The Runaway Guys Fortune Street / Funny

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Yoshi's Island

The first lines of the whole LP.
Emile: "Today, we are going to the most dangerous world that we have ever been to. The dangerous, dangerous world... of FINANCE AND ACCOUNTING!!!"
Jon: "...And then everyone turned off the video."
The voice Jon does for Waluigi. Emile points out that it sounds like a bad Mexican accent.
Jon: "Waluigi's now determined to be the worst Mexican accent it can be."
Emile: "You might as well go 'Arriba, arriba! Ándale, ándale!' if you want to make it worse."
Jon: "Waluigi number one! Ándale, ándale!"
- After Jon accidentally invests 999 gold into an arbitrary shop (which everyone, himself included, calls "a mistake"), Emile uses one of his later turns to look at what the shop Jon invested in actually was. It turns out it's actually a bridal boutique. Mexican Waluigi's lines only get more hilarious after that.
  Jon: "Okay, no, that [1109G] price makes a lot of sense, actually."
- It gets even more hilarious when Emile tries to argue that Waluigi is aiming for the gaming community because only they would trust him. Jon's reaction is priceless.
  Jon: "Who in their right mind would trust WALUIGI?!" [Mexican Waluigi voice] "I look trustworthy, look at my mustache!"
- Emile, having kept generally quiet about the voice, randomly cracking up as Tim decides which district to buy stock in.
  Jon: [Mexican Waluigi voice] "District A has very good stock prices^note."
  Emile: [Beat, bursts out laughing] "What are you doing!?"
  Jon: [unfazed by Emile's comment] "District A likes your money."
  Emile: "You sound more, like, Mexican."
  [both Jon and Emile laugh]
  Emile: [imitating Jon's voice] "These are really good stock prices, arriba arriba!"
- After Jon buys a certain building, he sees Waluigi flexing and again does the Mexican Waluigi voice, only much more deeper than usual, prompting him to say "My Waluigi voice's turning into Wario, apparently."
Emile jumping up and down on the bed after escaping a risky island unharmed.
Tim being allergic to bullshit.
Emile: "It's a bookshop, that would have been bankrupt in the year 2012."
Jon: "Well, it's a Yoshi's Island bookshop. Yoshis are just learning how to read."
Emile: "Well, Yoshi's Story was in a storybook."
Tim: [fake sneeze] "Sorry, I'm allergic to bullshit."
Jon: "Ha! Haha, that was pretty good, Tim."
After Emile refers to a particular district Jon has a lot of money in the Grand Line, he and Jon get into a bit of discussion over the anime, before they both have fun mocking the 4Kids intro.

The Observatory

In the second playing with Reese, Tim willingly lands on a space that closes all of his shops.
Emile: "Why'd you close for the day? You could've gone to the arcade!"
Tim: "Yeah, I could've."
Jon: "Or you could've gotten a suit."
Tim: "I'm just trying to go easy on you."
Emile: "OOOOOOOOOOOOOOOOOOOOOOOOOH!!!"
Jon: "What? WHAT?!"
Emile: "Damn, boy! Tim's got an ego now that he's won!"
Tim: "You can just call me Egoraptor."
Emile gets a card that causes Lakitu to appear, but nobody knows what he does^note, so Jon turns the chat on so Lakitu will tell them. Every time he gets a turn, though, somebody skips the explanation, to Jon's growing frustration.
Jon explains the game mechanics to Reese, who has never played the game before. Towards the end of part 1, Emile calls him out on having gone into "teacher mode" as Jon calls it.
Reese: "I'm gonna get an A!"
In part 2 they have an argument about how Reese cleaned Emile's kitchen for him, Jon unpacked his groceries, while Tim...played video games.
Reese's "How many Mexicans does it take to change a lightbulb? Juan!" pun is so bad that Emile high-fives her.
Tim's rendition of The Lion Sleeps Tonight.
Jon's "Mexican Waluigi" voice starts to wander into Tommy Wiseau territory, as Emile notes.
Jon worries that people will call him gender biased for being nicer to Reese than the others. This segues into Emile saying that the only way Jon will ever be nice to him is if he has a sex-change operation.
Emile buys a pharmacy in District E to prevent Jon from having a monopoly, prompting this exchange:
Jon: "Is that a drugstore?"
Reese: "Yeah."
Jon: [Mexican Waluigi voice] "How dare you stop me from running drugstore! Do you know how much medication I need a day? I need 30 packs of Xanax to stay so angry!"
When Reese goes back to the bank with one move left, she lands in a direction that forces her to land on one of Jon's adjacent properties.
Jon: [Mexican Waluigi voice] "Which place would you like to give me money from?"
Reese: "... My ass."
Jon: [still in the voice] "I always did wonder where the pockets were on that thing^note(Daisy's dress)."
Emile: "..." [cracks up laughing] "What!?"
Jon: "Hey-ooooo!"
- And after the above, Tim starts going on about Daisy having a reverse camel toe before Emile says she's a reverse kangaroo. (This part of the conversation is most likely talking about the high heels Daisy wears with the dress)
In part 3, when Emile points out that Waluigi hasn't actually done anything that evil in the Mario canon, Reese claims he's evil 'because he has no ass'.
The Running Gag about Jon's purple sector of the board being 'the ghetto' because of its low rent prices, and then Emile points out the Unfortunate Implications of this being coupled to Jon's "Mexican Waluigi" voice.
- Also leads to this moment of Buffy Speak when the stock prices go down in Jon's sector. "The ghetto is even ghetto-ier!" (And later "stop ghettoing up my ghetto!")
After seeing Waluigi stand on a shop space in a pose that makes him look like he's sitting on a toilet, they decide that the toy store he owns sells toys made out of his poop.
Emile and Reese agree to do impressions of each other. After Emile does a bad impression of Reese, she responds by imitating his frustrated "AAARGH!", and then Tim joins in as well.
Jon (as Mexican Waluigi) insults Mitt Romney, then Emile reminds us that this video was recorded before the election and Jon could be insulting the current president by the time it goes up. This leads to a discussion of Jon being arrested the next time he tries to go to the USA and 'having an interesting story to tell in prison', then the suggestion that a future project would be "Let's Play Prison Visitation".
The Guys not noticing Jon's gone when he just gets up to go and get a drink towards the end of the video, and him being outraged about this when he comes back.
The end of Part 4 has an epic moment of Tempting Fate. Jon invests a large sum in improving a store which Tim is 1 away from, then Tim gets a card which increases the prices on every property by 30% for one turn. Emile says heavily "If he rolls a one..." He does.
- And then Emile gets the unlucky 13 card, reducing all his prices by 13%.
In part 5, Jon gets enough net worth to win while he's already on the bank... only for the game to force him to go away from it and come back again.
- The video is promptly fast-forwarded past the next few turns and eventually returns to normal only to find the group singing/beatboxing some Montell Jordan.
Waluigi's speech as President Evil when he wins.
The post-result screen segment:
Reese: "Thank you for having me! I'll go back to, uh, cleaning the kitchen now."
Tim: "Yup."
Jon: "Yeah, çuz I think it needs it."
Reese: [laughs] "It does!"
Emile: "That's what you're here for."
Reese: [laughs again] "I knew it!"
Emile: "No, that-"
Jon: "He finally admitted it."
Emile: "That... and doing the laundry."
Reese: "Okay. Oh well..." [Beat] "Small price to pay."
Jon: "I'm sorry our fearless leader is sexist."
Reese: [laughs] "Hey, he's the mexican! How come I have to clean the house?"
Jon: [inhales] "Nevermind you're racist."

Mario Stadium

In the Mario Stadium playthrough with JoshJepson, Josh's confusion when he rolls a 7 and Jon referring to it as 'rolling an H'.
After Emile comments that this is the second time they're playing through with someone unfamiliar with the game and having to teach them as they go along:
Emile: "We are good teachers. We should be running the education system!"
Jon: "NO WE SHOULDN'T. Speaking as the son of a teacher..."
Emile: "You son of a teacher!"
In part 2, Waluigi's got a coffee shop. Emile then jokes that it's called Wabucks and that if Waluigi printed money it would also be Wa bucks. They then joke about what Waluigi would look like in the different bills.
Josh referring to "Knuckles the Enchilada".
They joke that (due to him cutting abruptly from the upset paying-out animation to being happy again) Yoshi is bipolar. Jon's impression of him as such rapidly degenerates into Niko Bellic. This then leads to them creating a Crack Fic in which Yoshi replaces Roman in Grand Theft Auto IV, with Jon voicing Niko and Emile voicing Yoshi.
In part 3, Josh: "I wish someone would pay me to be stupid..."
In part 4, Emile and Jon discuss Jon's habit of rolling low numbers on board games, ending with Emile saying "Jon always rolls ones, it's his thing" — upon which Jon immediately rolls a 1.
In part 5, the other Guys don't notice Emile building a big lead through stock prices when he puts cash into a district, as Jon and Tim are too busy discussing whether the Elton John or William Shatner version of Rocketman is better.
Josh forgetting to press 2 to move the dialogue boxes along and Emile having to constantly remind him.
Jon and Josh begin to sing in perfect harmony: "Iiii'm dreaming of a Jesus Christmas, just like every other Christmas there iiis..."
Tim: "With a blood-yyy cro-ossss... and... ...Sorry." [Everyone else is stunned]

Slimenia

Emile imitates "Tim's Waluigi voice". Jon catches the slip-up immediately, and Emile prompts Tim to impersonate Waluigi. The guys liken it to Donald Duck as a drunkard.
In Part 3, Emile lands on three of Jon's spaces in a row, and complains about this (ignoring how Jon keeps pointing out how small the payouts actually are). His very next roll lands him on the space Jake built up.
After gaining a healthy lead, Jake screws himself over by accidentally buying one of Tim's properties for five times its value.
How the game ends: Jon lands on a suit and gets a card that lets him warp to any other space. He immediately warps to the other remaining suit that he needs, where he then gets another card that lets him warp to the bank and instantly win the game. The Guys' stunned reactions just sell it.
The Running Gag of referring to Jake (and/or his player character Stella) as "a seven-year-old drag queen".
When Emile briefly leaves to use the bathroom and Jon fills time by pondering which stocks to buy, Tim slips into a Wildlife Commentary Spoof voice describing the whole thing.

Delfino Plaza

The irony (pointed out by an annotation) that Emile starts the game by talking about how Jon is winning everything lately. The board was recorded before Jon's terrible luck throughout Mario Party 3.
Emile's surprisingly blunt Take That! to the Game Grumps after Jon brings them up.
Emile makes a mention of Tim's Wiimote battery being low, saying it would pause the game... Then rolling a 3, landing on Tim's biggest property, with a cry of:
Emile: "Watch it pause the game until he reconnEEEEEEEEEECTS!"
[cue synchonized slow clap from Jon and Jake]
Jon's story about how he almost didn't make it through American customs for Let's Playing.
After winning the Slurpodrome event, Emile made a reference to "The Super Speedy Cider Squeezy 6000".
Jake jokes that he has Psychic Powers that let him predict that the next person will roll a 4. Emile says how funny it would be if that actually happens. Guess what the next person (Tim) rolls.
A similar Tempting Fate moment when Emile suggests Tim might get a row of 7s (the highest scoring combination) on Round the Blocks, which Emile has never seen ...and he does.
Three players get total domination (i.e. monopoly) of districts in one part.
Tim is 1 away from Jon's most expensive shop and Emile is 1 away from Tim's. Tim rolls a 1 and the payout demolishes most of his massive lead...then Emile rolls a 1 and Tim gets almost exactly the same amount back again, restoring his lead. All in one turn.
Jake lands on the cannon and his only options to shoot to, the other three players, are all in 'the Circle of Death' as Emile calls it, made up of Jon and Tim's monopolised districts.

Mt. Magmageddon

Street of Fortune with Proton Sajak and Tim His White.
Masae introducing herself.
Masae: [in a deep voice] "I am MasaeAnela, clearly the manliest one here!"
Emile: "The sad thing is, that's probably true."
"Also, more bars in more places!"
Everything about Carver is systematically designed to be hilarious. Including the fact that he's being played by MasaeAnela.
- He's about twice as tall as any other character in the game, including Waluigi.
- His Idle Animation consists of him constantly flexing...
- ...But when he walks, he prances.
- His high-speed prance when the Guys speed up the game is good, too.
- Everyone cemented it with their Arnold Schwarzenegger impressions.
- Jon started taking it up to eleven in episode 2 by combining his Waluigi and Arnold voices.
Part 3 has even more of Jon's Waluigi voice slipping into other accents and voices.
Jon: [sounding like Morgan Freeman] "Waluigi number one."
Jon ranting as Carver only for him to start sounding like Jorgen Von Strangle.
- "SCRAMBLE THE FAIRIES!!!"
- Part 4 has Emile's microphone being taken over by an elephant and Waluigi's voice now becoming that of Pee Wee Herman.
As different players grow to dominate different parts of the board (which can split up into "islands") this leads them to dub the different regions "Yoshi's Island", "Waluigi Island", and "Muscle Island" (split between Carver and Donkey Kong).
- Masae making the same mistake Jake made and accidentally buying out a property.
  - At least it wasn't the reason she lost the board. Though that's its own funny moment.
Jon spontaneously pulling off an incredibly deep voice, and then being unsure if he could replicate it or not.
Jon: [in the deep voice] "Why didn't you play the minigame?"
[Beat]
Jon: [in the deep voice] "Why didn't you play the minigame?"
[Beat]
Jon: [in the deep voice] "You're not answering the question."
Jon: [in his normal voice] "I don't even think I can do it again now if I want to do it on purpose, that's the worst part. It was just one of those 'how'd I do it? I dunno'."
Jon: [in the deep voice] "I'm going to try doing it again. Okay never mind I can keep doing it."
Masae: "You just test it out?"
Jon: [in the deep voice] "That was just a test."
- He then forgets how to do it in the next video.
Jon says Masae had better not roll a 4, Masae proceeds to roll a 4, Emile screams in reaction, Masae screams along with him — and then an annoyed Jon points out that he meant she shouldn't roll a 4 from his perspective because that's the only roll that wouldn't have her land on one of Jon's properties.
The ending of the board.

Robbin Hood Ruins

Slightly meta, but the fact that Part 2 was uploaded before Part 1 by one minute was somewhat funny.
Their rendition of the opening song from Robin Hood (1973).
In part 2, Jon buys an expensive property early game. They check out what was the property, which was a fossil shop.
Jon: "You want to buy some dinosaurs?!"
Tim: "You want to buy the Helix Fossil?!"
From Part 1, where Reese introduces herself:
Reese: "Hi, I'm Daisy!"
Jon: "We got the Daisy, everyone!"
Reese: "I heard Chuggaaconroy loves me a lot, so I came out here—"
[Jon starts laughing]
Reese is playing as Daisy, the Emile x Daisy shipping jokes run full throttle and, many times, no one even has to say anything as Emile says it all.
Every second between 3:25 and 4:30 in part five. Emile talks about figuring out why it's called "shipping".
Also in part 5, Emile getting confused about Reese giggling over innuendos because he can't figure out why they would be innuendos.
- Continues in Part 6, to the point where he doesn't seem to understand the sexual context of "going down".
Reese buys a lot of property in a poor district, which leads to a Running Gag of referring to the district as "the hood".
- Once Reese buys every property in that district, Emile cries out in sheer despair, "She monopolized the hood!"
The description of Episode 6 is "The gas we pass." Needless to say, one commenter decided to have fun with this.
The gas we pass,
Comes from the ass,
Suffocating you with the atomic mass.
Some may consider it crass,
But some may say it has class.
Strong enough to shatter glass,
The air could play an instrument of brass.
Now, Tim don't wanna hear none of yo' sass.
Tim's epic fart in Episode 7, which not only completely derails the commentary, but leads to some innuendos so bad that even Emile gets them.
Jon and Emile getting desperate and literally taking their shops to max value. Emile loses by not having enough to win.
As they finish the board, Jon wins yet again, Emile warns him of how much longer Starship Mario is than the board they just played. The video reaches the outro and the ending theme, when you hear Emile shout how long they spent on the board:
Emile: "TWO HOURS AND THIRTY-SEVEN MINUTES!"

Mario Circuit

As noted in the comments, the first episode ends up unintentionally being 'the educational episode' due to Tim mentioning the atomic number of technetium in his intro and Jon talking about the etymology of the word 'monopoly'.
- Tim and Jon have an exchange of bad puns which passes completely unnoticed by Emile...
  Jon: "Getting bought to find a district to actually buy..."
  Tim: "Say good-bye to some more stock."
  Jon: "Yup. Un-fortune-ately."
  Tim: "Hee hee hee hee!"
Jon asks if Masae carries a taser. She says she's considered it. Emile then jokes that she carries a knife. Which Masae confirms. The guys are deeply concerned by this revelation.
Masae: I'm not going to use it on anyone, in case you were wondering...
Emile: Except me, when I make puns.
Masae: Nooooo, not even then...
Jon: I feel like if that was the case, she would have already used it, and you would have bled out a long time ago.
Masae lands on a dice square to avoid paying Emile some money. On her second roll, she lands on one of Jon's that required a bigger payout. Cue Skyward Scream.
On two separate occasions, Masae gets the exact dice roll she needs by wishing really hard before she rolls.
Jon is apparently psychic:
[Jon gets a venture card]
Emile: "More ventures..."
Jon: "More adventures in picking terrible cards!"
[It's revealed that it is indeed a terrible card, Jon immediately cracks up]^note
Masae: "Are you psychic?"
Tim: "Whoa."
Emile: "Dude!"
Jon: "Sometimes I wonder."
Emile: "Maybe the glasses make him that way."
Tim's lip squeak in Part 6.
Jon receives a venture card that allows him to buy any unowned shop on the board...except that there aren't any.
Jon: "Hooray! All none of them!"

Peach's Castle

Right off the bat, the introductions.
Stephen: "That's right, it's that time again. Fortune Street, here on The Runaway Guys. With our faithful friends, Emile..."
Emile: "Ah...!"
Stephen: "Jon..."
Jon: "Waaaaaaaaaa."
Stephen: "Tim..."
Tim: "BABYICOMPAREYOU TOAKISSFROMAROSEONTHEGRAY!"
In the first half, Stephen, Tim, and Jon all start listing off names of books from the Old Testament and it feels like a Big-Lipped Alligator Moment for quite a while, then becomes a Brick Joke at the very end of the game with more book names and Bible quotes.
The conversation in Part 2 about Ball Flicking.
Emile tells a story of how a pen that he brought to school was confiscated as it was advertising Viagra, a drug that he didn't know about at the time. His mother was angry because it was one of her favorites!

Pirate Ship

They start the board off with making a reference to The Misadventures of Skooks, with Tom doing a Scooby voice and both Emile & Jon doing their Shaggy impressions.
Emile: "Zoinks, we're here to solve the mystery of the Haunted Ghost Ship!"
Tom: "Roh no!"
Emile: "It's okay, Skooks."
Jon: "I'm glad he's in there and we're out here and..."
Emile: "And he's the sheriff."
Jon checks out what Tom's most expensive property is: a photography studio. Since he's playing as Slime, Tom says you wipe him on the camera to make the photos look better.
The Guys are surprised when Tom actually blocks them from getting a full row on the venture card board. They point out that this is probably the way the game is supposed to be played, but they usually politely all stick to their own row so that everyone has a chance of filling one out.
A bad pun leads to an in-depth discussion on clown fighting.
Jon: [about Tom] "Wow, he's just going for the jugular on this one!"
Emile: "...if you're ever attacked by a group of clowns, go for the juggler."
Tom: [laughs] "I love it! Dude, he's gonna be the one pelting you with projectiles, the other ones only have melee weapons."
Emile: "I guess a chainsaw is technically a melee weapon."
Tom: "He's got good coordination if he's able to keep all those balls in the air."
Jon: "That doesn't mean he can aim well, he's just used to throwing things up, so as long as you're not above him he'll never hit you."
Tom: "Yeah, but what if he's one of those jugglers who juggles with another person as well? Then he'd be able to throw 'em at you."
Tim keeps landing on Tom's comic book shop, and Tom jokes that he keeps coming back to get the latest issue of Spider-Man.
When discussing pick-up lines, Emile comes up with a pretty bad one. Tim roasts him for it.
Emile: "Hey girl, do you have Paralyze Heal? 'Cause you're stunning."
Tim: "...Not even a sniper would take you out."
[Jon cracks up]
Emile cracks a bad pun during a very tense part near the end of the game.
Tom: "Fortunately, I have enough ready cash where I won't have to sell stocks..."
Emile: "Fortune-ately?"
Jon: "Yes, don't do that right now, please."
[Emile rolls and lands on one of Jon's expensive shops, costing him over 2000G.]
Jon: "Just pay me money instead."
Emile: "OH MY GOD! JON!!"
Jon: "Pay me money instead! THIS IS THE PUN TAX! PAY THE PUN TAX!"
[Tim cracks up]

Starship Mario

As established at the end of Robbin Hood Ruins, Emile hates this board and complains about the (one) previous time he played it — then all the things he talked up to the others as being terrible turn out to be minor issues at best.
Tom, Jon, and Tim spend most of episodes 1 and 2 making funny voices while inhaling, with Emile as the Only Sane Man.
Emile: [uncharacteristically deadpan] "Meanwhile, on the side of the table where we speak while exhaling..."
[Jon laughs uncontrollably]
The video is immediately dated by the Guys discussing a), Overwatch not being out yet and b), the JoJo's Bizarre Adventure "To Be Continued" meme being a recent resurgence. These videos came out in 2018.
Jon complaining after everyone lands on his expensive spaces after he's forced to close all his shops by landing on the 'day off' space.
Emile got two Suit Yourself cards early in the game, which Jon points out is a very powerful pair of items to have, as it would let him choose at any time to bypass the loop where Jon and Tim were building up expensive shops and still level up. Of course, as anyone who's seen Emile's LPs of RPGs could guess, he NEVER uses them.
Tim winning the game. First, everyone was anxious when he leveled up and was less than 100 from winning. Then he gets enough capital to win, but still needs to loop around the board. And then, Tom lands on Tim's laundromat which cost 4205, while Tom only had 4091 in assets! Tom went bankrupt and caused Tim to win by default.
Tom: "I just really needed to do my laundry!"
After the game ends, Emile proceeds to read the 'words of wisdom'(read: loading screen tooltip) in a very stereotypical wise Japanese man voice. When he pronounces "value" as "valrue", Tom, Jon and Tim get up and leave, with Tom repeatedly screaming "VALRUE" in an increasingly frustrated tone. While Emile continues to read the tooltip out loud.

Castle Trodain

Masae jokes that she is getting killed slowly with microtransactions, which prompts Emile to bring up a Gran Turismo game that has ~$300 worth of DLC... which Jon gleefully balks at with a guessing game for how much the DLC for Train Simulator 2017 costs. The answer? $6,972 Canadian ($5,363.78 USD). And, as the comments noted, the DLC is even more by the time the video has gone up: $8,163.28 USD, or $10,604.02 CAD.
Jon incredulous response to Masae and Emile saying that "they know how he is" and that "he's scary in games", trying and failing to point out that Tim is this game's master strategist whose won the most boards. Jon ends up winning.
Jon: "Tim, this is why you always win Fortune Street. Everyone hates me."
Jon's (and later Emile's) constant mocking of Masae with "You should have bought that shop."
Masae: "I'M SORRY!"

Super Mario Bros.

This board marks their first time playing with all of the game's content unlocked, including all the boards and characters. Of the newly unlocked content, three of the four newly playable characters and three/half of the boards from Dragon Quest. After introducing them, the group decides to play on the Super Mario Bros. board, with Stephen taking Luigi. The irony does not go unobserved.
Stephen spends much of the game painting an unusual interpretation of Luigi as an Explosive Breeder. While the seeds are sown early on, it starts really kicking into gear in Part 3, when he casually references the amount of kids he's supporting, and the number keeps rising every time it comes up. First it's three, then four scant minutes later. Then five. Then he's a "Grandman!", with his family tree continuing to branch out ever further.
In the same part, the group tells a story about a chicken wing place they went to called "King Kong Wings". The image of the place on Google had an image of Donkey Kong pulled from one of the Mario Party games. Not only is it on the sign, it's on all of the windows, at the counter you order at, AND on each page of their menu.
- How this story was brought up is also pretty good (for context, Stephen had just landed on one of Emile's expensive shops and mused about potential ways to escape):
  Jon: "I don't know if I would kick a giant monkey/gorilla like DK in the nuts. I feel like that is asking for trouble."
  Emile: "Um, I have another on-topic story..."
  Jon: [incredulously] "HOW?!"
By Part 4, most of the properties have already been bought save for a few expensive shops, including a Kaleidoscope Shop in one of the M's corners which Tim has landed on — and turned down — several times. Emile lands on it, turns it down, and as Stephen rolls, Jon^note comments:
Jon: "See, that's the problem! Like, the remaining properties except for like one are just... too expensive to make it worth it." [Stephen rolls a 3] "Why is everyone landing on that spot?!"
Stephen: "I don't want to buy it, though."
Jon: "Yeah, that would be — you don't even have enough cash for it." [rolls] "Why can't I land on that spot?!"
Stephen's interpretation of Donkey Kong, the successful business entrepreneur.
Stephen: "Donkey Kong CEO of company! Donkey Kong like comic book shop! Drag nuts across comic book shop! Donkey Kong OWN comic book shop!"
Emile: "I mean, I have my own wing shop, whether I want to or not."
Stephen: "Donkey Kong like wings! Donkey Kong buy! Nuts! Hrrgh—!" [normal voice] "I assume that's how it goes every time Donkey Kong buys property."
When the Kaleidoscope Shop is finally bought:
Stephen: "Luigi likes looking at the Kaleidoscope backwards because it makes his twelve kids seem like one." [as the others crack up] "Luigi think about moving in the night. Start over. Change name to something different, like mm-hmmm-Waluigi."
Jon: [through laughter] "That's taken! That's taken, mister!"
Stephen: "Hire hitman. Take identity."
- Most things that come out of Stephen's mouth during this board could probably count.
Jon offers Emile a trade. Emile agrees... only to abruptly ask for twenty-two gold without offering any explanation as to why, merely laughing at Jon's dumbfounded reaction. Though he briefly tries to figure out his reasoning, Jon soon gives up and agrees. This comes back to haunt him later.
Most of Part 7 is tied up in one turn, as Stephen negotiates a 'Gentleman's agreement' with Tim and Emile in order to secure some monopolies. The whole process is needlessly complicated by Stephen not wanting Tim to benefit from the trade before him, leading to him engineering things so that neither he or Tim get their monopolies until he can make a final trade with Tim on his turn. ... Which he promptly forgets about until after rolling his dice, meaning he has to wait until Tim's turn comes back around.
- Throughout this, Jon decides to go into another room, specifically to sort the washing machine, since he has no part in this. While this is all going on, he can clearly be heard shouting out to the others. In particular when Stephen messes up, he shouts at him “SCOURGE OF THE INTERNEEEET!” Which Stephen said whoever backs off the deal would be called. He calls him this once more when properly returning in the next part, but Stephen is too focused on a bit, as detailed below, to retort.
Part 8 opens with a musical interlude, as the Guys step away for a moment and Stephen is left to entertain the viewers alone. He attempts to sing 'America the Beautiful', but blanks on the lyrics. Jon's return leads to some verses of 'O Canada' instead.
After landing on a pricy shop, Jon's lack of stocks means he's forced to sell shops to pay off his debt. To his utter horror, the bank's offers for his three non-monopoly shops add up to 476. He's in the hole by 477. One coin forces him to give up one of his monopolies. Yes, Emile’s specific request of 22 coins was the ultimate cause of Jon’s downfall.
- This is followed by the 'Auctions of Shame' as Jon is forced to participate in the bank selling off his shops to the others, forming 'The Rainbow District' as they each take one.
The pain train keeps rolling in Part 9, as the Rainbow District is redubbed the 'ProtonJon Memorial'. Another massive payout forces him to give up his remaining monopoly, followed by auctions that take up most of the video.
- Emile and Stephen get into a tug of war over the Toy Shop, with Stephen commenting that he's just driving up the price and intends to drop out of the bidding when Emile least expects it and saddle him with the bill. He declares this right after his latest bid, so Emile just abstains. Then Jon has to press a button to continue the Auctions of Shame Mark II.
  Jon: "I've just been reading my phone and Twitter the entire time, 'cause I am not — I don't even need to be here anymore. Part of me is like, 'I should just go to the other room and start playing Switch, completely out of view and just kinda yell, press the 2 button when I need to." [as the next auction starts] "Oh, right, there was a third one! Oh, there's four! There's four that are happening!"
- The Bakery's price tag skyrocketing as Emile and Stephen get into a button-mashing contest over it, with Tim occasionally throwing in a bid to drive the price up higher.
  Emile: "He's gonna get a monopoly if he gets this."
  Stephen: "Yeah, but how much is it worth to me? Are you willing to find out? How much ready cash are you ready to lose?" [Emile laughs] "Because I will play this game of chicken. I will play the hell out of it. This is the stuff I live for, baby. You wanna see four digits? You wanna see four digits?! This is what happens!" [suddenly stops] "When Luigi's lost everything!"
  [Brief silence as Tim absorbs that Yoshi's been left holding the 840 G bag]
  Tim: [calmly] "Shit."[everyone else cracks up in realisation and to Tim’s response]
  - Even better is that after this, Tim decides to go for the next auction. Stephen and Emile allow him, the former noting he can have it on a deal after he payed so much for the last one.
Jon's succinct summary that opens Part 11:
Jon: "And the moral of the story: Waluigi Number Useless."
Stephen: *in Waluigi's accent* "Waluigi, Number *heavily resigned sigh*."
Once Emile reaches the Bank, securing his victory:
Stephen: "I'm disappointed. You should have waited for Jon to die."
Emile: "I kinda wanted to, but th—"
Jon: [while laughing] "Wow, guys, wow! I see how it is!"
Emile: "I kinda wanted it, but—"
Stephen: [crosstalk] "This game would have been better if Jon was dead."
Jon: "No! I'm on life support right now! Do you see how tiny that man is?! He's very frail!"
- Coupled with Stephen making his usual observations about Donkey Kong's behavior.
  Stephen: "You know that this monkey just ran into the bank going AURGH! AURGH! and dragged his nuts across the floor the entire way..."
As they go to get their final tidbit of advice from the game to close out the session, Jon has his own wisdom to impart:
Jon: "Don't be Waluigi. Save your money. Have one dollar on hand at all times."
Before he goes, our guest star offers a nice wrap-up to the tale he's been weaving. Only for even that to go completely Off the Rails:
Stephen: "I just want everyone to know that this story does have a happy ending. After his success in Wall Street, Luigi actually moved back home and started to take care of all of his kids. Except for the one. Sorry, Theodore. You know what you did."
Jon: "I thought you were going to say he started an orphanage."
Emile: [as Stephen loses it] "I thought the happy ending was going to be about Donkey Kong's nuts, to be perfectly honest with you."
Stephen: [cry-laughing, voice cracking into ever higher pitches] "H-he... he started his own orphanage! With his own children!" [announcer voice as Jon and Tim crack up] "I got so many, I'm just giving 'em away! Come on down to Luigi's Orphanage! Half off!"

Alefgard

As the guest, Masae is given her pick of the remaining boards, and is torn between Alefgard and the Colossus... before realizing that the latter is not, in fact, a Colosseum.
Jon: "You just wanna fight, is what you're saying."
- She also points out that Alefgard's layout makes it look like a frog.
The roll to determine turn order leaves Emile with two, Tim with ninety-nine, Jon with nine and Masae...
Masae: "I'm second with sixteen."
When Emile notices that he's just one space shy of getting the Heart on his first turn:
Emile: "Okay, so that's that. Uh, don't want that, I would rather have — oh, I can't get the Monkey's Love."
Masae: "...What?"
A mere two episodes in, Masae manages to score the first monopoly by scooping up the last shop in District E. Amid the riotous reaction, Emile declares that he's "riding them coattails... of your loincloth." Needless to say, Masae and Jon are a little Squicked out.
Jon's remote starts declaring that its charge is running low. As he points out on the Pause menu, it looks like it's still half-charged, and they wonder whether or not this is one of those games that incessantly bugs the player to replace their batteries. Cue the pop-up reappearing while he's trying to look at stocks, blocking most of the menu.
Jon: [as the others burst out laughing] "C'mon, game, it's at fifty percent! I can't see half the numbers now!"
Emile: "You see, this is because Nintendo bought shares in Energizer, so they want to make you replace your batteries when you don't need to replace them so they make more money! All a conspiracy!"
Jon declares that despite what happened last time, he's got a lot of confidence in her in this one. Emile agrees, in his own... special way:
Emile: "Gotta ride that Masae."
Masae: "Whoa..."
Jon: "I'm a married man, thank you very much!"
Emile: "Um, um... what?"
Masae: "EMILE!" [Beat] "Whaddya mean 'what'?"
Emile: [as Tim laughs] "I'm sorry; I'm too innocent~"
Jon: [deadpan] "Uh-huh. Yeah. Should I apologize to my wife, or should you, or should he?"
Masae: "He should."
Jon: "Okay."
Emile: "I'm sorry, Reese."
Tim: "I'm so glad I'm single."
[Masae and the others laugh]
Battery Charge's reign of terror continues in Part 3, and when Jon pauses to try and point out that he still has a decent amount of energy, the graphic for P1's charge is oddly slow to load in, making it appear to be empty.
Jon: "Oh my God, please, come on. I'm gonna keep doing this each—look, Player 1 has NO battery!"
- Masae points out that there's a pack of batteries "two feet from us". Jon replies that he just likes complaining. Emile proceeds to indulge him by moving the pack...
  Jon: "You didn't even hand it to me; you just moved it closer!"
  Emile: "So now you have to look at it."
  Jon: "You moved it — it's in front of my mic; I can't even SEE it—!"
  Emile: [laughs; moves it with a thump]
  Jon: "...That's still sorta in front of my mic."
  Tim: "We desperately need webcam for this."
  [another movement thump]
  Jon: "Now I — now my leg is blocking it! Just — why are you even bothering?!"
  Emile: "You DO like complaining!"
Tim saying the word 'poots' spurs a giggle fit from Emile, which he attributes to a certain Wheel of Fortune answer. Jon and Masae naturally exploit this:
Masae: "Now I'm gonna say 'poots' at random points and he'll just start laughing."
Jon: [crosstalk over a Cry Laughing Emile] "Oh he's — he's already snorting, so..."
Emile: [semi-intelligible] "...already start with the snorting face..."
Masae: "Emile, Emile... 'Poots'."
Jon: [simultaneously] "He's in the snorting 'poots' face."
Masae: [over Emile's helpless laughter] "Wow, it works."
Emile: [rising in pitch] "I hate the way you SAY IT, Jon—!"
Jon: "Whaddya mean, like 'poots~'? He hates when I say 'poots~'." [pauses while Emile gasps for air] "It's like entertaining my nephews; it's great."
- Some time later, Jon and the others realize that Emile is still laughing, and trying to hide it by avoiding his own mic. He defensively compares it to the Buzzsaw Man Pants incident.
  Jon: "Never change."
  Masae: "Please change."
  Tim: "Not in front of us."
- Followed by Jon and Masae cheerfully harmonizing poots in order to break him.
During one of Tim's turns in Part 5, Emile observes that Jon is fond of commenting "Well, I know what you should do." On Jon's following turn, Tim returns the favor while he's debating which of three routes to take, and it quickly becomes a new Running Gag for the others to say that during his turns.
Masae and Emile tell Jon that buying a Cosmetics Boutique might "help you in the long run" in unintentional stereo, then high-five each other.
Masae: "...That was the weakest high-five."
Emile: "Rematch."
Jon: "Rematch...?"
Emile: "Uh-uh-d-d-d, she's just waving all over the place!"
[high-five redux!]
Emile: "There we go."
Masae: "Ow."
Emile: "That sounded like it hurt, but it didn't hurt me, so..."
Jon: "G'heh, therefore it didn't hurt anyone!"
Masae: [chuckles] "Ah yes, all is well and good, it did not hurt Emile."
Emile: "You know me, always selflessly thinking of others."
The laundry songs.
Emile: "I can't stand how long my laundry beeps for. It sings you, like, a one minute song."
Jon: [instantly bursts into sing-song] "Hey-you really-should pick-up-your-laundry! I'm sick offff shoveling it! Hey-you, really, pick-up-your-laundry," [winding/dropping down into a more conversational monotone] "I'm so sick of this."
Tim: [semi sing-song] "Hey, you, pick up your laundry, and make sure you clean out the lint!"
Jon: [sing-song] "Stop putting receipts in the laundry!"
Masae: [softly, building up] "I hope you didn't want that twenty-dollar bill!"
The episode-naming discussion in Part 7. After Masae comments on Emile's irrelevance, Jon points out that he's actually in a Kingmaker Scenario: if he bankrupts, it's Game Over. And the other three are close enough that any one of them could potentially win based upon whose space takes him out.
Emile: "What a great honor: choosing whoever wins the game that's not myself."
As Jon negotiates a series of trades with Masae and Tim:
Jon: "Well, everyone in this ridiculous trade gets a monopoly out of it."
Emile: [softly] "Hi."
Jon: [louder] "Everyone in this trade."
- Jon calls Masae by her real name Shauntelle during this process. The comments notice.
After Masae lands on a safe spot between one of Tim's monopolies:
Emile: "How do all of you constantly thread every needle?"
Jon: "It's... it's actually kind of obnoxious—"
[chaotic crosstalk]
Emile: "—Like I, I miss all of the threads for you guys."
Emile's admission about Stranger Things:
Emile: "Up until, like, middle of this year^note2018, when the video was recorded, I thought Stranger Things was a Disney Princess show."
Tim: "Oh, man. Well."
Emile: "'Cuz I'd only ever seen the title, and I was thinking it was like 'Oh, stranger things have happened... you know, like them wanting a boyfriend?"
Tim: "Ohhhh, yeah."
Jon: [strained] "...Okay, I can guar—I can definitely tell you that's not what it's about..."
- ...Which leads into another confession:
  Emile: "Up until a couple years ago, I thought Stephen King died, like, a hundred years ago."
  Jon: "Over a hundred years ago?!"
Emile finally catches a break and rolls what he needs to land on the last shop required for his first monopoly, which he realizes only after committing to a different direction.
Emile: "I get to play Round the Blocks, whoopie--!"
Following Emile making a big payout to Tim, including a hefty comission:
Tim: "You didn't have to help me that much." [others laugh] "I appreciate it, though."
Emile: "You're welcome."
Masae: "How does it feel to be a feeder, Emile?"
Emile: [as Jon breaks down] "What's a feeder?"
Masae: "You're just feeding everyone..."
Emile: "Oh. At first I thought you said 'How's it feel to be a theater?', and I'm like 'Are you making fun of how no one likes going to the movies anymore' and..."
Jon: "No, it's a different kind of making fun of."
Tim attempting a Mickey Mouse voice leads to a spate of impromptu impressions of Mickey, Goofy and Donald, before Emile busts out "They'll pay for this" and Jon straight up loses it.
Jon buys out one of Masae's shops. It only cost him 350G because Masae never upgraded that shop. His move ends up helping the others in the long run as they keep landing on her other shops in that district.
- To add insult to injury, the shop in question is the very same shop that Masae had received from Jon in the aforementioned three-way trade!
The kill-shot, and the uproar that follows as Emile fulfills the prophecy and becomes the second player to Bankrupt. Mainly because it was only a kill-shot because Jon had just spruced it up. Jon's luck destroyed Emile this time. Fitting, given Emile's expressed desire to twist the knife and see him bankrupt last round...
Emile: "I'm punching the shop that killed me!"
- While reviewing the results, Emile notices something that really drives home their difference in fortunes this time:
  Emile: "Jon's total sales are like equal to my total payout!"^note
The end of game advice? 'Keep buyouts at bay!' Apt in this case, due to Jon sniping the weakest link in one of Masae's monopolies earlier, which helped cost her the game and prevent her from being the first guest to win... yet again.
Masae: "Screw you!" [others laugh] "Screw you, game!"
Jon pointing out that he never actually had to change the batteries after all.

Bowser's Castle

Tom changed his character from Slime to Jessica. However, he claims he's still Slime, he just had a makeover.
Tom: [as the dramatic opening sting of Bowser's Castle plays] "I'm...BEAUTIFUL!"
Emile ends up telling the same story about the Viagra Pen that he did in Peach's Castle.
At the beginning of episode 3, Jon talks about getting the Guys their own theme song to play at the ends of their videos. Tom sings his own TRG theme song that he made up on the spot, and he and Jon jokingly say to put that at the end of the video. At the end of the video, the song plays again.
After wondering what the Canadian equivalent of Uncle Sam is, Emile starts brainstorming 'Mountie Jim'. Whom he describes as having a tall red hat, a mustache, a nose that's kind of shiny due to the cold weather...
Jon: "You're just describing Santa Claus!"
Jon's first card pull forces everyone else to move a single space forward. This triggers Tim getting a new card of his own — one that grants him an instant promotion.
Jon: "Ho-why?! Why did everyone benefit from my misfortune but me?! ...I think that's my brand!"
- This is followed by them rediscovering that Jon wasn't affected by the card, as he proceeds to roll a two — the lowest he could have gotten without getting a one like everyone else.
After Emile casually observes that Jessica is 'so cute when she's dangerous', then starts joking about how, if Dragon Quest has attractive women in it, he should look into it more.
Jon: "You're very lonely, aren't you?"
Emile: [softly] "Yes."
Jon: [laughs] "And yes, Dragon Quest is a great series. And yes, it has women with your kink."
[Tom wheeze-exhales over Emile's "Whoa..."]
Jon: [cheerfully] "There we go; just gonna throw that out there~"
Are we not going to talk about the hilarious parody of Sweet Caroline in part 5?
Jon: "Fortune Street!"
Emile: "Extortion!"
Tom (I think): [amid laughter] "Stock! Stock! Stock!"
Jon: "No one can afford to live here!"
Tom: "Can't live! Can't live! Can't live!"
Jon: "Someone's going bankrupt!" [amid more laughter] "Bum-bum-bah! Will it be the monkey-"
Jon and Tom: [simultaneously] "Or the dino?"
In episode 5, Tim plays Memory Block. Jon jokes that Tim should pick one of the small blocks (which all give negative 'rewards'), with Tom saying that he should pick 'the third one'. He does.
Emile marvels over the fact that Jon has more video games than he does unique Pokémon cards.
Emile has only one request of Donkey Kong before a critical roll: "Don't roll a four." Naturally, he does. Cue Tom cackling with unbridled glee while the rest of the Guys freak out.

Good Egg Galaxy

Emile opens the board with a bizarre accusation:
Emile: "Tom, you stole her boobs; those are the source of her power."
Tom: [slowly] "...Whose... boobs... did I steal?"
Emile: "I-I meant to say Jon, you stole Rosalina's boobs; those are the source of her power."
Jon: "No, no, I multiply them. Tenfold."
Tom: "Tenfold!"
Emile: "Well, she did a good investment by giving them to you."
Jon has to explain the Alt-Jons/Joniverse from his streams to Emile. Namely because, after wondering who Tim would be (and learning that he's already been drawn as Pauline), he laments having to BE Daisy rather than having Daisy.
Jon: [regarding the sheer amount of Alt-Jons out there] "I have literally stopped counting."
- Tom comments during this sequence that he himself had been drawn as Tharja.
History Repeats itself as both Jon and Tom are competing for districts adjacent to the bank. Jon is not amused.
The "Rolling an H" gag returns again as every time one of the Guys rolls a 7, they'll shout "PUT IT IN H!" Since this is a larger board, there are a lot of Hs.
Tom's response to Emile dominating the yellow district leads to some confusion:
Tom: [in a horrified elderly voice] "It's the end of the world! Emile has a monopoly!"
Emile: "Were you trying to be Uncle Pennybags?"
Tom: "F-from Monopoly? I don't think he says it's the end of the world when somebody has a monopoly!"
Jon: [in a similar voice] "Everyone's doomed! Someone's successful!"
After landing on one of Tim's spaces, Tom wonders what he bought, but isn't able to check what kind of shop he's standing on. As he laughs about the concept of buying something sight-unseen, Emile checks for him and discovers that it's a barber shop.
Jon acquires the board-specific catchphrase "I HATE EVERYTHING ABOUT THIS!"
Jon: "If I somehow come back to win this, this will be the most cathartic board in history."
Tom: "I will be upset if you come back and win this, and you're not jumping in my face saying 'Boo-yah, motherfucker'. I'll be upset if you don't do that!"
Jon: "Okay. Alright."
Emile: "Express permission granted." [Beat] "Did I ever tell you guys about the time that I had the express permission of a charity to pee on their property?"
Jon: "See, for us this happened like three days ago—!"
Tom: [lands on the heart] "YES! [laughs maniacally as he blocks Jon's line, swiping what he would have gotten for his next venture - a chance to warp directly to the Bank.]
Jon: "I HATE EVERYTHING ABOUT THIS! I HATE EVERYTHING ABOUT THIS!"
Tom: "I'm getting money!"
Tim: [calmly] "Well, that sucks."
Emile: "I'm glad I don't have to explain my story anymore 'cause that just shifted all the attention away."
Tim's reaction when Memory Block comes back up for Jon:
Tim: [quietly] "Oh my God, never again."
As Jon and Tom prepare to trade shops and shore up monopolies:
Emile: "Tom, Tom. Request like two gold from him."
Jon: "NO!" [Beat, then completely calm] "I have trauma from that still, if you couldn't tell from how loud I just yelled no."
Upon landing on Tom's most expensive shop in Episode 4, Jon refuses to press the button until Tom looks at him Flipping the Bird, complete with Tranquil Fury.
Emile lands on venture spaces ridiculously often, meaning (despite Tom's chaotic attempts to block their lines as usual) he covers more than a third of the venture space grid in yellow by himself.
- Reaches its peak hilarity when Emile randomly makes a diagonal line, with none of the involved realizing that was a legitimate way to make a line in the venture board.
Tom sings about hypothetically landing on a bad spot to the tune of 'Sweet Caroline', with Jon taking that and running with it:
Tom: "IIIII'd lose my lead!"
Tom and Jon: "Bum-bum-bah!"
Jon: "He's gone and killed himself here!"
Tom: "I'm dead! I'm dead! I'm dead!"
Jon: "Noooo more fun! For-him-now!"
Tim: [simultaneously] "Ohhh my God! Take a dump!"
Jon: "'Cuz he's in the lead except he's choked now! Now he's in last, bum-bah-bum-bah~ And everyone else is happy! Or maybe it's just me 'cuz I'm sick~! He's twisted! He's twisted!"
Tom: "Meanwhile, this is like — this is a dream sequence and you're like, passed out on the floor 'cause you got so angry."
Jon: [laughs] "I just had a rage blackout."
Tom constantly admires the chaotic mess he made of the venture board, expressing a desire to see what happens when it's completely filled out. Come the climax, he actively moves away from the Bank despite being primed to win, simply to give them a chance to claim those last few squares and see what happens... and promptly ends up stumbling back into the loop.

Funny / The Runaway Guys Fortune Street

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Funny / The Runaway Guys Fortune Street

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