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The series where it's almost as good, if not better to fail than to succeed, and here's why.


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General:

    Running gags 
  • The teleporter that Henry keeps getting. In Crossing the Pit, it teleports him into the pit. In Breaking the Bank, it teleports him into the wall, leaving him stuck in it. In Escaping the Prison, it teleports him into a police training ground, where he gets shot. In Stealing the Diamond, it transports him into the air above the museum (three feet above the museum, but Henry still got a scare out of it. The remaster puts him way higher, but it still works anyway). In Infiltrating the Airship, it teleports him into some kind of white void of nothingness. In Fleeing the Complex, it teleports him to the Starcraft universe, where he ends up in the middle of a group of Protoss Zealots performing a doomed Zerg Rush against a Protoss Colossus.
    FAIL Screen (Bank)note : It's emergent technology. I'm sure it will get better!
  • Another humorous running gag is the various gadgets reviewed by Gadget Gabe. Every single one of them works exactly as advertised… but never in a way that actually helps Henry.
    • The Opacitator in Prison makes its user intangible and capable of passing through solid objects. When he uses it, Henry falls through the floor… and then all the way to the center of the Earth.
    • The Liquidificator in Diamond turns its user to liquid. When Henry liquefies himself, he just splashes to the ground, unable to do anything.
    • The Transdimensionalizer in Airship allows its user to visit alternate dimensions. Henry reduces himself to one dimension and is unable to flip the switch again due to limited movement.
    • The Shadozer in Complex turns its user into a shadow... thereby leaving them incredibly vulnerable to being wiped from existence when the light source is covered by clouds.
      • The real kicker? While Gadget Gabe lampshades it by admitting that the Shadozer is not that good, it's very easy to be Wrong Genre Savvy and assume that this one will succeed.
    • Four of them in Mission:
      • The Infini3 is a cube that can store anything, no matter the size, and is said to have infinite storage. Problem is, after Henry loads one single item in it, it becomes full and has to make room by releasing an entire ship. It has infinite storage, but only for one item. The Fail Screen berates Henry for buying it used.
      • The Leafmöde can turn any object it touches into a leaf. Henry accidentally drops it on the station's floor, turning the whole thing into a leaf, leaving him trapped inside.
      • However, the SuccPak works as intended, sucking all of the Toppats' goods into a pack. The description says, "It certainly does suck!" even though it works extremely well.
      • That also applies to the Swapper.note 
  • The Charles option from multiple games, starting from Airship.
    Charles: Alright, here I come! [singing] Dah dah darrah dah darratatatataaa! [cut off by FAIL]
    FAIL Screen: Hey, look! Charles is here!
  • The FAIL Screens constantly referring to Henry as fat, fatty, fatso, and so on every time he falls off due to his weight. And the irony is, Henry isn't fat. His weight in the trailer of Complex is listed at 110lbs/50kg. The FAIL Screen only calls Henry fat just to take the piss out of him. That or it's another Call-Back to Crossing the Pit, where the original fail involving the plank made it break at the middle point due to Henry's weight.
  • Henry's absolutely horrific aim any time he picks up a gun or any kind of projectile weapon. The only time he hits his target with a gun is when he does a 'super precision shot' to steal the rocket in Stickmin's Space Resort. Otherwise he can't hit the broad side of a barn. He misses every single shot with an automatic rifle in Stealing The Diamond. Misses four shots that have a 95% hit rate and bounces a cluster of bombs that return right back to him in Completing The Mission. Shooting Ellie with a sniper rifle by accident in Fleeing The Complex and worst of all, letting a grenade roll right back to him, blowing him up in Escaping The Prison. All of these are so improbable they're hilarious.

Pre-Mission games:

    Breaking the Bank 
Fails: Well, Failure Is the Only Option, after all...

    Escaping the Prison 
Sneaky Escapist/Sneaky Ending Route:

Lawyered Up/Legal/Lame Ending Route:

  • The ending. Henry walks out of the courthouse and takes a deep breath... only to immediately go chasing after a passing armoured car. He only took a few moments of being cleared of all charges to go right back to criminality!
    • Even better? He's chasing after the car on foot, and somehow managing to keep up with it!

Badass Bust-Out/Badass Ending Route:

  • Choosing to try and turn a corner when running from the guards will result in Henry randomly tripping and falling on his ass.
    FAIL Screen: lol Brawl reference! :D
    Achievement Unlocked: lol Brawl Reference

Other:

  • Choosing the rocket launcher at the beginning has Henry fire a rocket out of his cell. However, it redirects back to him after going through a U-pipe and makes contact with him in the eyes before exploding.
    FAIL Screen: Uh... way to aim, buddy.
  • Shawn Sean's bio is this in comparison to most others:
    This is his first day back from a nice vacation.

    You ruined it.

    Stealing the Diamond 
Intruder on a Scooter/Aggressive Ending Route:
  • Henry's attempt to throw a sticky Plasma Grenade at a helicopter-riding Sniper results in the grenade getting stuck to his hand before it explodes. There's a reason sticky grenades are usually shot from launcher guns after all...

Unseen Burglar/Undetected Ending Route:

Just Plain Epic/Epic Ending Route:

  • The correct option to start this route is to use a pick. Henry starts chipping at the wall, and then a Creeper comes out of nowhere and blows up the wall.
  • Then, once he's in, you can have Henry grab a gun and try to use it on the guards, only for it to turn out to not be loaded, as it is only a museum exhibit. Henry's expression (reminiscent of Rage Comics' "Poker Face") is what sells it.
  • In the exhibit adjacent to the Tunisian Diamond's:
  • After you use the Mushroom option, the perspective switches to the Center for Chaos Containment, where one of their employees is tasked with dealing with the crisis Henry unleashed in the museum. One of the options drops a little calculator, that spells out "1337" to a pleased Henry. Then, it divides by zero and causes the fabric of reality to disintegrate.
  • Another option for the CCC is a Kill Sat with Shoop Da Whoop's face on it.

    Infiltrating the Airship 
Government Supported Private Investigator Route:

Relentless Bounty Hunter/Rapidly Promoted Executive Route:

Pure Blooded Thief Route:

  • The start of the route has the expanding foam option. Henry shakes a can of expanding foam to try and open the door, but it doesn't work. He then tries again, only for the can to explode, causing a big foam cloud to form.
    FAIL Screen: I think it said do NOT shake well.
  • Henry getting distracted by the Toppats' copy of Civilization V. The kicker is Cuppa Joe's unamused expression upon catching Henry.
  • The gap crossing section has a magic pencil option. Picking that will cause Henry to draw a creature (presumably intended to be a hang glider)… which promptly hits him right between the legs. The fail screen calls that thing a "Nutshot Crawler".
  • The correct choice in this section is just… to leap across. Henry jumps into the air and gets carried over because Reginald had to pull some evasive maneuvers at that moment.
    Reginald: My apologies, everyone. Had to deploy some evasive maneuvers. Flock of ducks flew by.
  • If Henry tries to open the vault door with a Power Glove… absolutely nothing happens. At least Dave finds it hilarious.
    FAIL Screen: You look like an idiot…
  • One of the final choices is a propane tank. Henry tries to use it to get off the airship, only for him to be blasted off and blown up while the Toppats just look on in disbelief.
    FAIL Screen: Hank Hill Quote

Other:

  • The Lightning-Quick Larcenist "ending". Henry makes off with a safe from the Toppat Clan's hold. The ending shows the agents congratulating him and opening it. There's nothing but a teddy bear in it. Captain Galeforce facepalms while Rupert slowly raises an assault rifle at the dumbfounded Henry.

    Fleeing the Complex 
Ghost Inmate Route:
  • Henry gets Isaac Binderson and Heath Stone out of the way by making them fight over who farted, when in reality he simply tossed a whoopee cushion with a rock tied to it on the floor.
  • One of the fail options for this part is trying to pickpocket one of the guards, specifically Isaac. Henry winds up taking the guard's spear, shoes, gold coins, a silver ring, a PDA, a receipt for Gamestop, candy, Spell Tome gas, a 10-pound weight, and one of Monstro's teeth. Unfortunately, the bag is carrying too much stuff and flattens Henry. What makes it funnier is the fact that Isaac doesn't even notice that Henry stole his weapon and shoes.
    • Even better, after Henry collapses from the excess loot, Isaac looks down at his hand, just now noticing that his weapon isn't there.
    • Clearly, Henry had a Pickpocket skill of 100.
  • If Henry tries sneaking out of the complex on his own, he has to get down an elevator shaft. If he tries bungee-jumping, he ends up separated from his torso. That's kind of what happens when your bungee cord is a normal rope…
  • In the Docks segment, Henry can use a box to hide from the guards. They end up using him as a poker table.
    FAIL Screen: Hey at least you weren't found!

Convict Allies Route:

  • If Henry and Ellie try to use the "Tall Guy" maneuver to get past Isaac Binderson and Heath Stone, they look at each other and instantly prepare to apprehend them.
    Henry: Hey buddy.
    (The two guards just proceed to point their spear at the duo afterward)
    FAIL Screen: I don't see how being taller was supposed to help there.
  • Another option is to distract the guards by dancing. Everyone then proceeds to join in, including Ellie (pictured above). She was probably supposed to attack the guards, but she got distracted.
  • Another one involves the two using the Bounce Bros. Which they proceed to botch almost immediately.
    FAIL Screen: Did you really need to be so extravagant?
  • If Henry and Ellie choose to try a judo throw to scale a wall, Ellie anticlimactically slings Henry face-first into the wall with an audible SPLAT.
  • In the Hallway Standoff segment, if you choose Henry with a sniper rifle and Ellie with a taser, Ellie turns and shoots Henry with the taser, which results in Henry firing wildly and shooting the guards by sheer dumb luck.
    • One of the fails in the Hallway Standoff has Henry accidentally shoot Ellie in the head with a sniper rifle. Sounds sad, right? Well, until you click on the instant replay text and get this.
    • Another fail happens when Henry throws a grenade at the guards while Ellie fires a crossbow that results in the grenade getting stuck in one guard. Realizing what happened, the guard jumps toward Henry, ready to blow him up too.
    • The fourth combination is no less hilarious as Henry throws a grenade at the guards and Ellie hits the grenade midair with a tazor. The resulting explosion somehow blows apart several floors of the complex. Lampshaded by the Fail Screen.
  • After that, Henry and Ellie try to sneak out of the complex by disguising themselves as guards. They end up getting attacked by a group of convicts.
  • When Ellie is captured by Grigori, Henry can make an ugly face for whatever reason. This leads to both Ellie and Grigori giving him an unamused glare for it, but it ends up working anyway, as it distracts Grigori long enough for him to get bunked by a passing jeep.
    Grigori: What, you think that will upset me? Oh, very mature— (gets hit by a jeep)
    Ellie: Thanks... I guess?
  • And a fail during the same moment: Henry injects himself with andrenaline and tries to Bridal Carry Ellie, but due to being, well, Henry and the fact that he's going so damn fast, he catches Grigori. After a short Beat, Grigori sends Henry to the floor face-first.
  • Near the end of this route, Henry and Ellie join people in running through a hole in the fence to escape, resulting in everyone trying it falling and possibly dying since they're at the top of a cliff.
    • At the same segment, escaping with Ellie and other convicts by choosing the truck is a failure because after locking themselves in the back, they realize no one is driving.
      Unknown voice (presumably Henry): Um... Who's driving?

Presumed Dead Route:

  • When you're in The Yard (Tactical), one of the possible options is entering a building. Little does Henry know that the building has Freddy Fazbear inside it. The fail screen takes the cake.
    • On top of that is the "jumpscare" itself. It's a childishly jittery and goofy-looking Freddy giving off a pathetic "eeee" noise that just can't be taken seriously.
  • During the Behind the Truck segment, one of the options is to disguise Henry as a snowman. This wouldn't be gut-bustingly hilarious if it weren't for Karl Pinkerton's reaction to seeing Henry:
    • The Fridge Horror comedy of the guard's reaction hits with two separate layers; Frosty has been incarcerated at The Wall, and Frosty was ruled as a kill on sight prisoner due to his actions.
  • In the other fail option, Henry uses a sandwich straight out of Castle Crashers to turn himself beefy. He starts curbstomping the guards until he suddenly turns back to normal as he's wailing on Gnewt Stoneheel. Henry ineffectually throws one more punch at Stoneheel, who promptly gives him a swift boot to the yam bags. Afterwards, he folds his arms with a 'so there' look on his face. Considering Henry got three powerful blows in to Stoneheel's one, that guard was much more durable than Henry was.

International Rescue Operative/The Betrayed Route:

  • During the Toppat Route, one of your options is to have an undercover agent from the Toppat Clan, Wallace Pemberton, escort Henry to the ship. He's not very stealthy about it.
    Wallace: (very loudly) Henry! It's me! I'm undercover! I'm here to break you out! (notices everyone's staring at him) What?
    FAIL Screen: He spent three years undercover… What a waste.
  • The final choice in the Toppat route has an option to have Henry use a Magnet to pull himself closer to the Toppat airship, so that he can board it. Instead the magnet pulls the entire airship into the complex, causing it to crash.
    FAIL Screen: You see, because the entropy of, uh… Alright, I can't BS my way outta this one.
  • The final choice for the Government route has the option to jump off the edge. In doing so, though, Charles isn't prepared to catch Henry on account of not being informed. This results in both of their deaths.
    Charles: Did you just jump off the edge?! Wait, was that the plan? Man, we really should have coordinated that better. I mean, I was not prepared at a- (gets blown up)
    FAIL Screen: Report Charles, bad teammate.

Other:

  • One of the options at the beginning of the game is to play dead. This results in Grigori calling Dmitri on what to do before throwing Henry out the garbage chute to an actual death.
    FAIL Screen: Pretty convincing there.

Completing the Mission:

    Executive/Allies Route, Toppat King 
  • As a tense moment is shared between Henry, Reginald, and Right Hand Man, Ellie awkwardly tries to introduce herself.
    • Immediately before, Ellie asks out loud what happened to the Right Hand Man. He responds with a Death Glare that lasts for the next two scenes. The funny thing is that, due to how the scene is shot, you don't know if he's glaring at Henry for being the one who caused his injuries... or at Ellie for being rude.
  • Henry can try dealing with the government helicopter by punching it. He actually succeeds in sending it past the horizon but doesn't survive the ensuing fall by being in mid-air.
  • Henry can try to use a knockoff VATS to shoot the helicopter pilot. After four shots, each with 95% accuracy, all of them miss. That's a one in 160,000 situation right there.
    Fail Screen: 95 percent, huh?
  • Reginald will warn the guards about Henry with complete confidence for his own safety. This is hilarious no matter which option you choose.
    • If Henry abandons him, irony kicks in, both in betraying Reginald's faith, and that Henry is taken out by a Toppat clan member for riding in a government helicopter.
    • If Henry uses the helicopter, he flies straight into the tower.
      • Henry and the soldiers’ faces before his Dynamic Entry is also chuckle-worthy. Especially since Reginald is the only one who doesn’t see the impending helicopter.
    • If Henry uses the mounted gun, he shoots all of the soldiers and not Reginald out of sheer luck. This causes the helicopter to crash, since no one's at the controls. It's still the correct choice, since it puts Henry in position to deal with a bomb squad trying to disable the rocket.
  • Henry can try dealing with the bomb squad with a revolver, cuing multiple bullet time reticles to appear over the guards. One problem: The guards themselves are still moving in normal speed.
  • Henry can try stunning them with a boomerang. It comes back and stuns him, too.
  • Henry plays a flute. He's really bad at it, but manages to summon a couple of birds to carry him away and take the main bomb part away.
  • When surrounded by soldiers alongside the Right Hand Man, Henry can try summoning something to help themselves. He summons a moon-sized shoop-da-woop monster, but its intro sequence takes so long that everyone's long gone by the time it's ready to attack.
  • Another option in the same segment has Henry and the Right Hand Man use stylish attacks to take care of one soldier. This still leaves the rest of them, though.
  • The third option that leads to a fail in the same segment is for Henry to pull a Leeroy Jenkins and charge at the soldiers while yelling "Henrrrry!" Cue a soldier immediately gunning him down.
    Fail Screen: Oh my god, he just ran in.
  • If Ellie tries to take care of Hershell (the armored mook blocking their path) by shooting them, the car swerves off the bridge to their doom, since Ellie was the one driving.
  • If Right Hand Man tries to boost them forward, he puts a bit too much energy into it, going right through the ship.

    Bounty/Ghost Route, Free Man 
  • Henry can try to swing over to the remote to open his cuffs. He ends up ejecting himself instead. At least he proved he wasn't the imposter!
  • Henry can try using his inner strength to break the cuffs. This only succeeds in tiring himself out.
  • Henry can try using a thunder spell to overload the cuffs, and zaps himself in the process of breaking the cuffs.
  • Henry can try picking the lock to his door... except for the fact that the door doesn't have a lock. If you do this over and over again, the game will get more and more annoyed until it finally caves and gives you a lock to pick… only to come face to face with an armed mook.
    There is no lock to pick...
    There is still no lock to pick...
    You gotta stop trying this, man.
    THERE. IS. NO. LOCK.
    Hgnk!! Frrggghhhh!
    Fine!? You want a lock?
    THERE! There's your lock!
    Fail Screen: You should've just moved on to something else...
  • Henry can try using a melt ray to melt the door, but the melt ray just melts itself.
  • Henry can try to blast it open with a bomb... until he realized that he can't stay away from the explosion due to being in a small cell and blows himself up in the process. At least the door is open!
    Henry: (Beat) Wait...
  • In the armory, Henry can grab a big sword to deal with the guys outside. He takes one out, only to lodge the sword in the ground, leaving him a sitting duck.
    Fail Screen: That's a big boy sword. For big boys only.
  • He can deal with them with a grenade launcher, only to blow a hole in the wall, sucking them all out into the vacuum of space. The FAIL screen will even wonder why the Toppats even had a grenade launcher on their space station, given the obvious problems with using it...
  • The fact that the correct choice is a NES Zapper (labeled as a pew pew gun) is funny. The fact that he proceeds to tear through everyone else in his way with it (until he gets to Right Hand Man) is hilarious.
  • Right Hand Man has Henry down. Henry can try sweeping his legs, but does little more than hurt his shin against RHM's metal legs.
  • Henry can use Harden. This barely slows down Right Hand Man, as he breaks Henry's head open like an egg.
  • Henry can launch a rocket at Right Hand Man. This actually works, but Henry forgets to release the rocket from his nano-suit.
  • Henry can try hijacking a satellite to attack the base with. If he picks the yellow one, he'll realize too late that it's a communication satellite.
    Burt: We're picking up a data stream from our broadcasting satellite.
    Right Hand Man: You don't say...
    Burt: Yeah, it just keeps saying "attack attack attack, fire, shoot the laser..." (Beat) Oh, hang on...
    (Cut to Henry already killed by Right Hand Man)
    Burt: It just stopped.
    • If he picks the rocket-shaped one, he'll use it to fire a laser. Except the end that opens up is for the back draft. Henry just nuked some random place on Earth, and Right Hand Man is just staring at him like even he can't believe how badly Henry screwed up.
    • If Henry tries going directly back to Earth, he finds out the hard way that his nano suit doesn't protect him from burning up on reentry. The last scene before the FAIL Screen is of Henry's blackened body falling out of the sky.
      FAIL Screen: Toasty!

    Government/Rescue Route, Special BROvert Ops 

    Government/Allies Route, Triple Threat 
  • Henry and Ellie can parachute right into the parking lot to start their mission… only to find no weapons.
  • If they try going for the control tower, they find themselves outside the tower, unable to get inside. The guy inside casually radios another guy who, after building a tower straight from Fortnite, snipes the both of them without much fanfare.
  • If they try using wings to fly directly to the rocket, they miss their mark and hit the wall, which sends them flying backwards and spiralling through the air like a pair of cheap toys. After a fade to white, it shows the two buried halfway in the ground, legs flailing pathetically in the air.
  • Ellie can grab Henry and spin him around to throw him across a gap. He goes all of a few feet before falling to his death.
  • Ellie and Henry can try climbing down and running up the ramp on foot. One problem: the ramp is incredibly long. They don't make it more than a fifth of the way there before collapsing from exhaustion. All the while, Charles awkwardly calls them to see if they need some kind of help.
  • If you keep choosing the "swap" option over and over, Charles will lightly call out Henry and Ellie while they sheepishly smile at each other.
    Charles: Hey, that looks like fun but um… Kind of… on the clock here…
  • Henry and Ellie shoot themselves out of cannonball barrels for Charles to pick them up. The results are particularly funny and interesting:
    • Missing the timer causes them to crash into the cockpit.
    • Hitting the "Hand" choice has Charles give them both a high five before they plummet to their deaths. What sells it is Charles' gleeful grin after doing that.
  • Henry can try using a "downgrader" to make everything look like a rough storyboard. Aside from disabling the Toppat goons' guns, it didn't actually offer any kind of advantage, as Henry and Ellie are still beaten senseless. Apparently, not even Henry knew what the device was supposed to do.
    Fail Screen: I guess the budget ran out.
  • Doubling as a Brick Joke from the previous game, selecting the "Diversion" option in the cafeteria would give Henry and Ellie an epic build-up song… only to begin dancing just like in the picture above once again, which naturally gives the same result as the whole clan starts to dance alongside them, with several other familiar memetic dances thrown into the mix. And since Ellie is helping this time around instead of getting distracted herself, it works!note 
    • Meanwhile, selecting the "Fusion" option causes Henry and Ellie to perform the Fusion Dance and fuse into Ellry to fight the Toppats in the cafeteria...but the fusion is no match for Kabbitz, who beats them so hard they're sent flying out of the rocket, defuse...and land in a crater in the Yamcha death pose. The Fail Screen message naturally continues the lampooning;
    Fail Screen: Normally this goes on for another 3 hours.
  • Charles tries to describe his plan to Ellie, since she's confused as to how crashing in with his helicopter is going to help. Henry agrees with Charles, so Ellie's willing to try it, but because they spent so long arguing, the rocket's already launched into space.
    Charles: Okay guys, I've got the most awesome plan. I'll crash head-first into the cafeteria window.
    Charles: No, no. With my helicopter. Whatya guys think? I'm ready t-
    Ellie: Hold on, I don't... really understand.
    Charles: What's not to understand? It's simple. I fly the helicopter into the window.
    Charles: (sigh) I don't really think you get it… Henry, you get it, right?
    (Henry raises a thumbs-up)
    Ellie: I guess I'm outvoted then…
    (Cut back to Charles, watching the distant speck in the sky that was once the rocket)
    FAIL Screen: It would've been amazing, Charles.
  • Ellie's plan is very efficient and well thought-out in comparison… or at least, it would be if Charles knew exactly what Ellie meant by the "forward-left" booster.
    Ellie: Alright guys, listen up. I got a plan. Henry and I will overload the engine room causing an explosion. Charles, we'll need you wait outside the auxiliary exhaust by the forward-left booster. We'll only have about 20 seconds to get out before it blows.
    Charles: Alright, I'll be ready. Now hurry!
    (Both Ellie & Henry proceed to do just that, only to find Charles isn't around as soon as they get out)
    Ellie: Where is he?
    Charles: Alright, I'm in position. Don't see you guys, though…
    (Cue flames spewing from the opposite side of the ship with both Henry and Ellie engulfed in it)

    Thief/Dead Route, Stickmin Space Resort 

    Thief/Ghost Route, Jewel Baron 
  • How the Toppats discover Henry's attacking:
    Burt: Hey chief? Our satellites have picked up a hostile object.
    Reginald: Oh no, is it the government? Have they sent a destroyer after us?
    Burt: Uh…
    (Toppat broadcast zooms in on Henry riding his modified scooter)
    Burt: No.
    Reginald: Well, just shoot it down.
  • Henry can make his scooter go lightspeed, except it goes zooming off without him, since he didn't hold on properly. Or as the game puts it…
    Fail Screen: You forgot to hold on to your butts.
  • After Henry succeeds in getting onto the space station by going mosquito mode, Reginald's reaction to the failure of their weapons system isn't raging at incompetence or the like, but instead:
    Reginald: Completely missed?! (sigh, pinches his nosebridge) We spent so much money on that…
  • When at the gap, Henry gets all of the options available to cross it that were available in Crossing the Pit. But the bridge fail is a standout due to just how pathetic it is. The plank Henry uses is too short! Cue it falling straight into the pit, leaving Henry just standing there looking slightly dumbfounded.
    FAIL Screen: Measure once, cut twice… wait.
  • Henry can try and wallclip into the vault to get the emerald. However, he messes up and instead falls through the floor. What sells it is Henry getting stuck in a looping falling animation and falling farther and farther into nothing as the world itself shrinks away above him, complete with the floor being invisible from below. All tropes from a game made with models, despite this game being hand-drawn.
  • If one looks at some of the items in the vault, one will note that there's a drawing in one of the chambers of the ruby that Henry stole in Airship, that also has the word "ruby" written below it. Seems like the Toppat Clan were kind of sore about losing it.
  • One of the options for getting the emerald out of the vault is to press the "Eject" button. Pressing it ejects the emerald into outer space. This begs the question as to why would there be an option to eject the vault's treasures into outer space in the first place, outside of Rule of Funny.
  • After stealing the emerald, Henry is faced with the Right Hand Man. Henry can try tossing the emerald at him. Due to a combination of the emerald being really bloody heavy and the Right-Hand Man being much further away than the guard Henry smushed with the diamond back in Stealing the Diamond, things don't go terribly well for him this time.
    • Alternatively, Henry can have a go at the infamous Chance Time. Predictably, it goes badly: the emerald goes straight back to the Right Hand Man, with him and Henry having appropriate animations for the occasion.
    • Or Henry can just yell… which just so happens to be a variation of the Unrelenting Force shout. This ends up ripping apart the whole room and sending everyone into space.
  • When faced with the Toppat Clan's Kill Sat laser, Henry has the option of going Super Henry! He does a flip, the emerald vanishes… and Henry gets atomised by the laser.

    Bounty/Dead Route, Little Nest Egg 

    Thief/Allies Route, Pardoned Pals/Toppat Recruits 

    Executive/Dead Route, Toppat 4 Life 
  • At the beginning, Henry hears of the government's siege plans from two soldiers drunk out of their minds.
  • As Henry makes his way into the government camp, Hayden, a guard, casually bets that the leader of the Toppat clan (Henry in this route) will return and screw up their entire operation. Doubles as a Brick Joke when Hayden makes good on his bet later as the government soldiers retreat after Henry, the missing Toppat leader, foils their entire operation.
  • Henry tries to get past Madd Ladd, a sniper, by running with a knife. Y'know, since running with a knife makes you go faster. This does not work.
    • Henry can try to get past Madd by eating a Duplicatorange. This splits Henry in two, with one copy falling victim to Madd. The rest of the scene plays out normally, until the FAIL screen brings the scene to an abrupt halt:
      FAIL Screen: Wait, this isn't the original Henry. We're not gonna follow some COPY!
    • Henry uses a lagswitch to get past Madd. Cue the bewildered Madd shooting Henry three times in a row as he runs in place with no visible effect, only for him to snap to the other end of the field at the third shot.
      Madd: …Did I get him?
      • This becomes a Brick Joke if you use the Hijack option next: You see Madd examining the area where Henry was, trying to find the body. And then Henry runs him over as he goes careening off the cliff.
  • One of the options for hijacking the Big Boy tank is to watch a walkthrough… which involves Henry watching a Let's Play of his own game. That alone would be funny enough, but it's a Fail, because the Let's Player is so incredibly bad (a look at the like/dislike ratio will reveal that the video has 4 likes to 35 dislikes) that not only is Henry not helped, he ends up being stuck in a loop of watching the video ramble on while choosing the Walkthrough option over and over, until the player gets bored and clicks out, at which point the Fail Screen reveals a running tally of how long you were watching it.
    • It's noted that while the footage is clearly in a loop, the scrolling of the timer essentially gives the illusion that the whole thing is part of a greater fail and there is a punchline and/or achievement at the end (there isn't), unaware that the loop is the punchline. Many streamers who picked this for the first time were caught unaware and were noted to have wasted a lot of time watching this fail alone. One player decided to test how long it can go by putting a 15 hour version of it.
    • In fact, the achievement is to click out of it as fast as possible, meaning that all of the YouTubers and Streamers were wasting their time! The name of the achievement? Speed Run.
    • The cherry on top is Henry's expression on the actual fail screen, like he's silently judging you for how long it took you to figure it out.
  • If Henry tries to just drive Big Boy, he does manage to make it go… backwards and right off the cliff he just climbed up. And he forgot to signal! Sheesh!

    Bounty/Rescue Route, Master Bounty Hunter 

    Government/Dead Route, Valiant Hero 
  • When Charles tries to get Henry aboard the space station, he can try and get Henry over by shooting him over in an air bubble. Unfortunately, it moves so slowly that Henry is dead of asphyxiation long before he even arrives at the station. All while Charles keeps casually chatting, completely oblivious to Henry's newfound corpsehood.
    Charles: It's also really sturdy, so you don't have to worry about it popping on you.
    (Henry is now seen checking his watch)
    Charles: Unfortunately, it doesn't move very fast… still working that one out.
    (Henry is choking from the lack of oxygen)
    Charles: Don't worry, I'll keep you company 'til you get there, shouldn't be a problem.
    (Henry is now dead)
    Charles: What kinda movies ya like?
    FAIL Screen: You used up all the air already? You glutton.
  • Attempting to breach the station's hull with the hot knife has it pop out of the side of Henry's helmet and drift far out of Henry's reach into space.
    Charles: (as the knife is floating away) It's a knife that's so hot it can cut through any material.
    (Beat)
    Charles: (disapprovingly) You dropped it, didn't you?
    FAIL Screen: Butterfingers?
    • Charles' earlier blunders have probably caused no small amount of exasperation to players, making the fact that Charles is exasperated with Henry for once all the funnier.
    • Side note; clicking on the text provides possibly the biggest reference to Spider-Man 2 to date.
      Butter- Pizza! (giant, screaming Henry face appears) NOOOOOO-
  • Picking Charles has the expected result. Right before Charles makes impact, Henry looks around in a panic before bracing for impact as the shadow gets bigger. The difference? This time, it isn't a fail.
    Charles: (after falling from his spaceship onto the catwalk beneath the core, where Henry already is) I've always wanted to do that.
    • Another thing can also happen. You can play the game in fullscreen mode (which makes the game crash), and play this route, if you choose Charles, he will crash the space vehicle, but before the impact happens, the game can crash and make an incredibly hilarious coincidence.
  • When aboard the space station, Henry and Charles are faced with a door blocking their escape. Charles says that he thinks he can hack it open. After a while of buzzing and typing noises, Charles turns back to Henry and shrugs:
    Charles: Yeah. I have no idea what I'm doing.
    Henry: (disapproving look)
    FAIL Screen: bruh.
  • When choosing an escape pod, one choice will have a Toppat already in it, who panics and starts mashing buttons. This activates the "reverse thruster" on the escape pod, which flattens Henry and Charles against the wall.

    Government/Ghost Route, Cleaned 'em Out 
  • The intro has Henry listen in on Government communications.
    • The value of the Toppats' stolen valuables combined, estimated by the Government, isn't an actual money value; the comms device just reads: "A LOT".
    • As soon as Henry hears of the easy theft target, he looks at the camera with the most incredible smug face. Even better, that face is his bio picture for Mission.
  • If Henry tries to get on the train by hiding in a box, the nearby Toppat goons reenact the disguise cutscene from way back in Bank… only to not be bothered to load the box, leaving without Henry.
    Filbert: How did we lose one?
    Thomas: I think we should throw it in the cart, just to be safe?
    Filbert: (Beat) ...Nah!
  • Henry can try taking a seat on the train to blend in. If he does do, he almost immediately gets noticed by a Toppat member, who asks him to move since he was saving that seat for his friend. Said friend happens to come back right at that moment, questioning why Henry is in his seat. The cherry on top of this is the expression on Henry's face when he realizes the situation he's in.
  • If Henry pretends to be a mannequin in order to avoid detection, a Toppat goon named Thomas Chipz, thinks he's a novelty coatrack and decides to have a little fun with it:
    Thomas Chipz: Woah, look at this crazy coatrack! (Picks up Henry) Oh, look at me! I'm a little hat holder person. Ooo, can I take your hat? (Leans Henry out the window) Ooooo, I wonder what's out the window? Hahahaha- (Henry gets decapitated by a passing tree branch) Awww, it broke.
    Fail Screen: Press F to pay Respects.
  • After Henry jumps out the window, he notices a tunnel approaching. If he tries to get back in, one of the Toppat goons from before will have already closed the window again. Cue Glass Smack and Slide.
  • If Henry tries using Leafmöde to collect the Toppats' stuff, he'll accidentally drop it on the floor, turning the entire shuttle into a tiny leaf.
  • If Henry tries using the Infini³ (which was advertised to house multiple parallel universes' worth of space), he'll put one helmet inside, before the Infini³ becomes full. Then, it automatically makes room by spawning a freight ship through the rocket. The FAIL Screen admonishes Henry for buying used.

    Executive/Ghost Route, Toppat Civil Warfare 

    Bounty/Allies Route, Capital Gains 
  • The route begins with Ellie abruptly stopping outside of the Wall, incredulously asking Henry why they're still riding on their dinky motorcycle.
  • The intro sequence is so over-the-top, it's hilarious. First, we get a slow-mo shot of Ellie and Henry about to crush an unlucky Quincy Tattlemuffin to death with their tank, followed by Fred Worst coming out with a turret that launches swords, all while dubstep blares in the background.
    • If they choose to fire, Fred mocks them for missing before realizing that their shot just blocked off the train tunnel. Cue Mass "Oh, Crap!" moment for literally all of the Toppats.
    • If they choose to hunker, Ellie dives straight into the cabin with Henry, which is pitch-black inside.
      Ellie: We should've just done this from the beginning.
      (CRUNCH)
      (Cut to outside, where it's revealed that the tank is now embedded in the side of a mountain, having plowed straight into it)
      FAIL Screen: Nice tank. Only way to see is to be looking out the top.
  • If Ellie tries using the force to move the cart, she succeeds… in launching it past the stratosphere. Henry's incredulous expression is what sells it.
    Fail Screen: We get it. You lift.
  • A fake option screen comes up for just a few seconds just before the Right Hand Man shows up, with the options being "Obscure Reference" (with the picture being a minimalist worm with a cigarette), "Your Suggestions" (represented by a trash can), and "Really Dumb Option" (Henry picking his nose).
  • In the final choice screen, Henry can choose to use a needle to pop the balloon holding the money cart with him and Ellie on it in an attempt to drop Right Hand Man with them… even though RHM is capable of flying, which naturally results in the car crashing to the ground with only the duo. The Right Hand Man is flabbergasted when he sees Henry take out the needle, and even remarks on what an idiot Henry was for thinking that would work.

    Executive/Betrayed Route, Revenged 
  • The fails on this route are usually as dramatic as the correct choices, but using Gun Forme against the Right-Hand Man will have him Flash Step behind Henry and rip him in two with a Kamehame Hadoken. Not funny in itself, but what does RHM say before killing him?
    Right-Hand Man: Nothing personnel, kid.
  • The Spirit Forme fail is one giant JoJo's Bizarre Adventure reference and contains quite a bit of in-jokes; the most notable being that the subtitles saying they're using "spirits", but the voiced dialogue indicates that they're clearly using Stands, and the Stands in question (Reference and Bottled Time, respectively) are voiced as Tribute and Time in a Bottle, referencing how Stand names would often be changed overseas. When Reference uses its ability, its Kiai ends up being "FAILURE FAILURE FAILURE FAILURE FAILURE". It even ends with a Suspiciously Similar Song of Roundabout, which by itself was one of the earlier JoJo memes to surface in the west.
    FAIL Screen: That doesn't seem right, but I don't know enough about anime to dispute it.
    • Anyone who can speak Japanese will be either laughing hard or scratching their heads at the hilariously terrible Japanese the characters are speaking throughout:
      RHM: Hontou ni fisuto na stop me?
    • Henry is seen smugly doing the Torture Dance as Reference prepares to kill Right Hand Man. Unfortunately, Bottled Time is not given to him by his cybernetics like Reference is for Henry.
  • On the Absorb fail, which results in Henry exploding, you can watch it again as an Overwatch-styled play of the game from Right-Hand Man's perspective.
  • If Henry picks the baseball bat against Right Hand Man Reborn's finishing move, Henry successfully bats the massive ball of energy out of the stratosphere... whereupon it goes into orbit with the Earth and completely goes around it before re-entering the atmosphere in a direct course towards Henry from behind. To add to this, the dramatic music as Henry and RHM Reborn fight fades as the energy ball gets batted into orbit, only to fade back in when it approaches from behind Henry.
  • Henry using the Airship to kill Reginald. As in, Henry literally holding Reginald in front of the Airship.
  • Henry can try to re-enact the moment where Reginald dropped him off of the airship but with their roles reversed, complete with the same dramatic music, until Reginald opens a parachute in his hat to break his fall, with him calling reinforcements to shoot Henry down shortly after.
    FAIL Screen: Looks like his hat has gotten a few upgrades!

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