One way to choose is based on difficulty. It's true that some classes are harder to play than others, and there's good sense to playing a character whose challenge level to play matches what you want. A pure spellcaster like the Sorcerer, Warlock, or Wizard takes a more developed understanding of the game to pull off and enjoy than most beginning players are capable of to start. On the other hand, a Fighter can be a much easier introduction to the world of D&D's combat, vital statistics, and game rules without additional systems to learn. In the ratings below, I will rank each class on a scale from 1 to 5 where 1 is easy to pick up for beginners and 5 is a more veteran challenge.
Another way you might choose is based on what kinds of actions you'd like to be able to take. After all, playing a stealthy rogue and playing a rowdy barbarian are pretty different experiences. To that end, I've provided a short paragraph about the kinds of exciting actions that the class is capable of. These observations will be drawn from a combination of my own experiences playing these classes and my consideration of players playing those classes in games I have DMed.
You might also be interested in knowing what specifically you'll need to learn in order to be effective with the class. If your character's survival being based on your understanding of how to manipulate rules makes you uncomfortable, there's a whole list of classes (spellcasters in general, clerics in particular, and rogues) that you'll want to avoid since mastering the rules is a core part of these classes. In order to express what types of things you'll need to learn, I'll provide a list of the types of ideas you'll need to learn.
And finally, you may want to know what role the character will fill in the party. Now, it's worth noting before going any further than any class can have any personality, so if you're worried about roleplaying, make your choice on type of action primarily--class doesn't dictate personality. But if you know you prefer to be a support character or want to be one to serve the character idea, you have options (cleric and bard, most notably). There's a role for everybody, but it's important that you enjoy filling yours. I'll provide a brief analysis of the roles you can easily step into with each class.
So, based on these four categories of information, I hope to help you find the best class to start with. Let's begin.
Barbarian
Difficulty: 1
Actions: Barbarians are best known for their ability to enter Rage, a state in which they are more likely to strike in combat and do more damage, also gaining hit points. Barbarians are a standby for combat-oriented players; this class gets the most health of all classes and can reliably deal among highest damage in melee. Every single special ability granted to barbarians revolves around being more effective in combat, including bonuses to initiative (how quickly your character acts in combat), extra attacks, and resisting damage.
What to Learn: Tactics. As a barbarian, your greatest strength is combat; you can either be good at it or truly great at it. Without tactics, you'll do well, but with careful attention paid to maximizing your strengths, you'll destroy everything your DM throws at you. This also means getting familiar with the rules that govern your abilities.
Role: Barbarians are usually tanks--hard to kill and good at killing. It would be possible to develop a barbarian into some other role, but the task would ultimately ignore that this class is meant to be a combat machine and little else.
Bard
Difficulty: 5
Actions: Bards have a wide variety of abilities. They are capable of magic, have immense bonuses to skills, and are able to help allies succeed. In simple terms, bards are built for support, but are kind of a mixture of all the classes in the game--they're capable of combat, magic, and skills. Bards are not necessarily masters of as many things as they are strong in, so thinking on one's feet is usually another part of what bards need to do, especially since they usually function as the leader of the party.
What to Learn: Everything. Because bards can do magic, combat, and skills, they need to learn the rules behind each of those skills. But knowledge of rules and mechanics won't be enough--you'll also need to learn to be a good support player and use your spells and class abilities in a way that actually helps your fellow players.
Role: As with their abilities, bards can be anything. Charismatic and clever bards lead parties and entertain crowds. Tactical bards turns the tides of battles with buffs and healing. Sagely bards become expert spellcasters. You can be anyone as a bard.
Cleric
Difficulty: 5
Actions: Clerics are the only class in the game given the full suite of healing abilities. Other classes (bards, druids, and paladins) are capable of healing spells, but clerics are specifically made to do so. This means every party could use a cleric, though they're not easy to play. Aside from healing, clerics can also fight undead, cast a huge array of spells, and specialize in an approach to magic that grants special abilities and extra spells (a domain). At the same time, clerics are equipped to be effective in combat.
What to Learn: Magic rules to start. The cleric's skill as a melee combatant are relatively straightforward (tactics help here), but they're mostly important as a healer and support character, so being very familiar with which spells do what and when is very important. Knowing about the other player characters in your party is also important so you can better support them.
Role: Clerics are great as a healer and support unit, but since their spell list is pretty broad, they're capable of quite a lot. It's worth noting that a cleric alone can be formidable, but a cleric with someone dangerous is greater than the sum of the parts, so be ready to work as a team.
Druid
Difficulty: 4
Actions: Druids get several exciting abilities. The most famous is the ability to turn into an animal (Wild Shape), but they can also choose specific "circle" to belong to, meaning a specific region held dear by the druid. These circles are similar to cleric domains, granting special spells and extra abilities. Druids are able to cast magic, and they have fairly diverse spells, making them capable of quite a lot if they're creative about it.
What to Learn: Mostly magic. Druids are largely defined by their spellcasting abilities--they are not bad at melee fighting, but their strength is in their magic. Once you've learned magic, the only major complication is in the Wild Shape rules--it can be tricky to keep track of which abilities you have in which form during a tense moment.
Role: Druids are fairly powerful spellcasters whose magic tends to disrupt combat and swing things toward the party. This means that they're direct presences in combat, but standing outside of the fray. Druids are also good guides since they can navigate nature so well.
Fighter
Difficulty: 1
Actions: Fighters' abilities, like barbarians, are almost entirely focused on combat. With the exception of the Eldritch Knight archetype, the abilities are all focused on making more attacks, doing more damage, and surviving attacks. The Eldritch Knight adds spellcasting to the fighter, but only in the form of protection and damage spells, so the effect is ultimately the same. Notably, the fighter gets to choose a fighting style which grants bonuses based on specific tactics in combat.
What to Learn: Tactics. Most fighters tend to fight on the front lines, hoping for high rolls against enemies, so knowing how and when to move around the battlefield is a vital way to make the most of your abilities.
Role: Fighters are invaluable as tanks. Since players tend to make fighters with the intention of focusing on combat, I've never seen a fighter used for some other role. In the hands of a sufficiently-committed roleplayer, I'm sure you could see a fighter party leader, but mostly fighters are fighters.
Monk
Difficulty: 2
Actions: Monks are martial arts experts on the surface. 5E has done a pretty satisfying job of coming up with special martial arts combat rules for monks (including different schools of martial arts), and most players who came for ninja-ing around leave happy. Monks also have a variety of very special abilities that help them transcend the laws of reality, which is very fun. But on top of this, monks have a great many special abilities that depend on selection of a monastic tradition, and they range from combat approaches to stealth applications to magic mastery.
What to Learn: Kind of a lot, surprisingly. You need to learn the base game like anyone else, but the monk rules replace basically all of those rules (but learning them first wouldn't work because there'd be no foundation to start from). I mentioned lots of special abilities--if you don't use those abilities and use them well, you end up being just a watered-down fighter. So get used to the rules and the special monk variants.
Role: Monks are a strange class in this way. On one hand, monks can be incredibly strong in combat. On the other, they can fill a lot of the same roles that rogues do (stealth expert, specialized attacks). And monks can even be leaders given their wisdom--it just depends on how you play it.
Paladin
Difficulty: 3
Actions: Paladins are basically a halfway point between clerics and fighters (basically). You get plenty of strength in combat, plus some magic and a dose of healing. Most of the special abilities of paladins revolve around improving their abilities in combat, and the special oaths that paladins take let you decide between justice, nature, and vengeance as inspirations for more abilities. In essence, a paladin is a fighting character with the ability to add some support.
What to Learn: Like with the cleric, paladins demand that their players learn to operate tactically in combat as well as the basics of spellcasting. Fortunately, the rest of the paladin's abilities function much like the fighter's, so simply focusing on tactics and magic will allow you to do well with a paladin.
Role: Paladins are interesting in terms of role--they can act as tanks, as minor healers, and as party leaders (especially since their magic is fueled by charisma). It really comes down to what the party needs and how you want to play your paladin.
Ranger
Difficulty: 3
Actions: Rangers are specialized combat classes as a foundation--they get special fighting styles, combat bonuses like extra attacks, and strength against a chosen type of enemy. At the same time, they get access to a range of spells and extra abilities that grant nature-based boosts and magic. They get the paladin's same abbreviated access to spells (level 5 maximum as opposed to a sorcerer/warlock/wizard's level 9 maximum), most of which are useful in the wilderness or in combat.
What to Learn: I'll say that like all combat classes, tactics are useful here, and that like all classes with magic, learning the magic rules is useful. I'll add, though, that rangers are perhaps the easiest classes with magic to pick up. The shortened spell list and relatively straightforward spells are less intimidating than other lists, and the combat abilities are comparable to the fighter list. This could be a good first spellcasting class for a beginner.
Role: Rangers can be a few different things easily: they can be tanks or strikers depending on the build. Some rangers can be stealthy, and others are practically barbarians. A ranger can be almost anyone so long as there's a place to be filled.
Rogue
Difficulty: 2
Actions: Rogues have probably the most diverse and customizable foundation in the game. They're given formidable combat skills (sneak attack, uncanny dodge), broad subclasses (or "roguish archetypes" such as stealth, combat, and magic), and a load of powerful abilities that apply in many situations (evasion, cunning action). I've seen and played rogues who were assassins, con artists, thieves, and mages. For beginners without a clear sense of what you want your character to be, the rogue can present so many options as to be overwhelming, but the rogue can also be a great way to make an interesting non-combat character who can still hold their own.
What to Learn: Basic tactics will help you figure out how to use sneak attack correctly. Beyond that, you basically just need to keep your many abilities straight. Rogues have lots of abilities that only happen in certain conditions, and remembering all those details is probably the hardest part of playing a rogue.
Role: Rogues can be, more than any other class, any role at all. A rogue can be an aloof and arrogant tagalong, the charismatic heart of the group, a brilliant expert, or the hilarious goofball--and all at once. The customizability of the class means it's open to your imagination.
Sorcerer/Warlock/Wizard
Difficulty: 5
Actions: Let's clarify something: I'm placing these three classes together, but they are not identical, and they have different specifics when it comes to abilities. I am placing them together because, from the perspective of a first-time player, they are basically the same enough that we can talk generally about them. Now, these classes are entirely about spellcasting. That means that you have no combat abilities and few skills to back you up--your spells have to speak completely for you. So not only do you need to juggle dozens of spells, but you need to be fluent with using them, or you'll end up without remaining magic and be in trouble. If you're getting started with a magic-centric class, feel free to check out my guide to learning the rules of magic.
What to Learn: The magic rules. This will, in turn, lead you to need to learn most of the rules of the game. Any given spell might reference two or three rules, so knowing the rules and how they fit together really helps with understanding spells. I'd also recommend paying attention in-game to how fights unfold so that you can use that information to your advantage when casting magic.
Role: Here's where things get especially hard to summarize. Wizards are fueled by their intelligence, so they often work differently in-game than the charisma-driven sorcerers and warlocks. Further, these two latter classes have different sources of magic, further characterizing them: sorcerers are inherently magic from their very blood, while warlocks have made a bargain with an elder god to obtain their powers. You can imagine that details like these might affect your game if story is concerned. In broad generality, though, spellcasters operate as strikers, doing considerable damage and turning the tides of battles. They can also be party leaders, especially the more charismatic of the bunch.
That's the overview. Hopefully you have an idea of what class you'd like to play. If you have questions or just can't decide, I highly recommend talking it over with your DM. They can help you understand your choices in the context of the campaign you're playing, and they might steer you towards something that serves the game well. What matters most is that you have a sense of what you're getting into--D&D can be a lot, and going on with your best foot forward can help you find your fun.
That's all for now. Coming soon: religious beliefs by cultural group in my homebrew setting, a dark time-loop adventure in an original system, and profiles on the major cities in my homebrew setting. Until next time, happy gaming!
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