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- 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.
- Exploited in a Canadian Heritage Minute wherein political dissident Étienne Parent conceals his newspaper editorials in a pie plate, underneath the pie. While the British guard, clever or just awake to the absurdity of a prisoner sending baked goods out of jail, immediately looks under the pie and sticks his fingers in the filling, the courier slips the paper into his pocket.
- 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. In another, the wardens need a file, so they go through Tricky Jack's mail ("Why me?" "Your family is always sending you useful presents").
- Spoofed in a Scrooge McDuck story by 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.
- One Spy vs. Spy strip has the imprisoned spy receiving a cake which contains both a file and a picture of some sawed-through bars, leading to an unconscious guard-spy and resulting Fakeout Escape.
- The Penguin pulls this trick in Detective Comics #59 when he delivers a cake to his accomplice Bignose Mike in jail, complete with a Sarcastic Confession that the cake contains file. This makes the guard laugh so much that he doesn't bother searching it. Bignose Mike later uses the file hidden in the cake to escape.
- Spoofed in a Lupo Alberto story, where the main character was arrested due him looking like a fearsome criminal and the criminal's accomplices, not knowing their boss is still out, send him a cake hidden inside a file and a cake hidden inside a bigger cake, and were about to send him a file hidden inside a bigger file when their boss tracked them down. As the director puts it, the accomplices had "very good brains, like new. Never used. Two morons".
- 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 Superbad, Seth sarcastically suggests they use this trope to break Fogell out of jail.
- In Buster Keaton's Steamboat Bill, Jr.. the title character attempts to smuggle tools to his jailed father in a loaf of bread.
- In Iron Man 2, Justin Hammer sends Ivan Vanko a meat-and-mashed-potatoes dinner...except the potatoes are actually plastic explosives, so Vanko can fake his death.
- Men in Black 3 has an alien symbiont (nicknamed "Weasel" in the Blu-ray disc commentary) creature smuggled inside a cake. A metal detector fails to catch it.
- In The Grand Budapest Hotel Zero's girlfriend hides rock hammers and chisels in the ornate pastries sent to Gustave in prison, not even bothering to disguise their shape. Even then, the guard who cuts up all the other food sent to inmates can't bring himself to destroy them.
- Subverted in Ariel. Kasurinen gets a cake and a book on his "birthday". The cake is thoroughly examined by the prison guard. The file is between the pages of the book.
- 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. Causes a Crowning Moment Of Funny when the Duke invites his warden to dinner, describes 'hypothetically' what was in the bake and how he got it, produces the items for the break out and concludes with "Your guard actually works for me. I just found out too."
- 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...
- Used for a Kick the Dog in Sounder; the guard smashes a birthday cake under the pretext of searching it over this trope.
- Double Subverted and lampshaded in Bewary, Ride by Glenn Murrell. The Hero is framed for murder and in jail. The Love Interest wants to bring him a cake — just a cake, nothing special. But then her friend, who also beleives in the hero's innocence, visits her with an idea to smuggle a gun in there, noting that this trick is so old it might just work. She points that a six-shot wouldn't fit into the cake, but he pulls out a Derringer he got earlier from the hero as a gift. It works and the hero gets out using this literal Chekhov's Gun.
- In Pushing Daisies, Olive bakes a gun into a pie for Ned. For protection. The outline of the gun (and individual bullets) are clearly visible through the crust.
- 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, causing him to pass out face-first in the souffle.
Quark: Now you've ruined it.
- 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 The 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 for him. It basically has a plug-in Sawzall much larger than the torte itself on top of it. Crow thinks the illusion is nearly complete and that it just needs "a little more almond paste around the motor housing". Gypsy, however, is fooled.
- 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 & 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 smart 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 Chapulín 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.
- Reese is sent to a Beyond Scared Straight-like program in one episode of Malcolm in the Middle. When an inmate yells at him, he suggests that the inmate get someone to smuggle him some mouthwash in a cake because he has bad breath.
- On Gilligan's Island, Mr. Howell is in a jail cell (long story) and Mrs. Howell brings him a cake. Gilligan, the one who's guarding Mr. Howell, asks for a piece and just happens to take the piece with the file in it, leading Mrs. Howell to be arrested by Gilligan as well.
- On The Dukes of Hazzard, Bo, Luke, Roscoe and Boss Hogg are in jail. On visitors day, Lulu tries to smuggle tools to Boss hidden in a large sub sandwich.
- In Psych, after Gus accidentally tampers with a crime scene, Shawn promises to bring him a cake with a gun in it.
- In the Zorro TV series, Diego de la Vega is once arrested by Sergeant Garcia (because of a bad joke from an old friend of Diego). Bernardo tries bringing him a file inside a large sausage, but the subterfuge doesn't resist Garcia's appetite. The Sergeant just glares at Bernardo and lets him go, though.
- In a Dave Allen sketch, some jail prisoners receive a package that contains a cake, and assume it must contain something to help them escape. Their exitement ends quickly when they discover the cake is so hard, they can't even cut it. In frustration, one of them throws the cake at the wall - which collapses.
- One episode of Good Eats has B.A. ask his brother Alton for a cake with "a little something special inside", clearly expecting this trope. Alton, naturally, misses the point, thinking B.A. wants cream filling or the like.
- Get Smart: 99 bakes dentist tools that into a cake in the "The Whole Tooth and..." episode so Max can retrieve nuclear power plant plans hidden in the tooth cap of a prisoner.
Max: You baked dental instruments into the cake? That's a fantastic idea, 99. Where did you get it?
99: It's not so fantastic, Max. It's an old trick, really. People have been baking things into cakes for years.
Max: You know, a horrible thought just struck me, 99.
Max: What if somebody thought of baking a file into a cake? Why, it could disrupt our whole prison system!
- In an episode of Mork & Mindy, Mindy is jailed for not revealing her source for a story. Mork bakes her a cake shaped like a saw, containing a hacksaw blade.
- Law & Order: SVU: Chekhov's Gunman Bronwyn Freed uses this method to assist William Lewis and Dr. Yates and Dr. Rudnick to escape from jail. Despite being Bound and Gagged and left in a car trunk, she defends them.
- Referenced on The Golden Girls. Rose, Dorothy, and Blanche are mistaken for prostitutes and arrested, and a while later Sophia shows up.
Rose: Are you here to bail us out?Dorothy: No Rose, she's dropping off a manicotti with a file in it!
- 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 saw 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.
- "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). In one case it fails because he wears out the teeth of the saw by trying to cut the cake with it.
- Another newspaper comic had the prisoner facepalming when he receives a filing cabinet with a cake inside.
- A cartoon from the National Enquirer depicts a criminal and his wife standing in front of a playpen containing an unhappy-looking baby.
Wife: He said his first words today..."Bring me cupcake with file in it."
- 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: Clank can send weapons he finds to Ratchet in jail, the "cake" being nothing but a gun with icing and a few candles on top. Since Clank keeps sending him weapons, the Warden wonders just how many birthdays Ratchet has.
- in Escaping The Prison, the game starts with Henry in prison receiving a cake with an item hidden in it that can be a file, but can be a phone, a drill, a teleporter, a NRG drink, or even a rocket launcher instead. Also noteworthy is that one of the prison guards was supposed to check the cake beforehand but clearly forgot to do so.
- One side mission in Scribblenauts Unlimited has you doing this to bust one of Maxwell's brothers out of prison.
- 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."
- Subverted in a Team Fortress 2 comic focusing on Scout and Spy in Teufort's prison. The mayor delivers an apple pie with a file in it, but it's only a joke since the cell has six-inch thick Plexiglas instead of bars.
- In Awesomenauts, the icon for Vinnie and Spike's upgrade Chrome File (which increases the damage of Spike Dive) is a cake going through an x-ray machine with a file inside of it.
- In Lego City Undercover, Chase at one point encounters an old prison inmate named Blue who specializes in smuggling various items into the prison via giant cakes. He's even managed to get full-sized cars past security this way.
- In Bad Piggies, feeding the King Pig cakes causes him to belch out random points upgrades or power-ups, as well as some useless items, which include a file.
- 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. It ended up being unnecessary, since they were being held in a literal Cardboard Prison.
- In CollegeHumor's video "ShamWow Guy In Jail", Vince pitches various items to the other inmates. One of them is a cake slightly smaller than a football with a hacksaw hidden inside.
- 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 both Scrooge and Mrs. Beakley out.
- One particularly amusing variation has the cake itself be the tool. By now, the guards have gotten wise to the Beagles using the trope and have an X-Ray machine installed. Surprisingly, it contains nothing but actual cake. However, the cake gives Burger Beagle a case of the hiccups so bad his brothers are able to use him as a jackhammer to dig out.
- Another amusing example is from the Five-Episode Pilot when "El Capitan" sends them a package of explosives disguised as chocolates. Burger, being the Big Eater of the group, thinks they are chocolates, and eats one, with rather unpleasant results. And even when they realize what they are, he asks for another later. Fortunately, they keep him from eating any more, and use them to escape.
- 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 Bros., Phantom Limb sends his regards to King Gorilla by baking a "Tarzan" into a cake.
- This trope is subverted in the Hanna-Barbera cartoon The Good, the Bad and Huckleberry Hound, when one of the Dalton Brothers is in jail and another one of the Daltons in a Paper-Thin Disguise comes to bring him a cake. Huck is smart enough to expect this trope and carefully inspects the cake, but can't find anything suspicious about it. As it turns out, the cake was just a distraction, and while Huck was busy trying to find a file that wasn't there, the disguised Dalton went over to the imprisoned one and just handed him a file through the bars.
- Darkwing Duck:
- Spoofed in an episode, where a criminal on a literal Planet of Hats is given a file (they eat metal) 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 CatDog: A bunch of inmates 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. The cake was for the warden. But another package discreetly opened by his henchmen contained the Pan Ku Box used to open the demon gate.
- At the end of the Ed, Edd n Eddy episode "Eds-aggerate", Johnny gives the trio (who have been trapped in cement as retribution for a hoax they pulled) a cake with a hammer in it. Ed tries to eat the cake by himself, and the hammer gets stuck to the side of his face.
- 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 Super Mario Bros. Super Show, Toad (disguised as a French waiter aboard King Koopa's steamboat to try and rescue the Princess) not only baked a nail file into a cake, but a hacksaw, a power drill, and a brace as well.
- On The Looney Tunes Show, Porky brings an incarcerated 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 - In "Grime Doesn't Pay," jailbird Dishonest John gets a tool-filled birthday cake from his Mom - unfortunately for him, he guard who brings it forces DJ to eat the whole thing while he watches.
- Futurama: In "The Beast With A Billion Backs", when the Professor and Wernstrom are locked up, Leela smuggles them a cake which is actually the Professor's smellascope disguised as a cake.
- In an episode of Kung Fu Panda: Legends of Awesomeness, Taotie extorts his son, Bian Zao's help in escaping Chorh-Gom prison in exchange for some "father-son" time. Bian Zao and Po bake a whole series of cakes, and with each one, Bian Zao sneaks in pieces of the Iron Claws of Doom for Taotie to reconstruct. When Bian Zao stops himself from making the final delivery out of guilt, Po does it for him, unaware of Taotie's plan.
- Subverted in the The Adventures of Jimmy Neutron: Boy Genius episode "Who Framed Jimmy Neutron". Jimmy, in jail, tries to tell Sheen to bring him escape tools indirectly by telling Sheen to bring a book they read in class named "Drills, Hacksaws, and Shovels." Sheen shows up with a cake, and Carl pops out. When asked by Jimmy where the tools are, Sheen produces a book named "Book of Drills, Hacksaws, and Shovels." Carl and Sheen are then jailed with Jimmy for trying to break Jimmy out.
- Played with in the Bugs Bunny cartoon Big House Bunny. Prison guard Yosemite Sam is mistakenly locked inside a jail cell and Bugs, disguised as a crooked guard, hands him what appears to be a loaf of bread. It turns out to be a bread-shaped "Ajax Escape Kit", which zips open and contains digging tools and a map.
- This article over on the Smithsonian's blog details some real cases from the 19th and early 20th century on actual attempts to break inmates out of prison by sending them tools baked inside of cakes and pies.
- In an odd case of the cake itself being a tool, during World War II the OSS developed a type of plastique that could be disguised as cake. It was even edible. Particularly devious La Résistance operatives would bake the wiring into the bread and leave it on a target's doorstep, so that it would be set off when a metal knife cut into it. But really, why would you eat a found cake?
- One criminal who earned a nickname due to a trick like this was Connecticut resident Frederick Merrill, a violent career criminal with a record that dates back to the 60's. One of his many escapes from jail involved his mother smuggling a gun to him in a jar of homemade peanut butter, giving him the nickname "The Peanut Butter Bandit".
- The Acre Prison break involved the Irgun smuggling explosives into the prison. One of the people involved recounted a guard stabbing the top of a jam container all the way to the explosive layer and asking what was that on his blade. An inside man explained that sometimes jam gets lumpy, even tasting a bit of the substance as proof.
- The Iranian documentary This Is Not A Film was smuggled out of the country via a flash drive hidden inside a cake.
- In June 2015, a prison employee managed to pull this old trick on the maximum-security Clinton Correctional Facility in Dannemora, NY, by stuffing hacksaws and other tools into raw meat, freezing it, and getting it passed to two inmates by another (apparently unsuspecting) employee.