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The stereotypical way to smuggle escape tools into a prison is by hiding them in a cake and giving them to the prisoner. Most often a file is hidden in the cake.
A common parody is for the nature of the cake to be plainly obvious, such as having the file visibly sticking out of the cake or being simply a saw with frosting on top or for a prisoner to get disappointed that the cake is just a cake.
Not to be confused with Jail Bait, which may facilitate the need for a Jail Bake if you're not careful.
- Subverted in a commercial for painkillers: An elderly inmate's wife comes in for a visit with a basket full of goodies, one of which is a pie. She nods significantly at him and he nods back. Later, he opens the basket, rummages through the pie... and finds some painkillers, which he then uses to alleviate the pain of sawing through the bars with a file.
- In the Polish comic The Adventures of Ionek, Ionka and Blot, Blot is accused of this when he enters a prison disguised as an old lady. Subverted as the prisoner he was supposed to be visiting is just an excuse to get in.
- Often happens in Lucky Luke. In one story, it's the cake itself that's been baked so hard it serves as a file.
- Spoofed in a Scrooge McDuck story by Keno Don Rosa. The Beagle Boys visit their grandfather in prison, to celebrate the birthday of their gang. They bring a huge elaborate cake, of which not much was left after the security removed all sort of tools hidden inside. Including a flamethrower.
- ~Pee-Wee's Big Adventure~. Not in a cake, but in a footlong hot dog. Nice try, Pee-Wee.
- Lampshaded in The Naked Gun 33 1/3.
- Snow White and The Three Stooges used a sandwich.
- In the 2005 remake of The Longest Yard, Caretaker receives Megget's spikes (and implicitly all of the other items he procures for other inmates) in this manner.
- In Buster Keaton's Steamboat Bill Jr.. the title character attempts to smuggle tools to his jailed father in a loaf of bread.
- There's an old joke that goes:
Mom: I couldn't find that file you asked for, so I baked in some nail clippers and a pumice stone instead!
Prisoner: Thanks, Mom.
- In Nineteen Eighty-Four, Winston, after being imprisoned, thinks that the Brotherhood might send him a razor blade hidden in his food, not to escape but to kill himself with. It doesn't happen.
- Alexandre Dumas père uses it in Twenty Years After, the sequel to The Three Musketeers, to free the Duke of Beaufort.
- Mark Twain parodies this (and possibly other early uses) in Huckleberry Finn, where this is a part of Tom Sawyer's Rule of Cool plan to free Jim.
- Tom Holt inverts this in Falling Sideways: Someone hides a cake in a file. As in, a file folder. It was entirely for the sake of the pun.
- Discussed by Nanny Ogg in one of her postcards home in Witches Abroad:
Well here's a thing yore ole Mum doin Time in prison again, Im a old lag, youll have to send me a cake with a phial in it...
- In Pushing Daisies, Olive bakes a gun into a pie for Ned. For protection.
- Spoofed in Star Trek Deep Space Nine when a very nervous Quark shows up with a hasperat souffle to give to some prisoners; the guard digs around it as Quark squirms leading everyone to expect the discovery of a technobabble-esque file, but it's a distraction while someone else uses a hypospray on him.
- Spoofed in Fresno, when a guard inspected pudding for such things, and a woman just gave her husband tools directly while the guard wasn't looking.
- Bewitched has a case where the cake was magically conjured by accident.
- A Kids in The Hall skit made use of this trope, and adds dramatic tension with the guard asking if he can have a piece, while the prisoner sweats, hoping the guard's knife doesn't touch the saw. Of course the tension is then taken to ridiculous heights with the guard eating most of the cake without finding the saw, leaving an obvious saw-shaped piece of the middle of the cake. The guard looks full and is about to give the cake to the prisoner, but then he decides to have one more piece... * clink*
- In an episode of Mystery Science Theater 3000 where Mike is on trial for destroying several planets, Crow and Servo bake a torte with a nail file sticking out of it quite obviously. Gypsy, however, is fooled.
- The "file" was a plug-in Sawzall several times larger than the torte. Crow claimed "it just needs a bit more almond paste on the motor housing."
- In the Leverage episode "The Jailhouse Job", the team sends Nate a kielbasa with an earpiece hidden inside it. Another prisoner sees him tear apart the kielbasa and stick something into his ear and is suitably grossed out.
- The earpiece smuggled into prison was also used in The Lone Gunmen, but Yves smuggled Jimmy the earpiece in a bag of Cheetoes.
- In Kenan and Kel, Kel tries to get Kenan out of prison with a VERY obvious saw in a cake.
- The Commish: Tony (the eponymous Commish) has been jailed for Contempt of Court by a judge he suspects is on the take. He moves his office down to the cells and conducts business as usual. His wife comes by to check up on him and gives him a cake. She baked a file into it as a joke.
- One episode of The Adventures of Brisco County Jr had a lawyer use this to break her client out of jail, with a twist: The guards were Genre Savvy enough to destroy the cake to look for tools, then petty enough to eat it in front of the prisoner rather than give it to him. Then they discovered that the cake was drugged, allowing the lawyer to take the keys off the sleeping guards and let her client out.
- Batman: the Penguin's lackeys break him out of prison by baking a cake. The guard states that the police know about the metal file trick and the prison guards have orders to use a metal detector on all packages. The metal detector sets off an electromagnet that stuns the guard. The lackeys praise the Penguin's plan of using the regulations to his advantage.
- El Chapulin Colorado did it once with a woman placing a gun inside the cake for his husband on prison. A doctor comes later with an X-Ray machine and shows that the husband ate the whole cake, GUN INCLUDED.
- On an episode of Malcolm in the Middle, Reese and other kids become part of a "scared straight" program where they visit a jail and get yelled at by a prisoner. Reese snarkily suggests that he should have someone smuggle some mouthwash in a cake because he has bad breath.
- From Eminem's single "We Made You":
"Can you blame me? You're my Amy, I'm your Blake. Matter fact, make me a birthday cake with a sword blade in it to make my jailbreak."
- Referenced in the Johnny Cash song "I Got Stripes":
On a Monday my momma came to see me
On a Tuesday they caught me with a file
On a Wednesday I'm down in solitary
On a Thursday they said feed him bread and water for a while.
- From "I'll Be Hanged (If They're Gonna Hang Me):"
"So I wrote out to my sweetheart on the prairie,
I asked her if she'd help me make a break,
She sent a cake and put inside a hammer,
She forgot to send an axe to break the cake."
- A recurring gag in The Wizard of Id involves the Spook's mother attempting to send him a cake with a file in it (or, in one strip, a crosscut saw).
- Another newspaper comic had the prisoner facepalming when he receives a filing cabinet with a cake inside.
- Inverted in The Secret of Monkey Island. You need to get a file in order to steal a MacGuffin. It's in a piece of carrot cake a prisoner has. He gives it to you because he doesn't like carrot cake.
- In Mother 3, Flint is locked up in prison at one point, so his son Claus sneaks him a nail file disguised in...an apple. Close enough.
- Spoofed in Secret Agent Clank: The "cake" is nothing but a gun with a few candles on top.
- in the flash game Escaping The Prison, the prisoner starts by recieving a cake and the player can choose which items are inside it. A file is one of the options, but so are a teleporter and a rocket launcher.
- In Brink of Consciousness: Dorian Gray Syndrome, after you find a hacksaw inside a chocolate cake in the dining room of the villain's mansion, he comments over the loudspeaker system that it's "just like in jail."
- In the Homestar Runner cartoon Strong Bad is in Jail, Strong Mad baked a cake with a jackhammer in it for Strong Bad and The Cheat.
- Used by the Beagle Boys in DuckTales. Mrs. Beakly can't really pull it off, though.
- In Super DuckTales, when Scrooge gets arrested and thrown into jail, Mrs. Beakley smuggles in a grenade in a cake so that he can blow up the walls and get out. It...doesn't go to plan, and Huey, Dewey and Louie have to call on Gizmo Duck to break him out.
- One particularly amusing variation has the cake itself be the tool. It contains nothing but actual cake, but the cake gives one of the Beagle Boys a case of the hiccups so bad his brothers are able to use him as a jackhammer to dig out.
- A House of Mouse cartoon has Mickey ask Goofy to do this after Mickey is locked in jail. The guard notices; and he and Goofy end up having a long discussion on how this wouldn't really work and what tools should have been used, ending with the guard concluding that the easiest way to escape would be to knock him out. The guard then proceeds to do so to himself.
- In The Venture Brothers, Phantom Limb sends his regards to King Gorilla by baking a "Tarzan" into a cake. Squick.
- This trope is subverted in the Hanna-Barbera cartoon The Good, the Bad and Huckleberry Hound, when one of the Dalton Brothers (Stinky, I think) is in jail and Huck eats a cake Stinky received from one of the other Daltons in disguise. This was so Huck could check for a file, and there wasn't one. The reason it's a subversion is that it's obviously one of the other Daltons and you'd expect the cake to have a file, but then it doesn't (so far as I remember).
- That's because while he was busy eating the cake, the Dalton was handing jackhammers to his boys from out of his purse.
- Spoofed in an episode of Darkwing Duck, where a criminal on a literal Planet of Hats is given a file that has a cake inside, which he uses to incapacitate the guard.
- In another episode (Adopt-A-Con), Darkwing is thrown in Jail (Again), and Gos comes by with a cake..that has a chainsaw in it. It then keeps going, getting more random each time.
- Subverted in Cat Dog: A bunch of immates receive a file, but Shriek uses it on her fingernails and then uses said fingernails to pick the lock.
- In Olive the Other Reindeer, Martini the penguin says that this was one of his jobs at the zoo.
- Subverted in Jackie Chan Adventures. When Valmont and some of his henchmen intentionally get themselves locked up to get access to the inside of a prison to unlock a hidden demon gate, Valmont tore apart at a cake delivered to the prison hoping for some means of escape, only to get apprehended by guards for his behavior. But another package discreetly opened by his henchmen contained the Pan Ku Box used to open the demon gate.
- At the end of an episode of Ed, Edd 'n' Eddy, Johnny gives the trio (who have been trapped in cement as retribution for a hoax they pulled) a cake with a hammer in it.
- In the South Park episode "Cartman's Silly Hate Crime", the boys visit an imprisoned Cartman with a cake with a file in it. Turns out he's not allowed to bring food back to his cell.
- In the Galaxy Rangers episode "Changeling," Shane has to infiltrate a prison. Zach jokes that if he isn't out in the allotted time-frame, the rest of the team will send a hacksaw inside a cake.
- The Adventures of Super Mario Bros 3 episode "Super Koopa" has Toad bring a birthday cake, containing a "?" Block, to Mario and Luigi after Bowser throws them in the Bastille.
- On The Looney Tunes Show, Porky brings an encarcerated Daffy a cake. Daffy instantly tears it apart looking for the file, and screams at Porky for not putting one in... within earshot of the guard.
- Played with on an episode of Squidbillies where Rusty tries to break his grandpa out of prison with cake shaped like a hacksaw that reads "Prison is tough, hope you can hack it", turns out there's a gun baked into it. Turns out, the gun isn't used and instead the cake is stuffed in Sheriff's face and causes and allergic reaction in Sheriff because he's allergic to gluten.
- Beany and Cecil - jailbird Dishonest John gets a tool-filled birthday cake from Mom - unfortunately for him, the guard makes him eat it all up while he watches.