Scoundrel Character Concepts| Player Character Inspration | D&D | TTRPG | Web DM

[@WebDM]

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[@MrRhexx]

What's interesting is that my scoundrel player can get away with doing so many morally grey things that nobody else on the party can get away with, but at the same time whenever they do a good deed it just feels more genuine than the rest of the characters because of the contrast.

[@WebDM]

Absolutely! They tend to be so relatable and easy to root for. Thanks for stopping by!

[@epileptictrees5213]

Odysseus is a great example of a classic trickster/scoundrel character in that he uses his wits and charisma rather than raw power.

[@MrDavidKord]

Despite the fact that he has raw power. AND he defies death multiple times. Good one.

[@AGrumpyPanda]

Most Greek heroes are tricksters on some level, even Heracles was tricksy and cheatsy with a lot of his labours. Odysseus just stands out because he was all tricksy all the time.

[@EricVulgaris]

Dude is so suave. Half the odyssey is him showing up on a beach looking like butt, takes a shower and comes out looking like an 11/10.

[@derekstein6193]

The original Death-defying scoundrel, King Sisyphus. Tricked and bound Thanatos; Death incarnate. Zeus had to sent Aries to free the god of death. Sisyphus also set up, in advance, a means to convince Hades to actually allow him back to the land of the living for a day (spoiler; he took a lot longer). And finally he survived to old age and went willingly with Thanatos to Hades. He went to the afterlife on his own terms. The only reason Hades forced him to push a boulder uphill forever in Tartarus was because the Olympians were generally petty jerks and they were just salty that a mortal outwitted them.

[@tannerharmon2325]

I haven't been this early since Jim was the one with the beard.

[@jmvh59]

Word

[@CrimsonWolfe776]

This hit me harder than it should’ve. Feels like these dudes really have been around forever 🙏🏽

[@tannerharmon2325]

@@CrimsonWolfe776 can't believe my favorite nerds have been around for 6 years

[@WebDM]

It's true, 6 years on KZbin is a very long time. Thanks y'all.

[@tannerharmon2325]

@@WebDM To another six!

[@Calumba1904]

My favourite Outlaw Noble is Lelouche from Code Geass. Slacker genius prince in hiding given one power and uses it to lead a revolution. He even dresses like anime Zorro/Batman. Great character from a great show.

[@jikkepk8018]

This is right up my alley. I've been playing a con artist trickster cleric, and it's the most fun I've ever had with a character!

[@WebDM]

Right on, Esther!

[@rpeterson9182]

Ultimate cheater of death? Jack Sparrow. All the Bebop crew? Everyone except Ein. Favorite scoundrel of all time? Han Solo. 😍

[@blainewheaton9679]

The Mistborn books dealt with a sort of reverse ‘outcast noble’. There were a lot of street type scoundrels who ran heists and cons on the nobility. So by the end the characters could do that ‘walk in both worlds’ thing, but they came from the other side.

[@Neverfate]

Thieves, rogues, scoundrels and the like have been my favorite archetype since I picked up an old AD&D PHB as a little kid. I wanted to be those thieves on the cover that are prying the gems out of the statue. All the sneaking, subterfuge and guile is so appealing. It's an archetype that rewards being fast and clever rather than super strong or powerful with magics. They're the person you least expect, but they're the best of the best for their own reasons, to their own end. I'm playing two *wildly* different rogues in 5E right now and I'll play a dozen more by the end of this edition.

[@RIVERSRPGChannel]

Scoundrels can make some of the best characters

[@WebDM]

Hard agree!

[@dakotacouch5642]

My favorite scoundrel of all time is Locke Lamoroa. He's from the gentleman bastards by Scott Lynch; if you like fantasy, heist, and/or grimdark novels this is a must read.

[@jdubbs69]

That's a legendary thumbnail you guys have there, well done!

[@WebDM]

Thank you!!!

[@Fomor_Ian]

Funny how the video talking about scoundrels is also sponsored by City of Mist because I actually made a scoundrel like character in city of mist for an upcoming campaign. Eiko Yamashita is a former gangster with the mythos of Izanami who was left for dead by her ex-lover during a heist gone horribly wrong. The mythos revived her into her new undead rotting form and when word got out that she had survived, she was made to take the fall for the entire operation. Now, she’s working as a bounty hunter on the low while out for the blood the organization and man who wronged her. Can’t wait to play her soon

[@WebDM]

Awesome!!!

[@coreygardner9803]

"a scoundrel by perception." All I can imagine is the reverse cliche of the classic rogue. Loving family, great values, never steals, and wears a black cloak his grandma made to keep him warm. Yet he still looks like the edgy guy brooding in the bar.

[@docnevyn5814]

That supershady Strider guy smoking a pipe in the shadows with his hood up inside the Inn? Oh you mean the Rightful King of Gondor, Aragorn?

[@Overlord99762]

I made a half elf that sort of fits this, but he DID steal, but only from assholes who had wealth but no compassion and his ill-gotten loot went straight to the pocket of his siblings and his widowed father

[@ItsJensik]

How do they talk about a bargainer and cheater without mentioning Captain Jack Sparrow? It's all he ever does.

[@grimrider3807]

Hey I just wanted to thank you two for continuing this channel. I’m sure it’s not easy to always have a topic to cover. But I appreciate your hard work, wishing nothing but the best for you going forward.

[@WebDM]

Thank you!

[@jf649]

Same. I most enjoyed you class series (especially Rogues and Multiclassing, so much fun an great immersion!). Hence I’ve always wanted to see a characters concept series. Please do “Tricksters” too.

[@AlexanderBaird]

The beard is *ICONIC*

[@Grinnar]

Having an Inevitable come after your character, because they keep getting brought back to life is an interesting thing.

[@fizzyshellfish5439]

Big thumbs up for use of the word 'picaresque'!

[@arinmagnus]

I had a noble scoundrel character, they essentially got shipped off to live on their own because all the nobles and staff hated them for being such a scoundrel. They were a high charisma illusion wizard, this video brought back great memories from that game.

[@aleckozinski5073]

Love how at 26:27 it looks like Pruitt's hand comes to rest on Jim's knee in the bottom corner of the shot.

[@blainecrowley1134]

My favorite is the charismatic social scoundrel that manipulates others and is the smartest person, think Tom Ellis’ Lucifer or Raymond Reddington. The tv show Leverage is essentially an entire party of scoundrels of different types

[@yaldabaoth2]

I love to see a rogue who is going for the agent of the crown type of character. Medieval secret agent if you will. Any good (or evil) king will want to know what's going on in his domain. And maybe use an agent to goad a party of adventurers to make a problem go away.

[@benniek1050]

See you space cowboy... You love to see it

[@DiscardatRandom]

First anime I watched

[@bohemianprince7944]

Aye back again.! If i may be so bold to request a video idea: PACING. Started my campaign last month, and the first 2 sessions i ruined the starting boss, by rushing through cut scenes and plot points, just to get to combat. After the session i sat w/ my notes and realized i missed all the cool stuff haha, and that's what everyone came for. Don't rush. Take your time. I'd rather go too slow, than too fast. Nowww I'll enjoy your video Haha. Thanks for your great work, guys :)

[@WebDM]

Thank you for the request!

[@loozerid]

I have no idea why but this video makes me want to play a zapp brannigan type fighter.

[@WebDM]

Do it!

[@meikahidenori]

My favourite is lupin III, by Monkey Punch. Always after the money & girl, chased by the law, smooth talker, crafty and slippery and always got a heart of gold....and comical to the bone. Recently seen the new movie trailer for him and it looks fantastic (can't wait to import it)

[@ismirdochegal4804]

This video came at the right time. I was struggeling to find the fun in my Star Wars Scoundrel. You gave me some cool ideas. Thank you!

[@MrSarwat]

I've been playing discout NOT Han Solo for as long as I can remember

[@WebDM]

San Holo, got it

[@Drums_of_Liberation]

So Indiana Jones?

[@Nildread]

You know what they say: Do it like Pruitt.

[@corrosivecabal]

Locke Lamore. I love the idea of a rogue/bard setting up a portfolio of aliases, especially a hero/vigilante that would distract the big bad from the party.

[@MySqueezingArm]

Not sure if intended, but Web DM posts on Podbean a day early FYI.

[@WebDM]

Yes! Playing with timing

[@robertsilvermyst7325]

I've got a Cleric/Sorcerer combo that acts like a that playboy scoundrel, sort of like Miroku from Inuyasha. He hits on pretty ladies despite being a noble cleric who wants to do good in the world.

[@gho5trun3r68]

I think with the master thief archetype you want to think about why you behave this way. Archer is just such a good example because he has these deep routed feelings of inadequacy that he tries his best at never addressing unless he can use it to stick it to his mother. Most people are colossal cocky bastards without this feeling of over compensating for some area in their life where they feel less than everyone else. Touching on this will make your character go from a caricature to a living, breathing person.

[@markuswelander8551]

I usually play heroic characters with flaws but a scoundrel with a good mission might be fun too.

[@BrendanDonnelly51395]

I'm sending this video to my players before we start waterdeep Dragon Heist

[@CitanulsPumpkin]

The scoundrel character I'm building at the moment is a high elf, Dimir or charlatan, echo knight fighter. He'll eventually have 3 levels of hexblade with mask of many faces and improved pact weapon, and 3 levels of swarmkeeper ranger. Also all of his elf racial weapon proficiencies will be swapped out for things like thieves' tools, poisoner's kit, chef's utensils and whatever else the party needs. His pact weapons, swarm, and echoes are all themed to be extensions and manifestations of his own shadow. He's the perfect chameleon. Able to assume alternate identities at the drop of a hat, and when the charade drops his shadow constructs come out to bat his opponents around the room like a cat playing with a dead mouse.

[@jf649]

Feinting Death with deals to survive. Dean from Supernatural comes to my mind immediately.

[@dane3038]

I'm going to go listen to The Sword and then come back and watch this.

[@WebDM]

Good choice

[@snaketooth0943]

I had an idea for a scoundrel: Some guy-let's call him Josh-angers a mob boss. So, the mob boss gives him concrete shoes and ties him up with chains enchanted so that souls can't pass through them and dumps him in the river. So, Josh dies, but only slightly. Sure, his body's dead, but his soul can't movve on to the afterlife. So, he hops his way out of the river in search of a way to break the concrete shoes and free his hands from the chains, but not the rest of his body. See, if he breaks the chains, he'll die and go to hell, so he needs the chains so he can redeem himslef as an undead and save his soul so jhe can go to a decent afterlife. It's a bit steampunk for D&D, but it could work.

[@the_rose_garden01]

Man, you could combine this and the Mage video and it still wouldn't be as long as the Warrior video, lol.

[@briartv7071]

Perfect timing on this! I've been working on a goblin rogue I wanted to seem more like a mischievous adventurer rather than the generic goblin thief.

[@esbeng.s.a9761]

Why not bought?

[@stephenpatterson2860]

Been a bit since I caught a WebDm, and dang Pruitt! Sweet beard bro!

[@WebDM]

Welcome back!

[@Pandaemoni]

Another interesting take. One small thing, peculiar to me, (and the Cambridge English Dictionary): when I hear "scoundrel" I think of a person without principles who harms others in pursuit of their own goals...so that is a type of villain. I think the "loveable rogue" (sometimes a "picaro" from picaresque novels), looks like a scoundrel, but ultimately does have principles that prevent them from harming people intentionally...and that seems like the Han Solo type. I wonder if Han Solo and that one scene where he suggests he is a scoundrel (and creepily refuses to accept "no means no" from Leia pushing her up against a wall in tight space so she can't escape...hmmm, maybe he *is* a scoundrel) has altered the meaning for some people.

[@O4C209]

The best scoundrel is Cary Elwes's recurring character, Pierre Despereaux, from the TV series Psych. Spoilers He is pretty open about being the world's greatest thief, but no one knows how he does it. Shawn is enamored with how cool Despereaux is. Eventually Shawn figures out that it was always an inside job and that Despereaux doesn't actually steal anything. Shawn tells Despereaux he's disappointed. Despereaux says he could've actually done it. Shawn says no one could. Despereaux says "Challenge accepted". He's such a wonderful character with Cary Elwes owning everything.

[@flysteel288]

Hey Jim and Pruitt, I finally had a session 0 for my mish mash campaign inspired by Dark Matter, Star wars, From Software, Cthulhu and so on. And my players are super excited! I've DM'd a few one shots and even ran Waterdeep, but I've never been this excited to start playing. Thanks again for inspiring me to finish preparing! You said to keep you updated so I'll post about how session 1 goes next month

[@WebDM]

Right on!! Sounds awesome, keep us posted.

[@TheNerdySimulation]

It was touched on that the Scoundrel transcends class, and I couldn't agree more. I was trying to figure out how to play one when I finally got an opportunity to play a couple years back, but I never felt like a Rogue was actually fitting to he concept. Sneak Attack specifically was my issue because it just generally feels fitting to what I imagine the archetype to be. After some experimenting (and getting annoyed at 5e design) I eventually landed on Battlemaster Fighter. It kinda sounds weird at surface level, yet works so well with a bit of tweaking made to the fluff of your Maneuvers. Sadly I only got to play for a couple sessions, but I recommend it to anyone looking to try out the archetype outside of a Rogue (but also without spellcasting). It actually made me really enthusiastic to play a Warrior character too, something I normally find quite bland and unappealing. :D

[@rustyshackle8000]

Always wanted to play a thief based off of Garret from, well, Thief. Garrett isn't out to make a point. He isn't out to put his name down in the annals of history, or the glory of a good heist. Garrett legitimately just wants to pay his rent. He's greedy in the sense his main goal is getting paid, in the same way a salary worker may not necessarily like their job, but they do it because they sorta need to keep a roof over their head. Just an average, blue collar thief, trying to make a living.

[@matthewjennings7645]

Lately my struggle has been understanding a lazy character. Reading Drizzt, Regis is my favorite character by far. Now I read Tolkien, and so much more do I love Hobbits. I have planned a Halfling Character, Genie Pact Warlock. He didn't go to Bard College, Wizard school, or some immense training. In his comfort, he happened upon a genie vessel with whom he exchanged drinks and merry making and songs and riddles- for rarely does a genie meet one as vain as themselves. But how to actually play this character I've yet to sort out. In all of my inspirations they are pulled away into adventure reluctantly.

[@teacup_ninja]

I love this archetype! Suave, but not afraid to get their hands dirty and take risks, and mostly always fun to test their luck and skill.

[@CraigBoykin]

More character concepts please its a pretty unique youtube topic in the DND realm

[@myboy_]

Currently playing a campaign with 3 scoundrels, 1 Paragon and 1 Lawful evil. Been a fun time

[@TabPGE]

Kvothe from Kingkiller Chronicles is a classic scoundrel. Con artist sometimes and king of the thieves at other times

[@joesgotmore]

I had an idea for an illusionist wizard or Arcane Rogue with a charlatan background, with an aversion to violence. He is someone who always crosses the wrong person. Thinks he is the smartest person in the room but often finds out he isn't and has to get out of the disasters he causes. He gets his spellbook via a scam of a wizards apprentice. This leads him to discover he can improve his scams with the aid of magic. However, the master of the wizards apprentice he scammed the book from has influence and sends people to make my character pay...and not in coin. Joining the party is more a matter of survival.

[@joshuamcmillin7631]

Always been a fan of scoundrels.

[@mileslockhart8176]

I had an idea for a Divination Wizard, who's a bit of a scoundrel. He's a halfling with a gamblers background who managed to gamble away another person's full ride scholarship to a mage college. He chose Divination as his specialty in the hopes that he can use his foresight to cheat people. He is a gambler through and through, not just at traditional gambling games, but in life itself. He's always looking for the next great "risk" to take, and isn't afraid to cheat, especially with magic, in order to have the gamble pay off.

[@Drums_of_Liberation]

Hobbit Setzer. I like it.

[@HowtoRPG]

A reference to Han Solo was expected.

[@nicolaezenoaga9756]

Thanks. IT'S NOT DONE YET?!?!?! Nice.

[@TabPGE]

My fighter just recently got called out for being a scoundrel by the druid...I've never been more happy with my character.

[@WebDM]

Nice!

[@lynnkain]

My swashbuckling Diego is a two weapon welding, acrobatic, dashing rogue. Wine, women, and song...there is always a fortune to be made over the next hill.

[@Drums_of_Liberation]

Dual wielding Zorro? Niiiiice.

[@erasmus4743]

I love A Knight's Tale! Totally agree that Paul Bettany as Chaucer is hilarious!

[@jamesonstalanthasyu]

I like the return of the end credits banter.

[@DerexWolfheart]

i have a wizard who, mechanically is a wizard and a very creative one. he uses the conjuration ability to create all types of objects and then animates them. one thing he does is creat a 3 foot tall statue of a hulking metal man, and then casts enlarge to make it 6 feet tall, then animates it and casts heat metal and lets it go ham lol. anyway he is definitely a scoundril type, cheats in card games, wears a trench coat with fingerless gloves, has questionable morales and has a begrudging imp familiar that hate each other lol. i love playing him, hes like a mix between a john constantine, han solo, and rick sanchez, total asshole lol. hes a good dude deep down tho.

[@luckyace984]

Some of my favorite scoundrels include ( but are not limited to ) Aladdin, Captain Jack Sparrow , Jim Hawkins , ( treasure planet ) Han Solo ,and Baby (baby driver)

[@jacoboverstreet8553]

Pruitt’s going for that monk/ wizard multiclass with that beard.

[@arinmagnus]

This video has truly inspred me...

[@WebDM]

Sweet!

[@chrisr3570]

Talking of the noble going against the law, there's Zorro too

[@kassill3786]

1 minute in and getting a HUGE thumbs up for rocking The Sword!!!! \m/

[@samsonfgc3472]

Maybe rather than making a scoundrel character that cheats death before the game starts, if an existing scoundrel character gets killed by an attack that wasn't supposed to kill them you can give the player the chance to roleplay cheating death as a way out and avoid a death spiral?

[@krausier]

Instant like for my boy in the thumbnail.

[@egirlSkeletor]

The mistborn books are just a collection of different scoundrel archetypes

[@MrSilvUr]

Blades in the Dark, baby!

[@WebDM]

Excellent game! We've got short campaign of it over on kzbin.info

[@MrSilvUr]

Yeah! Watched some of that!

[@Overlord99762]

Man...Pruitt's beard looks great

[@Jagan_GT]

Jim was rockin that long hair

[@taltamary5588]

Blades in the Dark: the RPG of scoundrels, scoundrels and more scoundrels.

[@fistimusmaximus6576]

Just had visions of bill and ted playing twister when you mentioned playing a game with death.

[@derekstein6193]

Don't fear the Reaper! *air guitar noises*

[@timkramar9729]

I was thinking of a Twilight Zone episode where the guy played pool with death.

[@dreddbolt]

Cowboy Bebop and Black Lagoon both got some good scoundrel action.

[@rcschmidt668]

It would a good to see the two of you in the same room. ;-)

[@Er1c661]

@Web Dm, I don’t know if you guys take recommendations, but I wanted to ask a favour. I really enjoy your videos especially the world building ones, and currently I’m designing a sword & sorcery style world. I saw the low magic video, and it was really helpful, but I was looking for something a little more in depth into the Sword & Sorcery genre, and wanted to know if you guys could maybe make a video on the topic.

[@WebDM]

Thank you for the request!

[@ttprophet]

great vids doods. is scoundrel a concept for a playstyle or is it actually a background or class now? I need some context.

[@adamshulda-maui524]

Max from Mad Max is my favorite example of someone who cheats death.

[@RJ_Ehlert]

Lobo from DC comics comes to mind.

[@jamesrobin2857]

Favorite scoundrels not mentioned: Captain Jack Sparrow Sinbad ALADIN Tulio and Miguel

[@trajanfidelis]

Supportive Comment

[@WebDM]

Appreciative reply

[@tHeInEvItAbLePaRtY]

Pruitt, the beard's looking good

[@anthonynorman7545]

Pruitt is at Kratos levels of epic beardness!

[@brandonskoubo5176]

The entire crew of Serenity.

[@eliasvernieri]

"Constantine"

[@MrSilvUr]

100%

[@MrSilvUr]

"You've waited twenty years for me, Lou. What's another twenty seconds?"

[@Reynardnoir]

So...City of Mist looks great, but isn't that the core theme of Matt Wagner's comic 'Mage' from the 80s/90s? These kids. These kids don't know how I had to jury rig the Mayfair DC Heroes RPG to run a campaign based around modern embodiments of myths. *Shakes fist at these damn kids* ...Damn tempting though.

[@misterpig7739]

As soon as you said playing a game with death to survive I thought of Bill and Ted.

[@aussiefpv6780]

There seems to be a mixup with the video, you've accidentally put Jim on both sides.

[@df344]

I just think of James Franco's character in Ballad of Buster Scruggs for the "cheater of death" scoundrel

[@WebDM]

Great movie!

[@SeanBlader]

Harry Potter cheated death, but he's not really a scoundrel. The old people in "Cocoon" cheated death, and they could potentially be considered scoundrels, maybe. I'd consider the entire crew of Serenity individually in their roles as scoundrel. Even Kailey being so genuine she's way outside the norm for the crew. Sheperd Book is definitely a scoundrel of the church. Speaking of Churches, what about Vicar Max from Outer Worlds, I'd consider him a scoundrel too. From Critical Role, Scanlan tops the list, but also Vax, Grog, Jester (Trickery Cleric), Nott/Veth. The lack of Ashley Johnson being on the list is why I'd really like to see her Rogue it up next campaign.

[@timkramar9729]

Jack Harkness from Torchwood is your cheater of death. Jack of the Lantern isn't allowed to die either. The Marvel character of Deadpool. But the number one scoundrel in my eyes is Han Solo.

[@toddbailey8474]

It sounds pretty weird but I think a Tine Mage could make for a great scoundrel

[@christopherjonas-hamling9397]

First view and first comment!

[@WebDM]

You scoundrel, you've done it!

[@nicolaezenoaga9756]

Great!!

[@feelingweller]

Loki is a good example of a scoundrel who cheats death all the time

[@WebDM]

Absolutely!

[@feelingweller]

@@WebDM Every time I comment, you guys respond and it brings me life! Over the past few years, I have enjoyed the great content and the fan interaction. Here, take my patreon money!

[@TheFirelordZuzu_]

My favorite outlaw noble is Toph from Avatar the Last Airbender 💚

[@robertbemis9800]

Cheater of death “Rincewind of disk wor old”

[@willmackinnon9397]

I rarely play a Rogue, but I always play a scoundrel

[@hoki3697]

Is Jim's voice gonna make a return?