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  • The Poké Ball option from Diamond. The binary code even translates to "fear Missingno."
    • Picking the crowbar results in Henry being pounced by a group of headcrabs.
  • In Airship, the face the guard gets when you use Mind Control. His eyes drift off to the sides of his face like he's absolutely spaced out.
  • The Charles option 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 LQL (Lightning-Quick Larcenist) ending of "Infiltrating the Airship". 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 G facepalms while an agent slowly raises an assault rifle at the dumbfounded Henry.
  • Making an animal noise to Charles. Doing this will give you the "Barnyard Blitz" medal.
    Charles: Alright, I've hacked into their power grid. What do you want me to do?
    Henry: [Sheep noise]
    Charles: Okaay... I-I don't understand what that means.
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    • In that same event, if you choose "Reroute the power", the power for the obstacle is rerouted to a room where a Mook is developing photos. It's unclear whether the resulting scream is a scream of pain because of the bright light in his eyes, or a Big "NO!" because the photos were overexposed (and therefore ruined). Either way, it's funny.
  • A lot of the failing options are quite hilarious.
    • Stealing the Diamond:
      • Trying to snap the final guard's neck in the undetected path results in Henry falling down a nearby flight of stairs. Trying to shoot him with his own gun doesn't work because Henry misses every single shot.
      • Henry's attempt to do a Falcon Punch in Stealing the Diamond results in nothing happening because he's not a superhuman capable of doing the Punch.
      • 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.
      • Attempting to jump and run with the diamond at the last leg of the game results in Henry Letting the Air Out of the Band as he drops to the floor with the extremely heavy diamond.
      • During the Epic ending, 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 does a Divide by Zero and causes the fabric of reality to disintegrate.
      • During the Undetected path, Henry has to find a way past some guards with the diamond in tow... or he can just eat some cheese.
        FAIL Screen: Wha-W... Why..? ...Seriously..?
      • In the second Sneak option (going through the wall), 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. Henry's expression is what sells it.
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    • Infiltrating the Airship:
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    • Fleeing the Complex:
  • On the flip side, some of the correct options are also pretty funny.
    • In Airship, Grappling Hook route, one gap crossing section has a leap option. Henry jumps into the air and gets carried over because the pilot had to pull some evasive maneuvers at that moment.
      Airship pilot: My apologies everyone. Have to deploy some evasive maneuvers. Flock of ducks flew by.
    • The aforementioned "reroute the power" is also the correct option at its branching point.
    • In Diamond, one option to sneak in is to use a pick. Henry starts chipping at the wall, and then a Creeper comes out of nowhere and blows up the wall.
    • In Airship, using the Spook option merely causes the records-holding guard to greet the fake spider with kindness. Henry just knocks him out with the stick instead.
    • Also from Airship, Henry has to get past some Slow Doors threatening to close him off from the Toppat Leader. He eats some beans and uses the ensuing superfarts to boost past the doors.
    • In Complex, two guards are chatting in front of a door. Henry gets them 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 towards them.
    • Also in Complex, 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.
    • Also also in Complex, when Ellie is captured by Grigory, Henry can make a face. Both Ellie and Grigory will give him a "Ugh, are you serious?" glare, but it works anyway as it distracts Grigory long enough for him to get accidentally bunked by a speeding jeep.
      Ellie: Thanks... I guess?
  • 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). In Infiltrating the Airship, it teleports him into some kind of white void. 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.
    Protoss Colossus: leave noob
    Fail Screen: gg no re
  • Another humorous running gag are 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? Gadget Gabe admits that the Shadozer is not that good, so it's very easy to be Wrong Genre Savvy and assume that this one will succeed.
  • Every option available in Breaking the Bank. They all end in a very humorous failure. Special mention goes to the disguise option, which gets Henry into the bank vault. Unfortunately, he activates the bank's security system as soon as he escapes the bag. Oh well, better luck next time.
  • In Fleeing The Complex, when Henry's with Ellie, he decides to distract the guards by dancing. Everyone then proceeds to join in, including Ellie. She was probably supposed to attack the guards, but she got distracted.
  • One of the fails in Complex has Henry accidentally shoot Ellie in the head with a sniper rifle. Sounds sad, right? It is, until you click on the instant replay text and get this.
  • During the Charge Tackle route, Behind the Truck segment — one of the options is to disguise yourself as a snowman. This wouldn't be gut-bustingly hilarious if it weren't for a guard's reaction to seeing Henry:
    • At the same 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.
      FAIL Screen: That wasn't scary...
  • During the Toppat Route, one of your options is to have an undercover agent from the Toppat Clan escort Henry to the ship. He's not very stealthy about it.
    Agent: (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.
  • Near the end of the Boost Up-Ellie 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?
  • One option in Complex when Henry is behind two guards is to pickpocket one. He 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 more funny is the fact that the guard he pickpocketed doesn't even notice that Henry stole his weapon and shoes.
    • Clearly, Henry had a Pickpocket skill of 100.
    • Even better, after Henry collapses from the excess loot, the spearman looks down at his hand, just now noticing his weapon isn't there.
  • Many of the Gone Horribly Right Fails are absolutely hilarious. For example:
    • In Airship, Charles shoots the guard with a gatling gun. He kills the guard, alright... and Henry.
    • In Complex, Henry uses a box to hide from the guards. They end up using him as a poker table.
    • Also in Complex, 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.
    • Yet another Complex one has Henry use a Magnet to pull the Toppat airship closer to him, so that he can board it. He succeeds... by making the airship crash against the entire Complex.
  • The Henry Stikmin Collection gives a new FAIL to the shovel option in Bank: Henry pulls out a shovel and digs straight down, only to encounter and puncture something solid underground. He pulls out his lighter to get a better look at it, which is revealed to have GAS MAIN written on it. Guess what happens next.
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