Technically, the first monsters that I ever had two players see were an Azer and an Efreeti, though neither was remotely hostile to the party. The big set-piece that I ran was one in which the campaign's big bad, a cult's prophet who had taken part in the conspiracy that destroyed the long-lost civilization that once spanned the world, used his eldritch powers to call upon the Tarrasque (thinking back, I think primarily by going "here I am, that aberration of all natural law that you exist to destroy,") which then went on to destroy most of the city that the party was in.
Of my three players, the one familiar with D&D, said "well, we're not ready to fight that," and I, brand-new novice DM that I was, thought "well, obviously I'm not expecting you to fight it. This is just a set-piece and a background event while your first fight is actually two kobolds and an octopus."
That encounter was actually balanced according to the 2014 DMG, but obviously, as anyone who has actually run this game would know, was far too easy - in fact, neither kobold even got a turn, falling before the Paladin and Fighter, and the octopus retreated into a jar only to be adopted (as I suspected it would) by the party.
In my early days DMing, I was excited to use every creature in the Monster Manual, and as such, I often pushed to try to use just one big monster in my fights. I'm actually not sure that this is always a losing strategy, but I struggled to challenge my players, such as when the Spectator boss of my first true dungeon was taken out in a single critical hit by the paladin (again, before it could get a turn in combat).
Only rarely do I actually run a combat with just a single monster, and if I do, it basically has to be a legendary monster to make up for the deficit in its action economy.
But we've seen a real re-balancing. The new Monster Manual has beefed up a lot of monsters, and while this is mostly true in the higher CR range, it's also true at lower levels. I'd also advise new DMs as well to remember that, as cool as a new, tougher monster is, even simpler, low-CR monsters can make for interesting fights if you have cool tactical opportunities. Ledges, destructible platforms, cover, and obstacles can make for more dynamic fights.
The encounter-building guidance in the new DMG is significantly more generous to a DM. (Also, building encounters for a three-player party is pretty limiting). This means that a fight is liable to be tougher.
Another word of warning to greenhorn DMs is that, the lower level your players are, the less wiggle-room you have to course-correct. Generally speaking, you want to present a challenge to your players but not to "beat" them. But at low levels, even if you're doing little more than just attacking with low-CR monsters like Kobolds or Goblins, a few unlucky rolls can kill a new character. As PC HP goes up, and as healing capabilities become available to the party, this gets less tenuous.
This post is primarily just going to be a list of CRs and their corresponding XP value. The way I'm evaluating this is whether a single creature of the given CR can be presented to a group of players at a given level and for its XP value to be equal to or less than the total budget for a High-difficulty encounter. Again, my sense (and this requires more playing with this system to know for certain) is that the new DMG's High-difficulty budget is genuinely, like, really quite difficult - a deadly threat in the way that the 2014 rules could only hint at.
Now, there is another question to ask: how many players are we talking?
In my experience, most D&D groups are 4-6 players. If we want to look at the earliest we can employ a creature of a given CR, naturally we could use a 6-player party to maximize our XP budget. But I think it might be wiser to look at the average here, sticking with 5 as a typical example (naturally, your table might differ).
CR 0, CR 1/8, CR 1/4, CR 1/2, and CR 1:
These challenge ratings represent creatures that are fairly weak and easy to take down. Even for level 1, none of these has enough XP to expend a full high-difficulty budget. But even if you're going for a Low-difficulty encounter (which you probably should when the party's just starting out in most cases) a single CR 1 monster is worth 200 xp, which would just fit for a 4-player party, and if we're at 5 players, you're actually below Low difficulty if that creature doesn't have any help.
CR 2, 450 xp: Level 1
If you have 5 or 6 player characters, each contributes 100 to the budget of a high-difficulty encounter, meaning a budget of 500 or 600. Thus, in theory, a party of five or six could take on a CR 2 monster like an Ankheg, though it would be a hard fight. Note, though, that an Ankheg's Bite attack deals an average of 13 damage to a target, meaning that it's unlikely anyone other than a Barbarian is going to remain standing after a single successful hit. It's highly unlikely that no one in the party will go down if the Ankheg gets a turn.
CR 3, 700 xp: Level 2
5 2nd level players have a high-difficulty budget of 200 apiece, meaning a total budget of 1000. This could thus allow you to send a Mummy against them along with 300 xp-worth of creatures to aid them (perhaps six CR 1/2 creatures). Here, though, consider that the Mummy has its mummy rot curse, which requires a 3rd level spell to remove - something the party won't have access to for themselves for several levels.
CR 4, 1,100 xp: Level 3
While just over our budget for a high-difficulty encounter at level 2, we're actually at only around half of what the encounter budget for 3rd level characters would be, which is 2000 (yes, it doubles at this level, perhaps reflecting the influx of power from choosing a subclass). A Lamia, as an example at this CR, is hitting relatively hard for a 3rd level character, but is actually pretty unlikely to down someone in a single hit (doing 14 damage on average per hit).
CR 5, 1,800 xp: Level 3
While our Lamia might have needed some help, something like a Troll is going to be a really significant threat to 3rd level players on its own. (Though technically it could fit a CR 1 ally to further trouble our party).
CR 6, 2,300 xp: Level 4
Much as the Troll nearly expends the entire high-difficulty budget for level 3 characters, the relatively small bump to the per-player budget here means that we're actually only 200 xp shy once again of hitting that ceiling. Here, we might have a dastardly Ghast Gravecaller, which confounds the party with conditions rather than outright power.
CR 7, 2,900 xp: Level 5
This is a pretty massive leap, as our budget per-player more than doubles now that the party is in tier 2, with extra attack, 3rd level spells, and such. Despite a jump in xp for our CR 7 creature, our actual full budget is now nearly twice what a CR 7 creature is worth, so if we want this to be high-difficulty, we'll have to make up a deficit of 2,600 xp, even if we're using something classically scary like a Young Black Dragon. Consider, though, how powerful that breath attack is - dealing an average of 49 damage on a failed save. If you're playing, say, a 5th level Bard who has, say, +2 to Con, you probably have 38 HP at this level. So, that dragon on top of, say, a Troll (unlikely given the Troll doesn't want to hang around with all that acid damage, but you get the gist).
CR 8, 3,900 xp: Level 5
Yeah, that leap in power that comes with hitting level 5 opens up a lot of potential foes to fight. Here, we can apparently still fight a Chain Devil with enough xp to spare to have a CR 4 ally for them.
CR 9, 5000 xp: Level 5
Damn, guys. Again, as a reminder, we're talking about high-difficulty encounters here, and I would not recommend sending a Clay Golem after your party several times in a day after they had just hit level 5. Still, this is in-budget and has enough for a CR 2 monster left over.
CR 10, 5,900 xp: Level 6
Finally we hit something 5th level characters just shouldn't try to fight. Something like a Yochlol demon is now pushing us beyond the mere beginning stages of tier 2, though again, we've got enough left over for a CR 4 ally.
CR 11, 7,200 xp: Level 7
Ok, we're now blowing through to a new level. I do think that as we hit CRs 10 and higher, we're starting to get into the range of monsters that can remain relevant all the way to level 20, even if what is now a dire, deadly encounter would serve better as a minion to some tougher boss later on. A Remorhaz can swallow PCs and pump out a lot of damage, with an attack bonus that should hit pretty consistently even against heavily-armored foes.
CR 12, 8,400 xp: Level 7
Still in this level range, a CR 12 monster is coming very close to fully expending our xp budget, but it means that a party of 7th level characters (like my Wizard, whom I've been playing for over three years) could take on something like an Arcanoloth... though it would be a tough fight.
CR 13, 10,000 xp: Level 8
As a note, I'm ignoring the "in lair" version of creatures here, but if we accept that, this means that 8th level is the lowest a party of 5 can be before they can face off against one of D&D's most iconic creatures: the Beholder. (And here I was always thinking that you'd have to be tier 3 to get there).
CR 14, 11,500 xp: Level 9
Now, we're starting to hit a point where, at least in the Monster Manual, the number of creatures at any given CR is diminishing. Here, I'm looking at the Ice Devil as an example - a relatively simple creature that might make more sense as an elite minion at higher levels (though it can cast Wall of Ice, a fairly complex spell).
CR 15, 13,000 xp: Level 9
This, it turns out, is precisely what the high-difficulty budget for a group of 5 9th level players is. So, if you want to give them a hard but theoretically winnable fight, you can throw a Purple Worm at them.
CR 16, 15,000 xp: Level 10
This isn't quite as perfectly precise, but it's only a little below the full budget for 5 10th-level characters. Thus, if you want a really hard fight near the end of tier 2, an Iron Golem is technically an acceptable choice.
CR 17, 18,000 xp: Level 11
I may have screwed up the math in my analysis of the Death Knight as a potential boss at the end of tier 2. In fact, this, or the new Dracolich (outside its lair) will generally be considered overkill until the party reaches tier 3. Armed with 6th level spells, or some features that really enhance player power (like Radiant Strikes or the Fighter's third attack,) the party can take on either of these undead menaces - though it's going to be a really tough fight. (I might have been budgeting for a 6-player party, actually. That would explain it.)
CR 18, 20,000 xp: Level 11
Truly filling nearly our entire budget, we only have one example of this CR in the Monster Manual, which is the Demilich.
CR 19, 22,000 xp: Level 12
Again, only one example here, and it nearly fills the entire budget, we have the toughest demon in the book, the Balor.
CR 20, 25,000 xp: Level 13
At CR 20, we're now getting into levels where most of what we find are legendary monsters. Here, we get the first of the Ancient Dragons, such as the Ancient White Dragons. Given how a lot of campaigns only go up to level 12-14, it's fitting that at least we can start facing down these most epic of monsters.
CR 21, 33,000 xp: Level 15
That's interesting: we have to wait two levels before we can actually get up to CR 21 monsters, including another of the most iconic creatures: the Lich. Given how iconic a Lich is, it's interesting to think that only characters of a level few ever reach are considered ready to face one (though the 2014 one was kind of pathetic and could be taken out in a good turn by a Fighter or Paladin, so their mystique suffered a bit).
CR 22, 41,000 xp: Level 16
Yes, we're hitting the end of tier 3, and it's only at this point that we can face down one of the new Titans, the Elemental Cataclysm. Note that it's hard to find creatures at this level that aren't ancient dragons.
CR 23, 50,000 xp: Level 17
While 16th-level characters are only just shy of hitting this with their budget, apparently now that we're getting into the truly globe-shaking monsters like the mighty Kraken, we've got to get into tier 4.
CR 24, 62,000 xp: Level 18
A mere 9th level spell is apparently not enough for you to face the deadliest of all the Chromatic Dragons, the Ancient Red Dragon, as you'll need to be level 18 before you fight one, in theory.
CR 25, 75,000 xp: Level 19
We're running out of monsters, with only the Colossus at this CR, and only one more monster in the Monster Manual to look at. And, evidently, such a creature is meant only for a party that is on the cusp of achieving their ultimate power.
CR 26, 90,000 xp: Level 20
Now, I'm cheating, because we're going outside the Monster Manual and looking at Demogorgon, the Prince of Demons, the Sibilant Beast. Yes, according to the encounter-building guidance, you don't want to face the giant two-headed baboon that wants to and actually could destroy the universe until you're level 20. Does Monsters of the Multiverse live up to the 2024 standards of monster difficulty? I'm not sure. I will say that I ran a one-shot in which the party fought Orcus (also CR 26) at level 17 and did fine, so color me skeptical.
CR 27, 105,000 xp: Level 20
The Chromatic Greatwyrms from Fizban's are technically doable for a party of 5 players, but this cheats slightly because they're mythic encounters that in theory should be worth double their XP - and thus be officially beyond the budget for any party of less than 10 20th level characters.
CR 28, 120,000 xp: Nobody
Yes, we've now hit the XP level where 5 players, no matter how high-level they are, is actually supposed to be able to fight something as powerful as Sul Khatesh or Rak Tulkesh, or a Chromatic Greatwyrm. Notably, the former of these is infamous for being basically unkillable, as she can create four massive anti-magic zones that don't affect her own spells, and she cannot be harmed by non-magical weapons (which, notably, any weapon becomes when in her zone). So, you basically can only harm her with an artifact, and even then, she has at-will Shield, which gives her an effective AC of 27.
CR 29: ???
I don't think there are any CR 29 monsters in all of 5th Edition, but presumably they'd also be in this category.
CR 30: 155,000 xp: Nobody, But More
Yes, in theory, the Tarrasque is too difficult for any party to face. (I'll note though that I think the hardest fight I can imagine running would be the Aspect of Bahamut, also CR 30, if he's accompanied by the polymorphed seven ancient gold dragons he tends to travel the material plane with, given that even when those insanely powerful dragons are killed, he can restore them to full HP with his breath weapon. Good thing he's a good-aligned deity.)
Now, obviously, there would be little point to having such powerful monsters if they didn't think you could ever fight them. Powerful magic items and clever strategy can make up for the raw power these creatures possess (though the old "just have a Clay Golem fight the Tarrasque" strategy won't work anymore). Also, allied NPCs can help balance this out as well.
There's no specific guidance as far as I can tell on how to adjust an encounter's difficulty when the party has help from other creatures, but my general rule of thumb is to simply add the NPCs' xp value to the total budget - thus, if we wanted, say, a group of 6 18th level characters to fight the Tarrasque (er... no one in my group reads this blog, right?) the 85,200 xp budget I get from them is still shy 69,800 xp, but if we sent 6 Warrior Commanders (each worth 5,900 xp, for a total of 35,400) and 9 Berserker Commanders (each worth 3,900, for a total of 35,100,) we actually wrest that CR down into theoretically manageable territories (even if those Berserkers are going to still have to roll an 18 or higher to actually hit the monster).
This list is not perfectly scientific - among other things, it assumes a party size of 5, when your party could be fewer or more. And, again, at most levels, ignoring these insane super-high-CR monsters, most fights you run will probably involve multiple monsters, and multiple kinds of monster. In tier 1 and even early tier 2, don't ignore those less-than-1 CR creatures, who might be individually pretty weak but in the massive numbers you can start to have with them, can still be quite a threat.
Essentially, this exercise is primarily to be for DMs who are champing at the bit to use some cool new creature that has inspired a story in their minds.
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