Interlude: Don't Use Character Generators (Except When You Should)
These days, I run about 90% of games in an online setting. One of the reasons I prefer this (apart from having a substantially larger pool of potential players) is that I can take advantage of a lot of tools or practices available to me when I'm at my computer that I can't really utilize at a physical table. Instead of scribbling notes on paper I can keep track of PCs and foes and various other things on a Google sheet, Discord has a great dice roller bot, and I like being able to keep the PDF open in different tabs along with other things I might need to facilitate running the game. There are also usually a number of web tools that people have built for the various indie games with incredibly vibrant communities, like Mörk Borg or Cairn or Mausritter and such. One of these tools are automatic character generators, and I've started to have very mixed feelings about them.
On the one hand, these character generators are really fucking cool and are generally well-polished and easy to use. But I think that they have a very specific use case; sometimes doing it manually is still important.
When Not to Use Them
I think the strongest argument for this point is that you absolutely should not use a character generator if it is the very first time you've ever played a particular game and you are trying to learn it. For many systems, I find that actually going through the steps and building a character helps you learn how the game works. Even if the procedure doesn't set out with that as the intention, often just seeing each part of the process one at a time helps to give you a basic understanding of what constitutes a character.
One example of this is found in Wolves Upon the Coast. Character creation is the very first thing you read in the rules, which I find to be notable because characters are put front and center in this system-- the main thrust of the game comes from characters growing in power and renown through their actions. Following the process step by step introduces you to game concepts-- the three characteristics provide bonuses to certain rolls or saves, and you are then shown what these saves are used for. Next, you learn how the wearing of different types of armor impacts the saves you just learned about.
The next section details what your character starts with-- equipment, hit dice, attack bonus, languages, and most importantly, a ship that is shared with the other players. This single page of the rules presents a world where PCs must rely on their physical prowess and their equipment to succeed; a cosmopolitan world where many different cultures interact and trade; a world where success depends on cooperation with your companions.
Finally, lists of weapons, armor, and equipment complete the introduction to the game. Weapons have special effects, implying that a smart and strategic approach to combat is important, and the armor and equipment flesh out the setting in terms of what would be available. Automating the part where you're choosing your equipment eliminates any opportunity for strategy, and if you don't look at the weapon list, you won't see what the various options for special properties are.
Another brilliant example of how equipment obtained through character creation gives life to your PC can be found in Cairn 2nd Edition. It takes the importance of starting equipment a bit further. When you choose or roll for a background, there is a list of automatic starting equipment that is thematically linked to the background. Additionally, there are two tables for each background that combine interesting life events with some sort of specialized equipment. They are typically framed as a question about something that happened in the character's past, with the table result as the answer. These tables can completely change the concept of a character, and I've run games where two players made characters with the same background that ended up feeling entirely different from each other. It also really brings home the idea that your capabilities in Cairn are directly tied to what you are carrying with you. Following the (very short!) procedure step by step allows you to see how your character is coming together, and you can begin to flesh out the life events that led you to this adventure.
The automated versions I've seen of these at least include the "question" part of these background tables, so you're still getting that bit of detail. However, it's also literally just two rolls-- this isn't a huge time sink. Just put in the minimal effort and enjoy the process!
When You Should Use Them
Now, all that being said, there are definitely times when character generators are useful! The obvious one is when you've already learned how to play the game and made several characters and understand the parts that go into playing a particular system. Sometimes it is nice to be able to make a new character in a couple of clicks, and you don't need to follow the steps to be able to effectively bring the collection of numbers and words on the paper to life.
Generators are also nice for preparing for a convention game or a one-shot, if you're in a hurry. Sometimes it can be nice to sit down at the table with a mug of coffee and a stack of blank character sheets and spend a relaxing afternoon rolling up pregens, but when time is an issue there's no better use for a digital generator-- especially since many of them have print functions.
Another time that a generator is useful is when you're playing a game that expects there to be a fair amount of PC churn. One of the common features of games in the OSR-adjacent space is that character creation is quick by design. The implication of this is that you're supposed to be able to make a new character very quickly so that you can get back into the action when the previous one dies by misadventure. Similar to the first example, if you're already fluent in how the game works, you don't need to go through the exercise every time, even if it is significantly quicker than creating a new character in something like D&D5e or other crunchy games loaded with character options. I've lost count of how many incredibly fun Mörk Borg sessions have churned through a dozen different PCs in a single session, with the players clicking the fated button on scvmbirther
In Conclusion
Character generators are useful, except when they're not. They're good when you are already very familiar with the game and want to save time. Ultimately, do what you want, I'm not a cop!