In Dungeons & Dragons, a party without a rogue is like a sky without stars. Sneak attacks, high stealth checks, and locked doors no longer plaguing your adventurers are a few conveniences the rogue class brings to the table. Pair this with the many roguish archetypes your character can take, and the rogue ends up with numerous handy and colorful play styles.
Yet the pitfall many players deal with, and one the rogue class is known for, is coming up with a unique backstory that doesn't just write the rogue off as a street urchin who learned their thievish tricks from the school of hard knocks. If you're looking for some variety where your rogue cut their teeth, you needn't look further.
6 Trained Weapon
Your character was taken from their birth parents and raised within the confines of an elite assassin training facility. You never knew your family to be anyone but your fellow operatives, and any trace of your former life, perhaps even your existence, has been taken from you. As a result, you're a calculated, cold killer without remorse or doubt; you're whomever your current job requires you to be.
This background could easily fit the Assassin archetype, doubling down on how deadly you are when the battle conditions are in your favor. Immediate things to develop are your codename or details on the organization that trained you, but other things to ponder are the life you would've had if it hadn't been taken from you. Has playing nice among other adventurers softened you, arousing a desire for "what could've been?" Or is one of your adventuring companions simply your next target?
5 Wizard School Dropout
At your noble family's behest, you trained day in and day out at the local wizard college, studying incantations in forgotten languages, learning the fundamentals of spellcraft, and all the rules and regulations of when you should and should not use magic. And if that didn't bore you to death, the life you returned to when school was over was stuffy and strict. When you dropped out, your family took it hard and cast you from your own home, hoping your actions wouldn't tarnish their political standing. You're back to square one, with a lot less to your name, and you couldn't imagine a better situation.
With some arcane education in your past, the Arcane Trickster is a perfect choice for this backstory. It blends the magical upbringing with the skills you've picked up to survive, even adding some humor to your character as to how they've utilized their talent through the Mage Hand Ledgerman class feature. But maybe you decide to take the route of magical ineptitude, in which the Thief subclass even implies some trouble-making in your school days. Think of referencing characters like Ferris Bueller for the kind of lightheartedness this story suggests.
4 Private Detective
You started as a city guard, but the paycheck was much easier than actual justice. The kingdom's system of law is corrupt from top to bottom, and the streets won't stay clean unless the people that walk them roll up their sleeves and take problems into their own hands. That's why you hung up the uniform, so you could join the masses and blend into the sea of faces. The criminal underworld runs deep; taking out the trash is like moving a mountain. You lop one troll head off, and two more take its place, but that's one more head than you ever saw roll when wearing "the badge."
The hard-boiled detective is a fun trope that doesn't always get a chance to play in a high-fantasy setting. Still, those familiar with the Eberron campaign setting would say otherwise. Previous occupations for this character could and should relate to something in line with the BBEG or an organization that serves as an antagonist to the adventuring party (and let's face it: city guards are always against a group of adventurers.) The Inquisitive background takes on a "Sherlock Holmes" archetype, becoming a master of perception and investigation, even using it in combat to analyze an opponent's fighting style to exploit openings, fitting perfectly with this characters calculated outlook on life.
3 Crossing The Threshold
Life in the country is quiet and straightforward, something you've come to loathe with each passing minute. There's always something that needs doing around the family farm, and there's seemingly no end to the cycle of responsibility. The freedom of "choice" isn't something you've experienced much, so the day you made your first one was the same day you left, and you haven't looked back. Toiling away with the hard labor of farm work and the practical skills of hunting for food have sharpened your survival senses, and you've used every bit of that knowledge to carve out your corner of the world.
A young character in Dungeons & Dragons is fun to play, as playing up the naivete and bravery of someone who shouldn't be able to beat the odds, yet always seems to do so, can be endearing. The Scout blends the naturalism of a traditional barbarian or ranger with the rogue's slippery and cunning tricks. Reimagining the rogue's abilities like Evasion and Sneak Attack with the lucky opportunism that comes from a youth thinking fast on their feet makes for a pretty wholesome, charming character.
2 A Life Of Service
The kingdom's last war was bloody and drawn out. The hard-fought victory meant peace, but peace isn't lasting by nature; it must be carefully kept by those willing to serve long after the battle's end. Your capability on and off the battlefield was recognized time and time again, and, as a result, you're now a key player in maintaining the nation's post-war relations. Are you a soldier? Always. Are you a politician? When the job calls for one. Are you a hero? Some might say if they even knew you were still alive.
Rogues are just as capable in combat as a Fighter. Still, the idea of a former or current soldier often passes to the ladder, typically leaving rogues with the implication that their training is somehow less formal. What's more interesting is imagining how a Rogue's unique abilities are a specialization within the military and how that might've influenced your character's career during and after a war.
Taking the Mastermind archetype not only affords you some team-based combat abilities, implying training within a unit but awards unique bonuses of spy-like qualities in analyzing a target's behavior and capabilities, as well as being skilled in the art of deceptive conversation and interrogation.
1 From The Shadows
Overlapping with our world is another almost identical in design but starkly different in virtually every other way. Wreathed in shadows, blanketed in darkness, the Shadowfell folds around the Material Plane, and only death and decay await unsuspecting visitors. Here, the trade of rogue is commonplace, and the skills one mortal may develop in this macabre world are far beyond what a commoner considers normal.
Perhaps you are a careful Barovian who has slipped past Straud's watchful eye and escaped his Domain of Dread. Maybe you are a follower of Mask, the deity of shadows and Master of Thieves. Whether you work for yourself or the ends of another, your business in the Prime Material means you're surely up to no good.
The Shadowfell is a place of potent necrotic energy, so if you're looking for the framework for a truly edgy assassin, this is precisely where you should start. You could be a devout follower of a dark god or a creature born entirely of the shadows of others, crafted with only the purpose of bringing death to others.
Several haunting backgrounds are presented in Van Richten's Guide to Ravenloft that can take the average human and elevate them into something dreadfully mysterious, everything a classic rogue strives to be.