASI burn to feat, and this build is for a skillmonkey, not for a Toolmonkey, not for a Skillmonkey/GoodFighter/GoodSpellcaster all 3 in 1. Anyways you start with a nice DEX (16, with the standard array) to do "constructive" things (And constructive here means kill mobs). But the build is focus to do things (almost everything) outside combat, and it is useful and do a lot of constructive things.
Warlock is a good option also and everyone wants Devil's Sight, but requires 2 levels. Ranger 1 gives more damage to one type of creatures (Humanoids is my choice) and a lot of advantages. So maybe both classes are an option and the choice is about if you want to be more spellcaster or fighter.
D&D Beyond Mobile Alpha Tester
I was actually working on something like this for one of my games I am in. Currently we are 4th level and I am Rogue 2, Cleric (knowledge) 1, Mystic (Nomad) 1. The nomad mystic means you are proficient in whatever you want to be proficient in with Nomadic Mind and you have two more free slots that you can change out each day. Also, Nomadic Arrow helps you with your combat skill, and you can be focused on ranged attacks. As for spellcasting, the character really isn't designed for that, the cleric spells he chooses are simply buff spells.
I plan to take rogue to level 11 for the reliable talent feature so he'll feel like a real skill monkey. I'm leaning towards Mastermind Rogue and using him as much for support in combat as anything. But, the UA Scout rogue would add some extra proficiencies that he lacks as well. The character has a 16 Dex as well as 14 in each of Int, Wis & Chr. And also worth noting that the Cleric spell Guidance is fantastic for this character.
Level 20 Half-orc rogue, Assassin.
With the storm giant belt of strength, you can deal about 270 damage in your first attack. And uh.... LOOK AT THAT DAMAGE.
I'm that cat guy, and i do stuff. Youtube account: https://www.youtube.com/channel/UCGyrtkNMBOOCxyH4Eueno3w
Tabaxi Bard Level 15
DM in the kobold fight club "Yes i know this is insane, but my usual players are murderhobos."
Birdman in adventures in faerun "Flapping wings" (telepathy) "The enemies are overwhelming us, i'll go break their minds."
Irthos Bladesinger in trouble in timberbottom (DED)
(All PbP)
Swashbucklers and Arcane Tricksters are considered top tier sub classes, a fighter dip gets you action surge and two weapon fighting style which is great to help make sure you get sneak attack and increase your DPR (and some extra HP, offers you a shield and dueling if you don't want to dual wield for whatever reason).
If you want to crit fish you could take it far enough to pick up the champion fighter 19-20 benefit (would actually combo pretty well with halfling, which is a good race for you, as a result of lucky) but i'm not sure that warrants the drop in sneak attack damage overall.
Speaking of races Forest Gnomes, Halflings (Lightfoot for Swashbuckler, Stout more generally), and Elves (High Elf for AT, Drow for Swashbuckler, Wood Elf for others), Half Elves all make pretty solid rogues. Out of the player's handbook, variant 'feral' tieflings make wonderful arcane tricksters, tabaxi make excellent swashbucklers, Kenku are fine general rogues as well. Basically anything with a dex bonus is in the running here, the secondary stat they have can usually contribute to a subclass, or will determine how you formulate your skills.
Addendum: I would postulate a very optimized rogue build, as being a Lightfoot Halfling Swashbuckler who keeps Charisma and Dexterity co-primary, takes 3 levels in fighter (for the champion level 3 benefit, the fighting style for dual wielding.) Maybe take Dual Wielder once they have Dexterity and Charisma maxed out to dual wield rapiers for the extra 2 damage an action that would qualify you for, and further capitalize on critfishing.
Recently saw a build that was 5-6 levels of the UA Ranger to go into Deepstalker conclave and then going into the Assassin Rogue. Starting the combats with 4 attacks with advantage (5 if you dual-wield) and an add in of Hunter's Mark and Favored Enemy to really bring in a bit of hurt.
As far as damage goes i think an archer assassin is the best advantage from stealth X4 damage because assassin and a +10 for shits from sharpshooter. Dunno just my guess
I like a Kobold Arcane Tricksters with find familiar for pack tactics, with the feats crossbow expert and sharpshooter
I built a multi class skill monkey rogue out of Half Elf, rogue/bard and instead of a two level dip into cleric of knowledge (which would have gotten 2 additional skills) decided on a 2 level dip into Druid, circle of the moon. Any time you can use it to literally turn yourself into a newt, and quote Monty Python in game, will always be a win. Especially when trying to con shop keepers out of their goods with good deception and slight of hand rolls, by convincing onlookers the shopkeeper is selling ‘cursed’ items, but that you did “get better”.
Rogue (assassin) 17/paladin (oathbreaker) 3. Assassin subclass let you double the damage dealt against surprised targets, at lvl 17 you may also double the damage again; oathbreaker's channel divinity gives you advantage for 1 min; sentinel (more opportunity attacks), lucky and dual wielder feats; and divine smite.
Locking due to necromancy; Please start a new thread with current & active individuals, if needed.
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Send me a message with any questions or concerns