Oregon Trail Roleplay in Red Dead Online

I participated in a one-life Oregon Trail style event in the WildRP server where people traveled on foot from Annesburg to Armadillo surviving on whatever is in their pockets.
As always, check it out LIVE on Twitch!
/ middleditch
/ tombini
Edited by: Shooklyn / shooklyntv

[@cassiar4606]

Getting shot while trying to help a horse was a fitting way for him to die. His soul was too pure for the Oregon trail. It completed his story arc

[@ryderfletcher8670]

His soul was damned on the trail. Murder. Evil. A good man can’t be evil and an evil man can’t be good.

[@pooliumm1533]

@@ryderfletcher8670a good man CAN be evil and vice versa

[@oftheHowl]

​@@ryderfletcher8670we all have both within us and it's up to us to choose our path

[@usedforks]

@@ryderfletcher8670What a tragically myopic way of looking at life

[@TheCaptainZodo]

@@usedforks It's actually an incredibly wise perspective if you actually think about it for more than three seconds.

[@KarlPHorse]

I actually really like Dewitt's character. Just a dim witted but good hearted man doing the best he can.

[@GarnachoEmpire712]

hes like wade from gta and the Sheriff is like trevor.

[@Paulshuntz]

@@GarnachoEmpire712 wouldnt say the sheriff is trevor

[@GarnachoEmpire712]

@@Paulshuntz maybe not personality wise but with his ruthlessness absolutely

[@MrGW95]

Reminds me chester or festus from gunsmoke

[@eljefe308]

The voice is absolutely perfect for the character, I can’t imagine him talking any other way.

[@virgolyx3099]

It was freaking cinematic the way DeWitt ran off after killing one of the cactus brothers, especially when he, while sobbing, tripped and fell into a patch of red flowers, almost like he had just fallen into a pool of blood he created.

[@effortlesslytalented]

Exactly it was so poetic

[@matts7125]

I didn’t even notice that!!

[@Finn-wc8nq]

He also punched and shot just like the leader

[@eljefe308]

Everyone staying in character combined with the improv is actually pretty impressive. The way the guy screamed medic as he was picking him up brought a single tear to my eye dagsnabbit

[@squeebbb]

well, that's the point. It's a roleplay server.

[@eljefe308]

@@squeebbb no way? Thanks for the insight!

[@Earthcouldnotanswer]

@@ArashiKageTaro haha yeah right

[@CruizINcognito]

​@@squeebbbyou're a smart fella aren't ya

[@notteddanson7226]

Check out Neebs Gaming if you like immersive gameplay.

[@deathfiction6122]

That potential moment of intimacy between Darnel and Miss Cunningham ruined by the tesla coil killed me. 😂😂

[@distinguishedallureproduct879]

If I was the delivery driver I'd be watching through the window this like a movie

[@looney60]

Shiiiit in a basket 😂😂

[@thetillerwiller4696]

Frrr. I was rooting for these two since that chat they had

[@RealSurfDog]

24:50 Was so ruthless 😭 actually seemed like it was out of a movie or something. “no he ain’t had enough yet”

[@techtikbruh]

That timing and delivery deserve an oscar 😅

[@insatiabletoad]

i truly want to partake in an event like this

[@ColonelRogers]

I love how it was all in response to a misclick lmao

[@S0phisticatedZ0mbie]

My boy cry-rolled into a bed of roses

[@dolphin5177]

Reminds me of season 5 rick from the walking dead

[@Superbl0bby]

"if you ever think of changing the world, don't ask for permission." - Some guy in an RDR2 roleplay server That is an amazing quote

[@Ozone946]

From Viktor, Arcane season 1, actually.

[@RomanTorchwickRWBY]

@@Ozone946still sick as fuck

[@f_youtubecensorshipf_nazis]

It's an arrogant and short sited quote that ignores structural aspects of society. but sure.

[@mushrooms5757]

@@f_youtubecensorshipf_nazis It's a cool quote that fits well the timeframe, given it's the very turn of 20th century. Don't act a sour wiseass for no reason.

[@LuckyKlvrSyx]

​@@f_youtubecensorshipf_nazisit's a great quote, actually

[@swilllow]

8:49 that little "i love you" while running away had me dying of laughter lmao

[@thetwistedsamurai]

im so glad someone mentioned this cause i DIED

[@hereforthecomments9676]

So funny!😂😂

[@TheCiabattacado]

Him yelling for MrDewwit then realizing it was his name had me dying! I wonder if that was intentional or if he was just embodying the character that much it took over a bit, either way, loving this!

[@alondra2317]

Literally in tears reading this and watching it at the same time. 😭😭

[@TheSlugJones]

Got me, too. I got to giggling and tearing up laughing. 😂

[@sendbigironpics2090]

“No he ain’t had enough yet” followed by that execution was a scene straight from a movie

[@Ausvwidabix2blorange]

IT WAS SO CINEMATIC

[@matts7125]

I instantly thought of shane from the walking dead in that one scene on the farm

[@usedforks]

That legitimately upset me

[@ishmaelhwasim]

IT WAS SO GOOD BRO I LOVE THIS VIDEO SM

[@600_pac8]

@@matts7125sameeeee

[@blockingthesunmusic]

Lmaoooo when they accuse the sheriff of being a werewolf and they all draw their guns 😂

[@PD_Swag]

Hands down some of the best role play I’ve ever witnessed. You, the sheriff and the medicine lady sounded like elite-level voice actors. It felt like a movie at times and to think it was all improv is just incredible 🤯

[@erosion7618]

Those 3 should've been legit voice actors for rdr2

[@oh_knee7173]

i need a god damn doctor!!!!!!!!!!!!@@erosion7618

[@T0e-Man]

Honestly VA takes practice.

[@XenuLordofTheSky]

@@erosion7618 Well this came out after rdr2. Soooo.

[@ogknitely]

@@XenuLordofTheSkyyea no shit bud, great observation

[@MsJackieJack]

the way sheriff was absolutely triggered after being called a werewolf had me rolling

[@MsJackieJack]

Lmao Dewitts execution of the cactus brother, fall in flowerbed, with the sheriff calling and looking for him in the background 😂😂😂

[@4000Wiggins]

How are there so many talented voice actors in this game?

[@IIIIIIIllIIIl]

It’s not complicated to talk like a hick lol

[@sYndROCK]

most are actors...

[@RandyOrlok]

Voice acting isnt a talent, they are just born with good voice

[@seriousnesstv7902]

@@RandyOrlokthat is what a talent is

[@RandyOrlok]

@@seriousnesstv7902 so being good looking is also talent? Or being tall? No, it's "good parameters ", not talent

[@Menos510]

Lol "when you shoot a man in the head, his soul goes into your nipples" what a line

[@cheemsg.i.7130]

Lol

[@emanuel81111]

cowboys back then surely knew their thing

[@cheemsg.i.7130]

12:28 Insane dedication into her character

[@bears2life366]

Bro she should be a voice actor if she ain’t already

[@jaydub2546]

Yeah she's good

[@viderevero1338]

She was actually incredible. I was shocked that entire interaction, because she sounded straight from the actual game. Might've been the best voice actor in the group.

[@typical947]

Truly insane voice acting, easily the best ive heard in a non official capacity

[@okitasan]

I believe the name of the player is DisbeArex

[@chrish1986]

"You ever think about changin' the world there, don't ask for permission. Do what ya gotta do." -Mean Gene

[@ASSOL3]

Such great one liners, these people are great!

[@tauschen507]

I think thats a line from a something else

[@usedforks]

I thought that was a pretty odd quote from someone in a position of authority. Then again, considering his turn, it sort of made sense in retrospect. Would have been amazing if Darnold had brought that back up to protest the execution!

[@isick357]

“I’m a man who doesn’t think too much. Thinking is hesitation and hesitation is defeat my friend. The moment I stop to think is the moment I die” -Mean Gene

[@xdlilsquirt]

Whats the timestamp

[@anyabailey3861]

The woman reversing the wagon is insane she needs hiring for future rdr games

[@yeahokbuddy2510]

She sounds beautiful

[@Nantosuelta]

@@yeahokbuddy2510 she sounds like a voice actor

[@TheBTeamOfficial]

The Murder of the Cactus Brothers was absolutely Grammy worthy. Stand out performance was Dewitt's immediate crying run/trip away, along with the ensuing "I DOHNT huWANNA LEEV NOI MORR" 👌😂That made my life more complete than I ever knew possible. Gonna have to sub for more of these shenanigans!

[@cursivejay]

The building storm was insanely cinematic

[@TheArtistFormerlyKnownAsCunt]

Acting so good it was worthy of a music award? 😂

[@usedforks]

@@cursivejayI think Thomas and the guy playing the sheriff definitely took it as a cue. Who knows how it might have played out if the weather were different!

[@ryanlupton3157]

This is gonna sound strange but when I heard "I don't wanna live no more" I was reading your comment. Specifically that quote. Strange.

[@jacobweathers5232]

The scene at 39:46 had me crying laughing. She's now going to have to try to explain what she just heard.

[@SmokeEater509]

Should’ve done the O Brother Where Art Thou “DO NOT. SEEK. THE TREASUUUUURE”.

[@PB_TheOldGuard]

What exactly did he say at the end? Thats a real eerie thing

[@S0phisticatedZ0mbie]

A perfect end

[@acanadian80]

That’s such an anticlimactic way to die, but realistic because most people don’t have a heroic death.

[@usedforks]

6:05 This type of storytelling is literally the future. The stakes are so high because you feel like you’re actually there -- there are no predictable beats because the story is being told in “real time.” And the suspense is REAL because literally anything could happen. Nobody is safe! And the best part is it’s almost infinitely rewatchable! You can watch the same content from each character’s perspective and get a brand new story every time!

[@chibilutionaudios]

wait until you find out about D&D

[@TheBlackbaron95]

Western d&d sounds awesome ​@@chibilutionaudios

[@chibilutionaudios]

@@TheBlackbaron95 yussssss

[@Urglerbob]

Some of the best VO I’ve heard, everyone was super spot on, so talented, especially Jean the doctor!

[@mchristian2142]

If I wasn't watching the video, you could've convinced me that was an actual NPC doctor with the level of voice acting.

[@drabc1235]

What is her accent called?

[@premedreem3634]

@@mchristian2142 yeah shes genuinely talented

[@ncthcly]

right if she had a channel i’d subscribe in a heartbeat

[@BobaFett895]

Phenomenal voice acting, seriously blew me out of the water

[@jrockn77]

The line about milkshakes had me laughing so hard I woke up my son. Glad I have the rest of this expedition to entertain me while he goes back to sleep.

[@osoloso4863]

But it’s a little wetter 😂

[@BobGreasen]

The thing is, milkshakes were entirely different back then, so it had nothing to do with ice cream. A milkshake in that era was a frothy, alcoholic beverage made with eggs, whisky, or other spirits, along with milk, sugar, and flavourings.

[@didlymosy]

I like the full out screaming at 16:02 a lot of time rpers just be like "ahhhh" "ah" butyou could hear some PAIN in his scream

[@chineseobama6043]

Goddamn the execution scene was so brilliant, the storm rolling over really brought in even more tension and the moment the thunders final echoes fade out the sheriff executed the cactus brother with a line so cold "he ain't had enough."

[@SalomeLuna69]

Running away crying after he shot that feller was hilarious and then the trip and fall😂

[@seantron5687]

This had me in tears when they were reading the journal after his death. Tremendous

[@plp50000009]

13:06 “shahiiit in a basket!” That’s method acting ladies and gents and I love it.

[@LcLeaning210]

I feel as if dewitt became more cold hearted as he goes along the road of the law it would make a crazy character development

[@Bludlungg]

What makes this so much better is they can actually voice act and think on the spot

[@sundewdoesntcare]

Improv broski. It’s the best

[@Tr3duty3]

You earned my like when you said “if you ever get a chance to have a milk shake you outta try it, it’s ice cream but a little wetter”

[@bengulliver5040]

Whats wild is I have more fun watching this than most of 1mil+ budget productions on Netflix. Keep em' coming T bone!

[@squirrelmaster8160]

Facts

[@Meadjuice]

My guy i was thinking the same shit recently. Twitch content, youtube content, its all i watch. New movies and shows dont hold a candle to online content. Keep enjoying my friend x

[@OddSynergy]

Seriously I felt that

[@mrdude88]

This is more fun than anything that was in theater in the last 8 months.

[@flamee23312]

This isn’t produced with the goal of making money. There’s no investors to answer to, no money to worry about. It’s just people gathering together to escape their lives temporarily and make their own story. It’s just pure fun and love between all of the members.

[@choesnow]

bro i cant breathe at "when u steal somebody's soul by shooting them in the head, their soul goes into your nipples" this is incredible

[@jameyspielt]

this is art.... I tried to play many games like this RPG style... never had the mates to do it right... maximum respect to the whole crew!!! and especially the 2-3 women who are doing a great voice acting job.... just like @thomas Middleditch say at about @20:30 ... awesome impro! .... and Cats are awesome!

[@squeebbb]

the problem with most people in RP servers is they aren't there to roleplay. they just want to grind money, buy guns sell drugs and swing their dicks. that's not RP.

[@natelaw2731]

same here. looking for a crew myself

[@marleyfrost215]

What platform are you guys on? PlayStation here and I’m dying to try this!

[@BeesWithKnees]

@@marleyfrost215 I'd love to do this but I'm on PC :( wish more people would do it

[@keane2160]

@@BeesWithKnees how do you do this?

[@mixedraisins]

27:51 that funeral speech had me in stitches. "All I can say is *SPITS* F you Cactus brothers" Hilarious, thank you

[@jayteepodcast]

This is what a wish multi-player would be like

[@distinguishedallureproduct879]

Facts we try this in RDRO and everyone would be dead by a Naked hillbilly with dynamite before we even gotten on the road 🙄😭

[@Mykeynikey22331]

It's the little things in these RP videos that get me laughing. Saying "I love you" before running away has me dyin 😂😂😂

[@jones2001]

When she burned darnold’s body and T started spouting some random ritual shit and she said «What the fekk» i was laughing so much

[@linkan907]

I rarely comment on youtube videos, But i just have to say that this is a masterpiece. I want 10 seasons. RIP, Darnold Dewitt

[@anonymous_00110]

Darnold DeWitt is the epitome of "It ain't much but its honest work". Great video as always I had a blast watching this!

[@ReedyD1953]

I am honestly so impressed that someone with the fame of Middleditch chooses to spend his time playing this game. It is such a great experience and I think it meshes really well with his personality.

[@r_yo]

i thought the same thing, i didnt even realize at first since this video randomly popped up, but then i actually looked a little harder and was so surprised LOL

[@Shamino1]

I have no idea who Middleditch is and I came here because I like Red Dead 2, which is probably one of the most popular single player games of all time. Who the hell is Middleditch?

[@roivasethar8079]

Sillicon Valley is a great show he is in@@Shamino1

[@swampyproductions6755]

@@Shamino1he’s in a fair amount of popular modern media, movies, tv shows etc. funny feller and seems like a genuine one too

[@huntermcneil2201]

@@Shamino1 I know Thomas Middleditch from College Humor as a guest on Jake and Amir. Loved his work in Solar Opposites. Much like OP, I am absolutely surprised to see him streaming this masterpiece. Surprised in a good way. This is one my favorite games, so I love seeing him play it.

[@691ratatataa3]

26:45 was just PERFECT🤣the fall and jus laying there crying😂the Game itself was on these ppls side

[@frogg5949]

8:46 the 'I love you' had me cackling

[@GumNeckEnduro]

Tragic loss of a good man. I was really looking forward to more of this. Can You please be more careful, Middleditch! This was heart-wrenching. Yet, strangely, my nipples are diamonds.

[@IIIIIIIllIIIl]

Tf

[@TheRealSandorClegane]

Wtf?

[@MistOrFog]

real

[@jakas2524]

did u not watch the video@@IIIIIIIllIIIl

[@Samagachi]

He just like me fr

[@skittlemctitty]

24:49 is so damn perfect lol

[@MrEL91N]

My jaw literally dropped

[@bubu3625]

Need another RP with Mean Gene. You two are pure gold together, perfect dynamic

[@usedforks]

Ms. Cunningham is really really good. She sounds like a professional voice actor!

[@busterscruggs8834]

He saw the caracter and already has a voice that fits perfect. Thats just genius

[@RukiaHilde]

My god, when Dewitt ran away crying and then fell down 😹😹😹 good stuff

[@teraj98]

“It’s ice cream, but a little bit wetter” that got me 😂😂

[@RomanTorchwickRWBY]

This is the fastest 40 minutes that have passed in my life. The story was purely just a prompt, and then improv, and it was fucking fantastic, in the pacing especially. The ability and character of all the players is impeccable, and only done better by the amazing voice acting. The poetic undertones that other commenters have pointed out are also absolutely amazing, such as how his guilt over killing the Cactus brother being symbolised through the red petalled flowers he lays in, and how a good man like Darnold could never survive on the Oregon Trail, as helping a horse was the eventual cause of his death. I didn’t think something could make me connected to a character so fast, but it worked, and it worked well. I’d love to participate in one of these such events, even if it could only be a fraction of the character complexity and improv skills.

[@bnacronama_na947]

I have never been more invested in RP content than I was when watching this video. I hope I get to see more of this and would love to see this character return for the next Oregon Trail event.

[@isick357]

These people are really building something great. Everyone staying in character reminds me of a civil war re-enactment I saw as a kid. Also renaissance fairs. It’s like re-enactments but more accessible, and probably more accurate and immersive. Except whenever a cart goes flying into oblivion lmao.

[@mattjarrett7274]

Why was this so good? 😂 that's some next level improv from everyone involved.

[@IanPhilmore]

Actors doing improv through online roleplaying games is genius.

[@PharaohG8D]

The sheriff is so inspiring 😂😂😂

[@frostinflakes_god]

This was to emotional for no reason, like better acting that most shows/movies, emotional experiences and tragic passing. Love how everyone played their role

[@silberiax6692]

This is peak roleplay. I would love to travel along these guys.

[@erickmuller]

This is my favorite character you’ve done. So funny

[@virus_v73]

The way Dewit fell @26:48 had me DYING

[@shaboodle]

Fuck. I felt that loss deep in my hardened areolas.

[@Astreious]

Brother what

[@ReyFelipe00]

@@AstreiousNeed to finish the vid for context tbf

[@Eburon]

I'm not familiar with online role-playing, but this is incredible. Some real voice talent here

[@rorygibson3124]

This was phenomenal even though it was so short. Does anyone know if there are any more videos captured by the other players?? Would love to see how the rest of this trip shook out.

[@holly2786]

i think the best pov to watch all the way to the end of the trail would be ziggy who played the character of mumbles. i dont know if it has been put on his vod channel yet though

[@johno6787]

My dude the video is 40 minutes long

[@EP2005]

More of this! it was surprisingly engaging and you seem a perfect fit for this. Your voices for “particular” characters are great. Subscribed for more of this!

[@GigHarlemProductions]

Damn the voice work from everyone is so good.

[@yellow_yacht]

mr. dewitt running off into the night sobbing while the sheriff calls after him after committing an execution was unironically peak cinema

[@frontiersman1863]

And how he just fell

[@torut65]

In passing “some people are talking about eating all the ladies but I rather eat all the big fellers.” 😂😂

[@jordanlong5554]

"What are your dreams and aspirations" "I like cats" she's going places

[@justdeuced7441]

“It’s ice cream but a little bit wetter” had me dying 😂😂

[@Alcamest100]

Some of these people sound so damn good, their mic quality has them sound like theyre part of the game as well. As a guy who does many voices this video makes me happy and i havent even finished it yet!

[@dereklong2072]

Damn dude Darnell's death hit me kind of hard. He was just a kind soul. He didn't deserve to go out like that. Then seeing the reaction of everyone to him dying was great. This whole experience felt like a movie.

[@mark-sg6wo]

I cried when you sang tooralooraloora, my mom used to sing me to bed with that song. It just hit real deep watching Mr. Dewitt pass singing that because I saw myself.

[@emanuel81111]

It felt like a real rdr2 story , like a dlc of some sort, but they are all players, HOLY SHIT! This is amazing

[@Jax303]

16:20 “he’s turning into a werewolf!” 🤣🤣🤣

[@laya8880]

Why is no one talking about how the sheriff is dressed like Woody from Toy Story😭

[@yellowmayo1262]

Woody is cold 😂

[@giantenemycrab420]

When bro playing the banjo stood up and took off from the wagon and went and beat the shit out of the dear 😂

[@brandonchapman6363]

Bro, when he had to kill the 2nd Cactus brother 👏👏👏 Now that was cinema 😂❤

[@ShotByZy]

Bro … RDR 2 is literally THE BEST game ever made, so sad they don’t show it more love

[@WBM219]

This was like a whole movie, the characters, the conflict, the rollercoaster of emotions, absolutely beautiful. John Wayne and Clint Eastwood would be proud.

[@Nantosuelta]

when you shakily sang tura lura lura in the Dewitt voice. Absolutely hilarious

[@neverend3r]

I love RDR2. but this role play stuff just takes it to such a top tier level. I wish I had the guts to try this.

[@caramelchaos]

Just do it! My group was very nervous at first but everyone was very helpful and welcoming

[@GhostInPajamas]

@@caramelchaoshow do you get into it? This seems like a special kind of server

[@caramelchaos]

@@GhostInPajamas the server he's on is a white-listed server, so there's an application. This is preferable, and helps create a great RP experience. There are some servers that are allow-listed that are not bad either. You just have to have RDR2 and RedM. Start checking out the servers (some will be better than others) and dip your toes in!

[@bullettebug]

@@caramelchaosi’d also like to know what the other person asked! did u have to have lots of experience?

[@caramelchaos]

@@bullettebug you do not have to have a lot of experience! Most players are very helpful to greenhorns (newbies). I recommend a white-list or at least allow list. Read the rules, follow them, and have fun! More serious servers may have more strict admission criteria but there's not a bunch of those. Bandera County is a white list county I would recommend 👌🏾

[@CuttySobz]

The herbalist lady sounds like a pro voice over person lol

[@P1PWR]

That execution is giving the Walking Dead a run for it’s money

[@huntermcneil2201]

I loved watching Thomas Middleditch appear as guest on Jake and Amir during the CollegeHumor era. Now I love seeing him here playing one of the greatest games of all time.

[@doriansdemonn]

I’ve never been interested in RP videos until I saw this. This was so fun. So many talented people.

[@austin10310]

This is some of the best Rdr2 content on KZbin. The way you all stayed in character was amazing! I absolutely love the community of this game. Everyone is so peaceful and just wants to have a good time

[@Aspect_20770]

This right here feels like next level roleplaying seriously impressive

[@Cjoudan]

Usually I think this stuff is silly, but this was great! Yall been an animated series or something.

[@dhdvecsgcghvdtfsr526]

It’s only silly if people take it too seriously

[@Hewarya]

"I believe one of the Cactus brother's just stabbed me" 😂🤣

[@CarnaxdudeYT]

10:04 - "THAT IS A FEEYUSH" Loved the reaction hahaha the immersion is incredible

[@SmokeEater509]

This was one of the most entertaining video game videos I’ve ever watched. Merging RD2 and a classic like Oregon Trail, with players who stayed in character throughout was next level.

[@filmbotreviews]

That was probably the most entertaining 40 minutes I've had in a while. Damn, that was such a good journey.

[@zack7355]

I loved this so much. I was shocked when Dewitt got blasted with no warning .

[@coffinmyface4237]

Dewitt and the russian lady have some pretty good on screen chemistry, their little conversation was very fun to watch

[@ImCalvinr93]

The voice acting from Jean Cunningham is breathtaking.

[@HappyHauser]

This is the Dewitt’s brother piece of puzzle I’ve been missing all this time. THANK YOU

[@mongooseodon7608]

I loved this so much, everyone’s voice acting was fantastic! I especially loved the doctor and sheriffs voice, so awesome!

[@whitecocoa42]

something about this was real special. it seemed like the acting only got better as time went on. heartbreaking ending.

[@fknpanda7280]

pleease do more stuff like this, this was such a great video. Darnold was a great man, and his life was cut too short. in his honor i will go try a milkshake