Whether this thing qualifies as a 'monster' is probably up for debate - it is certainly monstrous but I doubt any DM is cruel enough to chuck this maniacal mandrill on their random encounter table. This beastie was actually statted up in 1e (Or OGD&D as I like to call it.) In the golden age of 1d4 hit points some people were apparently crazy enough to go toe-to-tentacle with the Prince of Demons himself.
This is it - the final boss, the biggest of cheeses. In the final battle of your campaign your near-godlike PCs are going to scrap with Demogorgon.
Art
We essentially have two pieces here, as Demogorgon is the cover model for Out of the Abyss and merits a two-page spread inside.
The cover shoot gives a great sense of scale, in a way only a full A4 piece of art really can ( a full-size spread can be found here). I love his thrashing tentacles, his bestial roar - the fact that whole buildings are plummeting into the Underdark as he rampages. I particularaly like the sense that you are underfoot in this image - before Demogorgon your sparkly PC Paladin is little more than a self-righteous beetle with delusions of grandeur. Somehow the goofiness of the Demogorgon design ("it's a big monkey with tentacles") is eclipsed by the energy of this depiction. Not bad at all.
Within is a more personalised image of Big D which I like less. They've add uniformity to his form in contrast to his earlier depictions to try and give some cohesion to Demogorgon. Normally this would make me appreciate a piece more and it would seem less gonzo and silly....but this is Demogorgon! Shouldn't he be jarring and messed up and crazy and silly? Shouldn't he carry on being a giant grumpy squidaboon with the sheer panache and gravitas that comes from being an OG Demon Lord?
Purpose and TacticsWe are going to assume three things here.
1) You're fighting Demogorgon in his 'lair' - the depths of the Gaping Maw - in order to kill him for good. The kid gloves are off, Demogorgon.
2) You're throwing the CR calculation guidelines away for this one.
3) You didn't go for a deus ex machina maguffin or decide your players kill Demogorgon with the power of love or something.
Obviously Demogorgon needs minions - he's the Prince of Demons. I'd err on the side of things with less fiddly effects to track and deal with, so more Mariliths and Hezrou than Nalfeshnee or Glabrezu.
Your party are never going to disable Demogorgon with save versus effects - he has Magical Resistance and very, very high saves, and legendary resistance if they manage all of that, so it may be a case of disabling the minions and focusing fire on Demogorgon. He even has a special ability 'Two Heads' which nixes a number of disabling effects. He also needs an insane arena with which to battle the PCs - some kaleidoscopic panopticon in the depths of the Abyss with a host of environmental effects. A building where gravity changes every round and every reflective surface summons a hostile but illusory Mirror Image would add to the general chaos. There's also call for aquatic elements - a flooding room or underwater aspect to the arena would also complicate the fight significantly, and open the door to some aquatic lackeys of Demogoron like Aboleths or Sauhaugin or Chuul.
This is essentially a DPS race: the players need to get in and nova hard enough on Demogorgon to cut through almost 500 hit points whilst he disrupts them from doing that long enough to finish them off with his (and his minions) attacks.This encounter should take a session, minimum.
Demogorgon has an insane number of disabling effects to disrupt and confuse your party: he can drop numerous Gaze effects which afflict players with damaging effects, often ones with no save and requiring no concentration. I'd read carefully how these abilities interact (You can't use Hypnotic Gaze and then Maddening Gaze as your legendary action) and a number of them are for a single turn. Unless Demogorgon is supporting some minions his action economy is going to be torn between disrupting the PCs and actually taking the time to smack them about with his tentacles. Causing a player to potentially lose their turn for one turn is never worth Demogorgon's actual action because every other character will still be working against him. I'd ensure you use either the Tail or Tentacle attacks pretty much every round to keep the damage out-put constant. The Tail does significantly more damage but if your high-level party hasn't realised how incredibly inefficient in-combat healing is mashing them with the Tentacle can teach them the error of their ways by reducing the hit point maximum.
Both attacks also have decent Reach, meaning Demogorgon should be focussing fire and hammering weakened or squishy player-characters. You are playing for keeps with Demogorgon to try and ensure you finish off weakened players rather than spreading the damage around. With his action economy, you will find yourself struggling with which of the vast number of potential actions you should actually do. The Lair Actions are nicely disruptive - one is a version of Mirror Image, and the other lets you plant Darkness around the arena, and help ensure he is disrupting whilst still maintaining damage output with his tentacles and tail.
Demogorgon has some nasty tricks buried in his spell-casting. Most of this is pretty unhelpful in combat (Illusions, for example). One brutal example is that he has Feeblemind, which can essentially take a caster out of the fight. Aside from Wizards, very few characters will have decent Intelligence, so if you're targeting a Bard, Warlock or Sorcerer you can reduce them to using whatever abilities fit the loopholes of Feeblemind or stabbing Demogorgon for 1d6 +trash damage. Adding insult to injury, this player-character will be a drooling moron for at least a month and will probably fail every other save against Demogorgon's disruptive effects too. Fear deserves a mention as it is not single-target like many of Demogorgon's gaze attacks, I personally think Fear is even better when it doesn't affect the entire party, as some characters uselessly flee and others are left at Demogorgon's mercy. Telekinesis would be a waste of Demogorgon's action unless you have environmental effects that can cause some severe damage.
The biggest downside of this fight is your players are going to spend a fair amount of it disabled, confused or charmed. If your players find this frustrating (as many do) you might prefer to make your Big Bad Orcus or someone more straightfowardly damaging.
Built into his stat-block are variant rules that require you to use some form of sanity mechanic - I personally like this touch but it seems a bit pointless - if you're using a sanity mechanic you probably already have mechanics for everything here described. If you do utilise this, it could make the fight significantly more difficult as it essentially gives the players less ability to move.
Fluff
Much ink has been spilled on Demogorgon over the years and only his general conceptual wackiness keeps him on the rung below Orcus for most recognisable Demon. The tones of hyperbole on Demogorgon are, for once in WOTC's writing career, completely merited - this is the biggest bad of all the bads who wants to bring the bad to every corner of the cosmology. I love that the fluff opens with Demogorgon's nutty titles and end-goal.
Verdict: If you think your gods and demons lords should roll initiative and rumble with the rest of them, this write-up gives you a great starting point for a ruckus.
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