For some reason when it comes to class options Rogue has always been my least favourite, not saying it is a bad class just it feels like any cool character concept you could come up with for a rogue would be better suited to a different class leaving the standard "trained assassin" and "lowborn cutpurse" as the most common character outlines for the rogue.

That said I kind of want to challenge myself to play a class I would not normally play and with rogue being the class that I feel least inspired by I kind of want to challenge those pre-conceptions perhaps get an appreciation for the class that I did not have before.

Anyone have any cool rogue ideas for inspiration?

I once played a rogue with the noble background. He went around stealing stuff out of boredom. Didn’t even keep what he stole. Once he was away, he just tossed it aside, not because he was getting rid of the evidence, but because the game was over.

You’ve also got the skill set to be a good detective — takes a thief to catch a thief. 

Or lean more into the social skills and be a spy.

Or a scout for the military.

I've had 2 I would consider playing. One is a Soulknife who gained their psionic powers after mind flayers attempted ceremorphosis on them, they were left with a shard of power that they only recently learned to control, and they fear turning into a monster whenever they use it. 

The other is a former pro fencer who got kicked out of their league for excessive violence, and they like adventuring because there are no rules in dungeons. I'd probably go swashbuckler since it fits the charming duelist requirement, and be chaotic neutral for sure.

Inquisitive rogue / knowledge cleric... Brilliant, Sherlock-like character. Forced into the church by his family. Devout, but also a drunk and an addict. Church leaders, however, recognized his brilliance. He is trained to hunt down heretics and the church's rivals. Speaks six languages, has expertise in Arcana, Religion, Nature, Investigation, Stealth, Survival, and Insight. Very, very unlikable.

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For some reason when it comes to class options Rogue has always been my least favourite, not saying it is a bad class just it feels like any cool character concept you could come up with for a rogue would be better suited to a different class leaving the standard "trained assassin" and "lowborn cutpurse" as the most common character outlines for the rogue.

That said I kind of want to challenge myself to play a class I would not normally play and with rogue being the class that I feel least inspired by I kind of want to challenge those pre-conceptions perhaps get an appreciation for the class that I did not have before.

Anyone have any cool rogue ideas for inspiration?

 I find rogue to be the easiest class to come up with concepts for (personally):

Marvel universe: Starlord (peter quill), Hawkeye (rogue scout), Black Widow, to name a few off top of head

DC: Joker

Historical figures: Jack the Ripper, Harriet Tubman, D.B. Cooper, Jesse James, Frank Abignale, etc.

Fictional Characters: Half of Princess Bride's cast.

You could play an arcane trickster rogue, who "pretends" to be a wizard and tries to fool everyone. You could be a pacifist who's the "greatest party member you could ever hire" and is a mastermind rogue that only dodges, gets all up in melee, and "helps" his party (with his bonus action) but the second an enemy tries to walk away....*stab* sneak attack. Or, gets an order from an order domain cleric and *stab* sneak attack. You could remake half the cast of Predator.

Choices are as limitless as your imagination with the varied versatility of Rogue.

My current and favorite Rogue character so far is in the Swashbuckler subclass so it was a little easier for me to create a backstory. If you're familiar with One Piece, I base my character around Luffy. They are happy go lucky pirate that is on a mission to recruit fellow adventurers to join his crew to travel the world looking for treasure. 

It's a totally non-traditional "rogue", based on the assassin-like stereotype they usually have. But the subclass allows for that, which I think is great. I think that Rogue has a number of fun subclasses that allow you to break out of the assassin-build that is so typical. 

My very first rogue was a gnomish locksmith, who became an adventurer out of professional curiosity; he wants to study traps and locks found in dungeons so that he can replicate or improve on the designs for his business.

My last rogue (AT) was an archaeologist investigating ancient magics.  The world was one where magic was mostly banished to one island in the middle of the world, once you went to the island, you weren't allowed to leave.  My character had spent their life investigating the remnants of magical civilizations around the world before finally heading to the island for the beginning of the adventure.

One of my favorite rogues I played was a thief/spy. Yes, boring, I know, but her background was the fun part. I'll boil it down so it's not as incredibly long and confusing as I originally wrote it.

Afspyra Quill was a wealthy and well-educated professor in archaeology who took a spiral when she became much too infatuated with a certain relic she was drawn to. She did anything and everything to get it and ended up ruining her life. She ventured through an entire 7-year quest to gain the artifact and almost had it, but it slipped from her hands. At this point, she was so close to death from the quest and spiraled into addiction and became an alcoholic. She was basically thrown to the dirt and struggled to survive as she grew up middle-upper class and didn't really learn how to make a living on her own besides as a professor/researcher. Afspyra has both book and street smarts and used this to her advantage to work her way up the local Mafia-like ladder. She soon became a highly-respected and highly-wanted thief.

So, bada-bing, bada-boom: my favorite rogue ever.

TLDR: a failed Indiana Jones turned alcoholic turned thief turned Mafia boss

Common ones are: blackmailer, enforcer, fence, highway robber, hired killer, pickpocket and smuggler...and you can improve them with backstory.

Some more ideas:

Ferenge style swindler/businessman.

Thief specializing in magic items (arcane trickster) or jewels or art (thief).

Pirate (Swashbucker;  works well asautognome or warforged programmed as an assassin or spy; pirate of one of the aquatic or non breathing races for incase you wind up overboard or escape or secretly board a ship form the water)

Treasure hunter (can be a pirate or someone who finds and follows treasure maps or stories/rumors)

Spy or Ambassador (Mastermind or inquisitive). Maybe you were an ambassador of a country of city that has fallen and are now wandering. Maybe a spy who sells secrets to various powers or works for one and has specific orders as to what info he needs.

Mage or cleric killer (assassin)

Bounty hunter (if you hunt criminals who flee the city: scout). There is a background for this but you could also have the criminal background and hunt a former criminal who now hunts criminals.

You can also tie your race into the background (Spy for the yuan-ti or an elven or evil mage kingdom).

ok, that is so cool! i love the idea!! hell, you could even multi class with artificer since he wants to learn how to do more elaborate traps and locks.

Currently playing in a “Doomed Forgotten Realms” campaign, and playing a moon elf arcane trickster who was/is a Harper, a faction that is all but wiped out in this apocalyptic version of the Realms where the forces of evil and tyranny have essentially triumphed. 

The thing with rogues is that they are under powered compared to full casters and have less powerful equipment then artificers or fighters. So if your in a powerful team you could play as the badass normal. The Batman or green arrow in the justice league. Especially if you’re using a low magic subclass like thief, inquisitor or swashbuckler. 

I'm working on a rogue that is a back-alley surgeon.  Took a combat medic background and use Fast Hands to use a healer's kit as a bonus action (with Healer feat from variant human).  I'm still struggling with how the other bits fit together, but I'm liking the idea so far - but I already really enjoy playing rogues.

One weird idea I had was a Mastermind Subclass Rogue who is used to manipulating and controlling those around them, but has had everything they've done or have been doing been manipulated by the thieves guild the work for, and as the campaign goes on, they would uncover more about the guild.

That sounds interesting, but would take a lot of coordination with your DM.

My rogue wears a white dress suit under his studded leather armor.
He's very fancy for a wood elf. Owns a platinum plated wallet.
Doesn't like getting his hands dirty (arcane trickster - mage hand)
Likes to be a background character til it's time to get paid, Then and only then does he want to be a heroic adventurer.