If a system allows random generation, unless your referee is a jerk, you can usually still pick options like it's a menu if you have a concept in mind. But if a ruleset isn't set up for random generation, it's usually hard to add it back in. And if you don't have a concept before getting started, it can be easy to fall prey to analysis paralysis, or else to just making the same character over and over. Random generation provides a starting point, it tells you who your character was, before you started playing them, before they started a life as a full-time adventurer.
Random ability scores are one way to insert some randomness into character creation; random backgrounds are another. Both of those are pretty de rigueur in retro roleplaying. Most players still expect to be able to choose their own character race and character class though. (Although again, there are exceptions. GLOG players might be expected to roll for a random race, and in Jack Shear's upcoming Cinderheim campaign-starter, players roll for both a random background and a random character class.)
Maybe the ultimate in random character generation is lifepath generation. This is when you generate a random character by creating them in stages that mimic successive stages of their life. The result is not just a random character, but one who has a bit of a backstory about how they got where they are at the start of the first session. The best-known example is probably Traveller, which infamously has a lifepath char-gen system where your character can die mid-creation. (That's because in Traveller, there are no levels or XP advancement; whatever skills and abilities you start the game with is all you're ever going to get. You go through char-gen in "loops," and in each loop you get richer and more experienced, but you also risk dying. At the end of each loop, you can choose to "retire" and start playing the game, or you can continue the process. If you die though, you have to start over, so when you get a decently good character, there's a temptation to enjoy what you've won so far and stop pushing your luck trying for more.)
There's no reason, though, that you couldn't have a lifepath generator that stops with you ending up as a 1st level D&D character. In fact, there are a few that do just that, so let's look at them, and some other suggestions for generating random backstory as part of character-generation.
|2015 Gongfarmer's Almanac|
First, because of my inordinate fondness for Dungeon Crawl Classics, I'd be remiss if I didn't mention Paul Wolfe's "virtual funnel" from the free 2015 Gongfarmer's Almanac, vol 6. Like Traveller, the "virtual funnel" involves "looping" a character - or in this case a group of four characters - multiple times through a dangerous path. Each "loop" indicates an event that happened to the character, and requires some kind of save or throw to attempt.
If you fail the attempt, you take a penalty, sometimes death, usually damage, sometimes cash. If you succeed, you get a bonus, usually an ability score increase, sometimes a weapon, occasionally something magical. (If you roll well enough on the event table that "cash" is your penalty, the bonus is something really special!) And then, regardless of the outcome, you get some XP and a modifier on the roll to determine the next event. If the character dies, the next character inherits all the XP, money, and equipment received so far. When a character gets to 10 XP, they've made it to 1st level.
Good news! for Traveller fans, Paul Wolfe reports that in his playtesting, the first two characters in a group of four nearly always die, and about 1/3 of the time, all four die and you have to start over. (Pretty typical for DCC, really.) Calling this a virtual funnel is pretty accurate, since it pretty well mimics several features of zero-level play, especially the way that later characters basically get a free ride on their forebears coattails.
The random bonds, ideals, and flaws built into 5e's core rules are one method of getting random backstory, albeit one that really doesn't resemble a lifepath at all. Instead, it generates specific moments of backstory to ensure that you have three distinct kinds of moments that you can call on during play to gain "Inspiration." Inspiration is pretty much a "hero point" - you can spend it to gain advantage on a roll, or to remove disadvantage. You can only have one point at a time, although you can give it away to another character if you want.
Your "bond" is an NPC you know and care about, likely some kind of parent/mentor or sibling/friend. (Would it be worth trying to categorize and tally up the different entries in 5e's backstory tables? I really don't have the heart.) But it's also some task you're trying to accomplish for that person. The way "Inspiration" works is that you have to act on your bond, ideal, or flaw to receive it, so these entries are written to be very actionable (if perhaps overly simplistic?) Your "ideal" is like an ethical code that your character follows, or at least, one rule from such a code. Again, they're all things where it would be very easy to point out an example of your character following their ideal to show that you earned Inspiration. Like the other two, "flaws" are mistakes or mis-steps that you're encouraged to make in order to receive your hero point.
Unlawful Games suggests giving every character a goal, a kind of thing that they're looking for, not for Inspiration, just to give them some extra oomph of motivation, but this might be a pretty good replacement for ideals if you were in the market for one. I'm not sure how I feel about all this. Rotten Pulp makes a pretty well-grounded argument against offering extrinsic rewards for roleplaying. On the other hand, Dyson Logos suggests giving out Inspiration the way Numenera give out magic items - with the profligacy of a Dickensian landlord trying to ward off the Ghost of Christmas Past through a flamboyant display of generosity - to encourage the players to acquire and spend them freely rather than trying to save them up. Personally I wish that Inspiration were both more powerful and a little harder to come by. Like, it should be harder to get than just saying a catchphrase once a session, but also something that if you earn it, really does something to help you out. Anyway, that's a thought for another day.
Weirdly, 5e's recommended method of character generation almost inverts the lifepath idea. You pick a character race, then class, then set your ability scores (which are immediately modified by your race, unless you forgot since you read about that two steps ago), then finally you pick a background (and if your background skills are the same as the ones you picked for your class, then you have to go back again and select a different class skill to replace the doubled-up one.) It's really counter-intuitive.
|Xanathar's Guide to Everything|
Xanathar's Guide to Everything has a kind of lifepath generator for 5e characters. You still pick your race, class, and background, but then the generator helps fill in more backstory. There's a series of tables to learn about your family, although I find these tables to be oddly preoccupied with things like where you were born, your birth order among your siblings, and other information that feels like it's of dubious value at the table. There are tables you can roll on to find out why/how your character "chose" the background and class you picked for them, and then a life events table that you can roll on multiple times. Instead of "looping" through the table like in Traveller or Paul Wolfe's virtual funnel, you roll once to find out how old you are, roll again to find out how many events you experienced, and then finally roll on the table once per event. Your "event" is most likely to be an actual event (and then, most likely to just be "make money working your job"), with about a 1-in-3 chance you are connected for good or ill to an NPC, and about a 1-in-4 chance of some unusual experience. Some author or group of authors on the D&D Wiki has a lifepath generator for 3rd edition characters, and a 5e version that changes little, but is slightly worse. I might like this one better than the official version, mostly because it's a bit streamlined than the one in Xanathar's Guide.
This is a lifepath just for generating backstory though - it's an optional additional step after character creation is finished. Jack Shear has announced that he's working on a lifepath generator for his Cinderheim campaign that actually generates (most of) the character for you. Roll once to learn who your parents were - and thus what your background is. Then roll on a sub-table to learn another fact about your parents. Roll again to learn who your mentor was - and thus what your class is. And again, roll on the sub-table to learn an additional detail. It's elegant in its simplicity, and the subtables remind me of Into the Odd's new Bastionland careers, possibly just because that's the first place I saw something like that, and it made an impression on me.
|Goblin Laws Of Gaming|
Probably my favorite lifepath character generator though comes from Goblin Punch's GLOG rules. You generate your character in thee life stages - childhood, adolescence, and adulthood. In childhood, you roll 3 random events. Each event is paired with two ability scores, and awards a specific number of points to each. For example "You read books in the library" is paired with "+1 Str, +4 Int", while "You once destroyed a book" gets you "+2 Str, +1 Int". In adolescence, you get asked 3 questions. Each question is a dilemma that your character faced as a teen, and your answer gives you advantage rolling a dice for one ability score, and disadvantage rolling for another one. For example "Did you divide the food evenly (Int), or give the hungrier ones a little bit more (Wis)?" In adulthood, you get to roll twice on a table of random careers and then pick the one you want. You then roll four random events that happened to you during your pre-adventuring career. About half the events ask you to test one ability score to potentially improve or worsen another, and the other half award you additional starting skills and equipment. For example, if you join the army, you might get an event like "Is your scar awesome or disfiguring? Where is it?" that instructs you to "Test Con to influence Cha", or like "You are haunted by your memories. Of what?" that tells you "Learn Ghosts" as a skill.
The events in the GLOG's lifepath generator are not very specific to any particular campaign. They're less like specific backstory events and more like prompts to guide the invention of those specifics. One of the strengths here is that the generator creates a random character as you go, so that specific elements of the random backstory get tied to specific improvements (or injuries) to the character as they advance through the stages. It's entirely possible to know that you were a weak child, but your adolescence made your stronger, and you toughened up in the army - precisely because each event is tied to a specific change to an ability score.
On the other hand, if all we want is random backstory, Bardiches & Bathhouses suggests only using your class to generate it. He actually suggests using four subtables per class (double what Jack and I2TO are using) to help establish things like how you got started, what specifically you do, potentially some major beliefs, and how the NPCs in your home community feel about you. In all 3 campaign settings (Cinderheim, Bastionland, and ... Bardich-Bathhouse-land?) the subtables provide specific, evocative detail that help tie the character to the setting. If you wanted to use any of these set-ups in a different type of campaign world, you could keep the broad mechanics, but you'd need to rewrite the details. The backstory that comes from 5e's default bonds, ideals, and flaws gets around this problem by being both more generic and more vague, and then asking the player to fill in the details. It's the same way in the GLOG. Ten Foot Polemic uses a similar approach for his list of 100 retroactive backstories - the incidents described are non-specific enough to belong to almost any time and any setting, and it's up to the player add in the setting- or character-specific details.
One last suggestion that feels worth mentioning here is The Retired Adventurer's idea to physicalize backstory by tying it to specific objects, like a diary or a letter. Having that item in your inventory then serves as a mnemonic reminder of the relevant bit of backstory.
There's a partial convergence between 5e's backgrounds and its classes. Acolytes are a little like proto-clerics, criminals are like proto-rogues, entertainers like proto-bards, hermits like proto-druids, outlanders like proto-barbarians, soldiers like proto-fighters, and sages like proto-wizards. The correspondence is imperfect though. Most of the backgrounds seem like precursors to at least a couple classes, and most classes have more than one possible precursor background. And then there are the backgrounds like Sailor and classes like Monk that feel untethered from any sort of matching. (As an aside, this is probably because you have 3 "base" classes - fighter, thief, and wizard, plus wizard-thieves, ie "bards" ... plus like two more wizards for some reason, "sorcerers" and "warlocks." Then you just add on descriptors to get the others. Divine wizard is "cleric" and divine wizard-fighter is "paladin." Wilderness fighter is "barbarian," wilderness thief-wizard is "ranger," and wilderness wizard is "druid." Monks feel out of place in this system because they ARE, they are literally from an entirely different genre of fiction than any of the other characters. Although I guess you COULD probably consider them fantasy-Asian fighter-wizards.)
There's a second convergence (the one I promised up there in the title, the one that surprised me) between 5e's backgrounds and the GLOG's random careers. "Army" matches soldier, "clergy" matches acolyte, "criminal" matches ... well, criminal, plus maybe charlatan, "forest" more or less matches outlander, "hobo" matches either hermit or urchin, "nobility" matches noble, "rural" fits most of the same idea as folk-hero, "sailor" matches sailor, natch,
One final note, Bardiches & Bathhouses other post about backgrounds argues that backstory is intimately tied to character goals and motivations. He then talks through some of the most common backstories, and points out potential problems caused by some of them being pretty anti-social to try using in a cooperative game. This is an entirely different view of backstory, and one that's unrelated to the other background elements I've talked about so far. In the kind of retro-roleplaying games I'm used to, the characters might have different occupations, but they all have the same motivation - to find treasure. Empire of the Petal Throne adds a slight wrinkle to this by making all the characters barbarous foreigners trying to both make their fortune and find their way in a bizarre alien city. In Mouse Guard, Spears of the Dawn, and Mutant Crawl Classics, again, the player characters have different "jobs" but they all have the same role - that of newly-minted tribal defenders who explore the wilderness and fight off threats to their home village. The fact that one character is a glass-blower and the other's a beekeeper is irrelevant to their in-game motivation.
But 5e is a game where the player characters want different things. It's not just that one wants jewelry and one wants gemstones and one wants a magic sword. It's that one wants to help their noble family, and one wants to explore their village's hinterland, and one wants to lead their army to victory. That table of goals from Unlawful Games that I linked to earlier also introduces divergent motivations into the party. I worry a little that this is "splitting the party" at the very moment of character creation, but I would hope that most player groups can think of missions that advance multiple agendas at the same time, or else can agree to a bit of friendly "turn taking" to advance one goal at a time. I also suspect that the emergent motivations that always come up during play as a result of the players interacting with the setting will help to re-unite the party behind a common motivation.