BDC is responsible for the Insanity that follows.
I have a limited in-game experience with monks. I’m not sure if any other DMs have hada few of their players go the monk route or if it’s just me. But the one example I had was a bad one. He was an optimizer, which, in and of itself, isn’t bad, but he was the type of guy who wanted to be superman. He wanted magic items; the type that break a game. He also wasn’t happy unless he was breaking the laws of physics or even the game itself. I don’t know how many times this careless DM had to end a session just to go study the rules to see where this was going wrong, only to realize that the monk’s player was simply fudging the rules and thought he was pulling one over on me. It usually involved a dragon or equivalent and it was a continuous test.
In the end, he multi-classed in Warlock (Obvious choice for quick easy power), was drawn in by a demonic power and became a herald for the end of times. And, much like the days of the old D20 Star Wars game, once he fell to the dark side, he lost control of the character. It was a joint decision and he was ready to move on anyway.
After all of that, the player is no longer with us (moved away) and the character is still under my power as a minion in the devices of a greater evil.
But, even after saying all of that, the worst part was his portrayal of a monk. It made me think heavily about what a monk actually is and isn’t. For him, a monk was a character who had taken a vow of poverty ending up many times naked in my game and begging for water from the tavern owner. This annoyed me greatly until I realized this stemmed from two things: The way he saw monks and his mischievous sense of humor.
What is a monk then? Well, like in all classes, it means many different things to many different people. It is, as it always is for roleplaying, in the hands of the player. The aforementioned player had a different idea about what a monk was. And, to a point, that is ok. But we, many times have a real narrow view of what a monk actually is.
Luckily, we have had a taste of good monk builds and development in the form of Beau from Critical Role. Sure, we have the expected martial arts, but we also see a rather intelligent, info broker who is as studied as she is talented with her fists. But there are a myriad of elements in the building of any character and, yes, even a monk, that can make your monk a dynamic and unique individual.
A Monk is more than Kung Fu
The first element I would like to look at is the varied fighting techniques available to us just from the world around us. Needless to say, one way you can differentiate your monk is by plugging in a particular fighting style. Now, I could spend articles writing about the varied styles of marital arts that are currently being practiced today. You can basically do the research on any number of them and make monk who is more defensive, uses mostly strikes or mostly kicks; the sky’s the limit.
BUT the monk is more than simply a martial artist!
The basis of the monk is unarmed combat. And, if making a Kung Fu master or a shaolin or ninja doesn’t appeal to you, there are many other disciplines out there to take cue from that bring with them a great deal of flavor.

CAPOEIRA or even the North African Dambe is a fighting style that is fueled by the rhythm and music of the culture. It is a mesmerizing movement that is poetry in motion. What’s more, you can team this monk up with a bard who can provide the beat in which inspires (Quite literally) them to beat their opponent. Lots of flavor here and you don’t have to make it an African motif as the music and fighting style can be molded to just about any culture.

SUMO may not be the first thing you think about when I say monk, but it is a discipline of which initiates cloister together in monastery like structures to learn the ways of sumo. This kind of monk would probably be stronger than most others since their focus is to over power their enemy, anchor themselves in place and knock you enemy prone or several feet away.

WRESTLING (or maybe pro wreslers) would be a good discipline for a monk that we do not usually think about, but it is unarmed and can, once again, benefit from a strength build. Possibly when homebrewing your way, you can accentuate the grapple and power moves. OR go a bit more MMA with a striker. A gladiator background with a bit of performance proficiency would help this build too.

YAGLI GURES (Turkish Oil Wrestling) as seen on the Van Damme movie THE QUEST and, more recently, in the Street Fighter character, Hakan, takes wrestling to a different level. Using the oil to make yourself difficult to grapple. It may be a bit one dimensional, but that’s in your hands to change things up.

SAVATE, MUAY THAI along with a myriad of other styles that center on the use of kicks either low or high and may or may not make use of chops and slaps. There are a myriad of variations to this theme or Kickboxing. Pick one or do a mix. Make your own style.
As said, you can plug in any fighting style here from SAMBO, SILAT, KRAV MAGA, Simoan LIMALAMA among a million of others. This can not only give a myriad of style, but allow anyone from any culture to bring their own monk from their own heritage.

Another way to outfit your monk in individuality is to take on the visual styles of animal inspired martial arts. They all have their own elegant and artistic way of approaching a strike. Predominant is the FIVE ANIMALS featuring the five forms of TIGER, CRANE, LEAPARD, SNAKE and DRAGON. Other styles are MONKEY, MANTIS, BEAR, etc. You name the animal, there seems to a style attributed to it.
Imagine a Kenku practicing CROW style or a Dragonborn fighting DRAGON style or a human exercising DUCK, CHICKEN or TURTLE style.
MAKE SURE YOUR MONK IS GOING THE RIGHT WAY
5E opened up with the WAY OF THE OPENED HAND, THE WAY OF THE FOUR ELEMENTS and THE WAY OF SHADOW in the PHB. From there we have gotten a few others, but it doesn’t seem that the monk gets as much as the other classes. Maybe it’s because this class is the hardest to dress up and accessorize. I don’t think so. But it seems Wotc feels that way.
The WAYS given are flavorful in their own right. SHADOW with its shadow, silence and pass without a trace. The FOUR ELEMENTS giving your awesome design with fire, wind, water and earth. I would think a Gensai would make a good adept at this Way. The OPEN HAND I believe is more toned for the vanilla monk, but still has its color.
Two that give some decent flavor are both found in Xanathar’s Guide to Everything.
The WAY OF THE KENSEI brings weapons into the fray. You get to pick a melee and a ranged weapon as your ‘Kensei Weapons’. These weapons are like an extension of your very body. You gain everything from pluses to AC, extra damage, artistic supply and rerolls. This gives you a samurai feel to your monk and keeps your options open to a myriad of weapons to choose from.
JACKIE CHAN IN LEGEND OF THE DRUNKEN MASTER KENSEI BY ALASSANDRO ROSSI
The WAY OF THE DRUNKEN MASTER is probably the most creative WAY Wotc has ventured into and they only went there because the fans wanted it. Movies like Jackie Chans THE LEGEND OF THE DRUNKEN MASTER popularized this brand of organized chaos. Truly coming across like a drunkard along with all the bucking and weaving and that ‘tipsy sway’; don’t be deceived. That last word is not a joke. Your character knows exactly what they’re doing whether or not your opponent believes this to be so. PIRATES OF THE CARRIBIAN’S Jack Sparrow comes to mind sans the sword.
WHEN ALL ELSE FAILS: HOMEBREW
Outside of homebrew, I’ve never seen a barroom brawler. In the long run, I will make one, because I can totally see a brawler type that loves nothing more than break into a barfight. Improvised weapons and so much more.
I also think we could take flavor ques from the movies to make quite unique monks. Although both are quite insane and slightly impractical, it would still make for a visual feast.
JOHN WICK (SUMMIT ENTERTAINMENT) EQUILIBRIUM (DIMENSION FILMS)
The most insane is GUNKATA or GUN FU. It is a martial art that is built around fire arms of all types. Now, you as a DM will have determine how far is too far (just mentioning this may be too far) but it is doable. GUN FU was showcased in my favorite Christian Bale movie (yeah, I said it!), EQUILIBRIUM and also John Wick. This type of Monk way would take fire arms from a ranged weapon to close combat. Now, you would have to make it comparable to their normal damage to be fair. But for the flavor and plain fun roleplaying, I think that it would be worth it.

Not as insane, but still a bit weird is the fictional martial arts from the movie REMO WILLIAMS. Based on the DESTROYER book series, written by Warren Murphy and Richard Sapir, SINANJU was touted as a Korean martial art. I never read the books, but I remember the movie and sensei who could dodge bullets, walk on water and immobilize opponents with simple strikes. I just think having a highly evasive monk who, if he gets a shot on you, has a chance to drop you would be worth looking into. I mean, One Punch Man as a D&D Monk sort of.
We will revisit this class and many others as I love to look into ways of adding flavor to your character build. As always, if you have any questions, suggestions or examples of the above drop them in the comments below or hit us up on Facebook, Twitter or Instagram! Let us know if there’s something specific you want us to talk about. And, as a parting challenge…. TABAXI MONK…that is all.