Best Rogue for BearBarb5/Rogue15

[Snowbluff]

Thread title. Sword and Board barb with some extra tankiness and damage.
Bear bard for Resist all, Extra attack.
Rogue gives more skills, Uncanny Dodge, Evasion, more damage, etc.
Using Finesse weapons with Str.

[ciarannihill]

I personally like to do Assassin Rogue with Bugbear as the race for this style build. Gives an extra 2d6 when attacking from stealth, and if you have a surprise round you auto-crit on your attack. Also Bugbears get extra reach on melee weapons, and have Stealth Proficiency by default, meaning you can invest in other skills without worry.

There are plenty of other ways to go about it, though.

[rbstr]

Going the other way, which ones might not be too useful?
Arcane Trickster isn't going to work very well with rages.
Swashbuckler's free sneak attack and disengage aren't so important since you've got front-line staying power and easy advantage from reckless attack.
Inquisitive's easy insightful sneak attack feature is also not so important because of Reckless.

So for the archetypes that give you something:
Thief has the bonus action object use, climbing stuff, and stealth bonuses.
Assassin works pretty well with extra attack if you can surprise enemies and gives you good disguises.
Scout has some extra skills, extra movement, and a fun 1st-round party buff.
Mastermind's got some neat RP stuff, a cool party-buffing bonus action.

IMO I think I'd go Scout?

[GlenSmash!]

I'd go with Scout I'm a sucker for more movement and more Wilderness skill expertises.

[CTurbo]

Swashbuckler sounds the best, but makes you a bit more MAD since you want at least a little Charisma. I suppose you could stick a 12 there and be done. You could basically get sneak attack damage every single round.

Scout is ok, but you don't really want to run away from your enemies. In fact, I think Sentinel should be mandatory for this build so you can use sneak attack on your reaction each round too.

[JellyPooga]

Thief.

Using Fast Hands for terrain manipulation is all sorts of fun and gives you a resourceless battlefield control ability (assuming there's furniture knocking around). Very handy combined with the Bugbears extra reach.

I would also recommend not going Bear Totem; between regular Rage resistances, Uncanny Dodge and Evasion, you're already extremely tolerant towards incoming damage; often immune against many instances of non-B/P/S when it's AoE. In the mid-tier game, you may find yourself wishing you'd gone for Wolf or Elk Totem instead.