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Webcomic / Jailbreak

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You wake up locked in a deserted jail cell, completely alone. There is nothing at all in your cell, useful or otherwise.
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> Start MS Paint Adventure.

Jailbreak is the first webcomic under Andrew Hussie's Troperiffic MS Paint Adventures, originating in September 2006 as a humble Interactive Comic game run by Hussie and played by friends of his on an early precursor to the MSPA forums. One of the rules of the game was that Hussie had to pick the very first suggested command for each move, no matter how unfunny or preposterous. It stars an otherwise nondescript man trying to escape a strangely built jail, which isn't rife with pumpkins.

It was left unfinished for years with Hussie stating he didn't intend to continue it, but he capped off with an ending in September 2011 during the long Homestuck pre-end-of-act-5 hiatus. Compared to its successors, it doesn't make any pretense of having a coherent world or story - it exclusively exists for and is fueled by Rule of Funny. It was something of an early prototype for the likes of Problem Sleuth, and it is the origin of many of the running mythology gags that MSPA is so famous for.

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A fan album was made by members of the Homestuck music team. Andrew Hussie's various teams for Homestuck content, What Pumpkin Studios and What Pumpkin Games, were named in honor of this adventure's running gag. Additionally, the cover art representing the adventure in Homestucknote  was eventually reused as What Pumpkin Studios' own logo.


> Search room thoroughly for tropes:

  • Anti-Climax: The game ends with the player controlling the pony and commanding it to take a nap.
  • Artifact of Death: A fairly normal tree stump (nicknamed the Suicide Stump by readers) has some sort of properties that immediately drive whoever is near it to suicide, apparently. This is demonstrated in the second route when the prisoner digs up a gun underneath the stump and is suddenly compelled to shoot himself.
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  • Artifact Title: Only in the second route, where the prisoner escapes jail fairly early thanks to an elf. The rest of the scenario is about him, some elves, and a horse.
  • Bait-and-Switch:
    • After bungling a puzzle and getting the room to flood, one of the commands issued to the first prisoner is to try drinking all the water himself. He responds with the "no/bad reply" face, declaring it the dumbest idea he's heard all day... and promptly gets on all fours and starts drinking.
    • Later on, the second prisoner is told to shoot into the hole on the roof of a building. He looks down, but when he sees the sad face of the first guy trapped in a flood, he reconsiders. He then runs a harpoon through his gut, deciding he could probably save the pistol's bullets for later.
  • Bamboo Technology: One of the two guys builds a robot out of ladder pieces called Logorg, which he later enters. Subverted when it turns out it's more "bamboo" than "technology", as it has no pieces to make it move.
  • Black Comedy Burst: The very end of the first half of the comic, which, considering how much gory comedy shows up, says a lot. After a harrowing adventure, the two prisoners leave the jail compound on a giant pumpkin. Then the first guy bleeds out, the second guy realizes his pal is dead after he tries to take his hand, and he gets so depressed he turns his trusty gun on himself.
  • Butt-Monkey: The second guy. He is repeatedly urinated on, vomited on, and has numerous ladder-based inventions destroyed. The guard has it a little worse, as he's knocked unconsious twice before he meets his demise.
  • Combinatorial Explosion: Parodied. There's plenty of flavor text for item combinations, like singing a random song or hypothetically placing your head in a wooden robot, but sometimes simple acts such grabbing a pumpkin will be denied.
  • Comic-Book Time: The guard's rotting head and pumpkin were noted to have been buried for days, despite what seemed to only be a few hours' difference from getting his head cut off at most. Other than this, not much time appears to take place between commands.
  • Cut Short: Jailbreak was unfinished until September 2011, where the ending was written after at least a five-year hiatus. That's got to be some kind of a record.
  • A Date with Rosie Palms: The main prisoner suddenly feels the need after messing around with a drill.
    All these thoughts of drilling and penetration have given you a serious hankering for some quality time with HUNK RUMP magazine.
    > Continue to enjoy Hunk Rump.
    (We are now in control of the other guy.)
  • Delayed Reaction: Not all the commands are responded to in time. Sometimes one of the prisoners will ignore the order until the exact time Hussie could use it to screw something up.
  • Desecrating the Dead: The overkill the guard goes through. Getting his head bashed in was bad enough, but then his body was mangled by a drill and what was left of him was used as makeshift escape rope. And the worst part? Some of these actions were by accident. At the very least, his head getting cut off and put in a pumpkin was the first prisoner's weird way of giving Due to the Dead, but even then he later cuddles it and was seriously considering eating its makeshift coffin. (Our hero is...out there, to say the least.)
  • Dissonant Serenity: When the second guy climbs up into the first prisoner's room, he takes one look at the gory remains of the guard and cheerily tidies up the place.
  • Downer Ending: Averted thanks to a quick press of the Reset Button.
  • Early Installment Weirdness: "He already has arms, stupid!" is introduced as a gag here, but unlike the "Retrieve arms from [X]" variants seen starting with Problem Sleuth, we get this batshit command instead:
    > Grow two muscular arms with which to manhandle the key.
  • Eats Babies: The elf in the second part is willing to break the main character out of prison when he promises it a baby, represented in thought as lying on a plate with an apple in its mouth.
  • Expressive Mask: Averted; the Pumpkin Helmet does not change shape to match the face of the character unless it is physically twisted from its frowny face to its smiley face. At one point it gets stuck halfway between the two.
  • Fantasy Kitchen Sink: For no reason at all, elves feature in the story.
  • Featureless Protagonist: Other than the fact that he is male (and perhaps androsexual), the main character has absolutely no distinguishing features whatsoever.
  • Finagle's Law: No matter what helpful things the characters do, something inevitably goes wrong during the process.
    • The player commands the first guy to pee out a window to get the attention of a guy with a ladder. He decides not to, but ends up doing it later anyway... just as the second guy had a change of heart, causing him to fall over and break the ladder.
    • The broken ladder is revealed to not need any cementing to hold it together after the second guy decides to make some out of pee and dirt. Even then, his attempts to climb it are thwarted by some badly-timed projectile vomit.
    • The first guy is saved from a flooding room by the second guy turning off the switch blocking him off from the exit. He's hoisted up by the second guy, then somehow knocks himself into a nearby lever and breaks it while the second guy tumbles into the room below. The bars blocking the exit are now replaced with spikes.
  • Fire-Forged Friends: Although the circumstances are definitely sketchy, the first and second prisoners eventually consider each other buddies through their adventure. So much so, in fact, that when one of them dies from blood loss, the other is so grief-struck he kills himself then and there.
  • Flipping the Bird: Both the first and second guys greet each other this way after gaining their pumpkin armor.
  • Foreshadowing:
    • The first guy is commanded to hollow out the pumpkin in his cell and use it as a helmet in case the ceiling caves in from the third guy's drill. He never ends up doing it, but the second guy eventually makes one he uses for the rest of the comic after he gets a pumpkin stuck on his head while cleaning up the first guy's mess.
    • The second guy decides not to use his gun in case he needs the bullets to off himself later. He eventually does so at the very end of the first route.
  • Forgot About His Powers: Despite the prisoners owning a trusty spoon, trusty knives, and a drill, neither of them think to use their tools for anything other than the event these items are introduced in. A couple of dead prisoners even had a pistol, but only ended up killing each other with their bare hands.
  • Genre Shift: Hitting the Reset Button apparently changed the genre with it, as the plot goes from an unconventional Great Escape to Urban Fantasy.
  • Giant Food: The second guy's pumpkin helmet becomes big enough to ride in thanks to a Pumpkin Hugeifier on the roof.
  • Gorn: Lovingly rendered in pixely monochrome, and incredibly messy at its best. For example, the attempt to use a prison guard as battering ram or the usage of intestines as rope.
  • Gory Discretion Shot: The second prisoner shooting himself in the head after crossing the Despair Event Horizon is only seen from the shadow he makes on a nearby stump. This is the only death in the comic that's given this treatment, with all other ones showing the process in full detail.
  • Hooking the Keys: A number of variants for this Adventure Game-style comic about breaking out of jail:
    • One of the guys already has a key, but it doesn't work on his door, so he attempts to use a broken ladder to give it to one of the other prisoners who has a window into his cell. It doesn't exactly work...
    • One of the other prisoners attempts to use the unconscious prison guard's belt to thread through the window of his cell to retrieve the keys that are lying on the floor outside. This also fails, and he just drops the belt.
  • Improvised Armour: The main two prisoners make a suit of pumpkins and a pumpkin helmet respectively.
  • Informing the Fourth Wall: Parodied when Hussie doesn't feel like illustrating an answer. This is usually accompanied by a close-up of the commanded character with Confused Question Marks over their head.
    "I'm sorry, I don't think I can do that with all future input from betelgeuse."
  • Interactive Comic
  • Inventional Wisdom: The second guy manages to build a robot out of broken ladder parts and dubs him Logorg. This would easily have been his greatest feat... if he remembered to put moving parts in it.
  • Kill 'Em All: All the introduced characters in the first route, up to and including the first prisoner, wind up dead by the end.
  • Magick: More like Majyyks.
  • Meaningful Rename: After being rebuilt with a new drill arm, Logorg is renamed Drillgorg by its creator.
  • Leaning on the Fourth Wall: After a particularly frustrating series of commands that ends in knocking out a guard and scattering his keys out of reach:
    > Ask dungeon master if there is one fucking way out of room
    He's unconscious!
  • Lighter and Softer: Compared to the first route, the second is completely bloodless.
  • Lock and Key Puzzle: One room has a fairly simple one, where there are three pumpkin-shaped holes in the wall with different expressions. Having just come out of a room filled with pumpkins and a transporter, the main guy decides this doesn't mean anything, carves a random face out of the one innociously sitting in front of him, and shoves it in the wrong hole. Predictably, the room floods.
  • Make a Wish: In the second route, the main character summons an elf that can offer wishes in exchange for babies. He promises two, then wishes for a pony and to get out of jail.
  • Major Injury Underreaction: The main character gets a harpoon in his stomach and manages to get all the way out to the woods and near the suicide stump before finally dying of blood loss. He is perfectly cognizant of his actions and is even able to move about and do quite a number of things without behaving as though he is in pain.
  • Minimalist Cast: There's only 10 characters in the story, major or otherwise (the 3 prisoners, the 3 children, the 2 elves, the guard, and the pony). While this makes sense considering it's a smaller story, it can be a bit jarring compared to Problem Sleuth's and especially Homestuck's Loads and Loads of Characters.
  • Nameless Narrative: Just about all of the main characters lack names. The MSPA wiki even refers to the three before the reset as "The First Guy", "The Other Guy" (the one who built Logorg), and "The Drill Guy".
  • No Ending: The elves try to make the pony kill the prisoner and the children he kidnapped but instead it just climbs into their bed and falls alseep. The end.
  • Noodle Implements:
    • The jail cell with the prisoner skeletons in it implies they got into antics with a violin, a gun, and a boot (which was on one of the skeletons' head).
    • Directly above this scene was a rope leading to the top of the prison complex, which turns out to be the small intestine of a harpooned sperm whale on the roof.
  • Only Six Faces: Only one face, actually. There is very little to tell the characters apart, which might be part of the reason why they make their pumpkin armor later on in the story.
  • Painting the Medium: Like the comic it was based on, the fan soundtrack refuses to acknowledge its own existence despite clearly being visible by not allowing listeners to purchase the tracks. Except for three tracks, but they cost $999.99, $717.17, and $413 respectively anyway to discourage purchase.
    > Purchase entire album and see what happens.
    The album can't exist!
    > Wait, what?
    You ass, Jailbreak never had a soundtrack! You're messing with the balance of reality itself, here.
  • Pyrrhic Victory: The first and second prisoners finally make it out of jail and into a secluded forest, but the first guy dies of his injuries (that the second guy unwittingly caused) before they can run off together.
    This is no victory. The feeling is vast emptiness. You are no longer bound by bars or concrete, but you feel more incarcerated than ever. You come to the heartwrenching conclusion that the only true prison... is loneliness.
    There is only one thing left to do.
  • Rain of Blood: When the guy with the drill dies, the blood from his snapped neck drains through the hole he drilled on the first guy's ceiling.
  • Random Events Plot
  • Reset Button: Gets pressed here after an abruptly depressing end.
  • Rule of Funny: Undeniably its sole motivation.
  • Running Gag:
    • Pumpkins, which may or may not be actually there.
    • In the earlier pages, the second guy having his ladder broken.
  • Schrödinger's Gun: The tree stump in the forest is retroactively linked to a scenario where the player can possibly kill themself, provided they're miserable enough and have a gun on them. In the first route, one of the players brings a gun found earlier to the area and does the deed, having gone through sufficient enough trauma. In the second, a gun is already there; since the scenario just started, the gun is instead unloaded.
  • Shared Universe: The story of Jailbreak is revealed to take place in the Problem Sleuth universe durring the latter's plot, which incidentally explains some of the aspects of what happened in the story.
  • Shout-Out to Shakespeare: Attempted by the first prisoner, but sadly he doesn't know any lines.
  • Skewed Priorities: In the second route, the first guy is given the chance by an elf to wish for something. He wishes for a pony, then wishes himself out of jail after bargaining with the elf for a second wish.
  • This Is a Drill: The guy above the main character had a drill in his cell. Drillgorg is later rebuilt with it in place of one hand.
  • Toilet Humor: Primarily in the earlier commands, which involved a lot of peeing and one instance of taking a dump.
  • Voodoo Shark: The pumpkins appearing/disappearing were eventually shown to be the work of a Pumpkin Appearifier in the next building. Why such a room would be needed is never explained.
  • Would Hurt a Child: Played with. The main character takes three children hostages in order to get the elves to let him inside their bungalow, but he is knowingly threatening them with an unloaded gun. The elves, on the other hand, eat human babies and were perfectly willing to make the pony trample the kids along with the prisoner.
  • You Can't Get Ye Flask: What pumpkin? Except of course, when there is one, and you were obviously too ignorant to notice.
  • You Wake Up in a Room: A textbook example.

> With your trusty spoon, dig deeper for more info.

> Check prison register.
> Look at subjective tropes.
> Show off your obscure factoid smarts.
> What are we doing again?

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9/24/2006 - 9/06/2011note 
??? days
134 pages
449 panels
4875 words (incl. 168 transcribed)
1 Pumpkin destroyed
3 Urinations
1 Decapitation
1 Harpooning
2 Elves summoned
1 Pony
Anthony Bailey, stats for Jailbreak

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