I’d look into going 3 assassin rogue so your initial barrage of attacks can all crit if the target is surprised, which they should be given this build. That also doubles the 2d6 bonus from bugbear’s Surprise Attack to 4d6.

I played in a group that had no rogue or front line fighters, so I decided to rock up with a bugbear barbarian with the skill expert feat and criminal background for thieves tools. Now I was open locked chests and doors, sneaking around completely undetected, and hitting harder that a rogue twice my level.

Another great one! I played this in Curse of Strahd as a Dhampir and it wrecked! Another combo to consider is Astral Self/Feywanderer. You can focus on WIS because all your attacks, STR checks and saves, and CHA checks get to use or add WIS to them.

I love this video because I played a Panther Tabaxi Way of the Shadow Monk and my character died twice before I could go into ranger. He was level 4 😅 and he died but got resurrected by a enemy then I was able to play him again. Second time I died to a poison spell then failed 3 death saves, rest in Peace Silent Shadow of Distant Rain. ❤

In my opinion, the best fighting style in this build is Blind Fighting, because you can capitalize on "Darkness" too if the fight needs it.

A thought on asking the DM where shadows are all the time, you could make that more proactive and either make shadows or take advantage of knowing where they will be. For example cantrips and common spells that emit light like Firebolt and Green Flame Blade will force shadows and you can ready a reaction to shadow step when the light casts the shadow. Alternatively you can do a little engineering and have party members attach a physical, or cast a magical, light source on their person. A hooded lantern on a belt, light cast on a tongue piercing or inside of a scroll case. With a little ingenuity your party would be able to enable your shadow step so that you could appear behind their opponent. Even if the party don't go for it, you can easily and cheaply prepare small flash bombs by wrapping a cup of bread flour in a bit of burlap with a wick so that when thrown the cloud of flour ignites, added bonus is that if your DM doesn't hate physics you might even disorient or stun the target as you teleport behind them. And my last thought is pay a blacksmith to make a special lantern with thin vertical slits, attach said lantern to an immovable rod, activate the rod in the middle of the room and throw shadows 360 degrees.

You could also use Shdar-ki to have teleports right of the bat, and extra teleports when shadows aren't available.

was just looking for a bugbear monk, perfect timing

Nice build. For a similar end result, via a somewhat different path... Mark of Finding, human or h.orc, from the Eberron setting. Among other things, you get a free use of Hunter's Mark. Now, instead of 3 levels of Ranger you can do 3 levels in Rogue (most choose Assassin, I'd go Arcane Trickster). Definitely still go into Fighter first for Action Surge though.

Cool build

For a bugbear monk/ ranger build I'm going with probably the funniest combination sunsoul / gloom stalker , i know it wastes the bugbear long reach in most cases but the 30 foot range means that you can take advantage of going first even if you can't get to close the distance for melee, and while its genuinely a very weak subclass the bugbear extra damage could make up for it , and yes you're probably going to have to sac an asi for the alert feat . I think it will make for an interesting build, not sure when for multi classing and what level split yet. I find the image of the character slipping through the ahadows unseen than bam a bolt of light comes from nowhere and the enemy seeing just a glimpse of the person who shoot the bolt before the darkness swallows them up again and disappear just as fast to be hilarious

You could try starting out fighter to get the unarmed fighting style so you can hit with a d8 from the beginning instead of a d4. Then do the regular progression as in the video. You would also get proficiency with martial weapons which means you can use a long sword with the monk’s dedicated weapon feature. Little bit of a power bump

I feel like monk is sort of having the mini resurgence ranger got after Tasha's now that we have more options for it. It sucks that it has a lot of features competing for its bonus action and you basically have to squeeze monk for all it's worth to get it to keep up with other classes, but it's still an enjoyable class. I have seen more than one monk player that felt a bit impotent because they didn't optimise their build. It has a lot of "noob trap" mechanics, like baiting players into putting too many points into Wisdom and then their Con sucks so they go down and can't hit anything, or they can't hit anything at later levels because their Dex can't compete with the rising AC of enemies. It feels a bit awkward to tell a new player that their class's most iconic feature depends on an ability score they shouldn't focus on... Your Dex also determines how successful your Stunning Strikes are.

Why not pick Blindfighting as a fighting style? - Would be great for darkness shadow monk.

Had an idea for a firbolg taking the fey lost background, take 3 in fey wanderer ranger, and take levels in knowledge cleric, prioritize wisdom and then intelligence, at one point it could have a +5 at least to all mental abilities if we focus on half feats such as skill expert. Image, a bovine firbolg with flowers growing from their hair, flowers around them bloom when in the presence of them, in combat you have that suggestion ability as well as shileghlegh, spirit guardians, spriitual weapon, all the cleric goodies and a skill monkey especially in all mentals

Kensei Monk/Ranger works well, try Kensei X/Swarm Keeper 3-5 with a longbow.

Either Shadar-Kai or Eldarin to enhance teleport abilities, i'd pick the dedicated weapon optional feature with monk and dip 3 lvls of Assassin rogue with the alert feat (+WIS cuz Gloomstalker) just to enhance damage with Sneak Attack on first round of combat... and 3 lvls in Champion Fighter to have Improved Critical and make it a damage dealing monster

So does surprise attack stack? Can it be used on one enemy, and then another through flurry of blows (or extra attack)? Keeping to the conditions of ability and bith enemies are in range?

For a fighting style how about Blind Fighting? Given you can make Darkness.

For me the Fighting Style that absolutely stands out to me is _Blind Fighting._ You can't look through the _Darkness_ spell using your darkvison... but you _can_ use Blindsight. And you can cast the _Darkness_ spell to give yourself a place to teleport to using _Shadow Step._ Unfortunately, you can't cast _Darkness,_ then teleport over there, then attack, since casting takes your action and teleporting your bonus action... unless you have, say, _Action Surge._ So take two levels in Fighter and also take the _Unarmed Fighting_ fighting style. That also lets you pick up a better _Dedicated Weapon_ for monk. So if your attack them while in Darkness and they can't see you, you get advantage on all you attacks and they get disadvantage on theirs.

Dang! Under dark killer!

Consider taking the Feat: Eldritch Adept "One with Shadows" (if your DM will allow it without being 5 levels of warlock) if you want to be an "ambusher"; just waiting on your target to come close and striking from invisibility. I'd also try to mix in the classic Assassin rogue for that Assassinate ability so that all of many hits we're doing are crits during the surprise round. For roleplay/non "combat", this would be an excellent literal assassin type character; sneaking into a target's bedroom/watercloset/someplace their guard is down, waiting for them in the shadows and guaranteeing a surprise

Bro, do you have a website or Discord, where do you leave this build with more details?

What's the connection between suprise round and advantage on our attacks? We are not assassin rogue.

Yes, I'm NOT going bugbear and not going Gloomstalker. I'm going wood elf and Hunter. I want to teleport into the center of a group of bad guys and whirlwind attack them all with double advantage! Maybe action surge again for another one. I don't like monster races. Drizzt was supposed to be unique. But because they loaded up monster races with cool abilities, players will choose the monsters and play them like halflings or half-orcs. With everything hunter rangers get to stack onto their damage, with the high chance of critting, you won't miss the gloom or the skulking.

Remember that hunters mark requires a weapon attack, so a monks FoB won’t trigger the extra damage. Hex would though Edit: this incorrect, per a Crawford ruling. Seems sus but ok.

This but a gunk

Fighter is interesting but the problem is the amount of bonus actions you're taking.. go rogue assassin 5lvs for 3d6 extra sneak and assassinate to get that crit and uncanny dodge to play it safe, 5lvs ranger gloomstalker for obvious reasons and 6lvs monk for obvious reasons.. shadar Kai make for better shock value when you teleport into a circle of foes and mame one only to have their counter attacks pass through you and potentially hit each other at 3rd lv.. the last 4 levels.. I've considered fighter but I draw a blank because taking 4 classes just to build this feels absurd. I feel like the gloomstalker and assassin were initially one class but they split it because of rogue sneak attack stigma.. kinda like why the shadow dancer is now a monk instead of decidedly rogue, sneak attack combined with low risk teleportation eliminates the use of other classes.. it's not ninjas and dragons ... Or is it!

I think there is no point to go shadow monk with this build. The action economy is not optimized. The whole point is to pop out of the shadows and Crack someone like you say BUT to shadow jump you use your bonus action therfore no flurry of blows. To follow his combat guide you would just sneak up like any other rogue so whats the point of going shadow monk? Truth us shadow monk is cool but you are going to be tickling people if you actually shadow jump. I suggest going defense with shadow monk. Don't bonus action up to an enemy, jump after you punch them 60 ft away then you can use your speed to move away another 60 ft and if you're tabaxi yeah you're gone! Then you sneak up and shadow jump away

Gloomstalker fighter with optionalnassassin stills sounds a little stronger. Echo knight if you enjoy poorly designed and completely broken homebrews. Preferably fighter 10+++ not that your campaign will get there but... A for effort. This can ofcourse be done with a big 2h or like a flametongue if you get it. People can ofcourse use elven accuracy or darkness but i dont enjoy abusing your party. Pass without trace from gloomstalker 5 is possible too. I have a gs5/fighter 3 and it is extremely solid. If near lvl 15 it would have been better to be an echo knight 11+ ofc but cba with the frowns aorund table when presenting the character and actually deserving it.

neat concept but its a meh for me, pass without trace easily ruins story arcs, i tend to stay away from its use, same with fly imo both break games the most. a few others do too.