Jail Bake

I "saw" you might be hungry.

"So, apparently, there was something in that cake, and he used it to escape. And then I got fired. Pretty lame, huh?"

— Dave Panpa, Henry Stickmin: Stealing the Diamond

The stereotypical way to smuggle escape tools into a prison is by hiding them in a cake and giving them to the prisoner. Usually, a file is the item hidden inside, although files can't actually cut through iron bars in real life.

A common parody is for the nature of the cake to be plainly obvious, such as having the file (or something even larger, like a saw) visibly sticking out of the cake which the guards naturally fail to notice. Other variations include: the prisoner digging through a cake he received expecting to find a file inside, only to be disappointed when it turns out to just be a regular cake given in an attempt to cheer them up (by someone who is most likely extremely hurt after watching the prisoner destroy their nice gift right in front of them); as well as the complete opposite scenario, where the prisoner assumes it is a regular cake and eats the whole thing only to be informed afterwards that there was a file inside (or a key).

Fun random fact: In French the word for a file and a lime (the citrus) are the same (Lime) so it's a common joke to have a character ask for a file only to receive a lime instead.

Not to be confused with Jailbait, which may facilitate the need for a Jail Bake if you're not careful.

May be a part of a Prisoner's Last Meal.

Compare Pet Gets the Keys, for another way of getting implements of escape to prisoners, and Bedsheet Ladder, another stereotypical part of a Great Escape. See also Sickbed Smuggling (though it relates to smuggling a forbidden gift into a hospitalized person instead of helping anyone escape). For examples out of prison intended to actually hurt unsuspecting people, see Razor Apples.

---

Examples:

Advertising

• 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.

Comic Books

• Subverted with one Archie Comics alternate-universe story which puts the gang in a Conan the Barbarian-type setting—Archie, Jughead, and Reggie have been imprisoned and are set to be executed at dawn, so Betty and Veronica attempt to sneak a cake to them, ostensibly as their last meal, with the intention that the boys will use the iron cutter hidden inside the cake to cut their way to freedom. Unfortunately, Betty forgot to put the iron cutter in the cake...but that becomes a moot point when the boys turn up free anyway, with the explanation that the cake was hard enough for them to use it to beat the guard senseless.
• 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.
• Batman: 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 a 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.
• Bigfoot Bill: When Bill is put in a cell, Chupa gives him a taco and has to point out the nail file that's inside. Bill's not sure what to do with it.
• In Chevalier, a Lady brings some bread for the imprisoned heroes, which the suspicious guard breaks but finds no file inside. Claiming to be insulted, she tells the guard to bring the prisoners this musical instrument as an apology (one of them is a bard). The Lady had put the file in the instrument, using the bread as decoy.
• Disney Ducks Comic Universe: 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.
• Attempted in Doctor Who Magazine when the Doctor is the victim of a The Corpse Stops Here situation. But the prison has a scanner that detects the Sonic in the cake, so Izzy ends up being sentenced to “twelve months for attempted relocation of a felon”.
• Often happens in Lucky Luke.
  • In one story it is even inverted: The file in the cake is such a low quality that it is cut through by the bars it is attempting to file, but when Averell — resident Big Eater extraordinaire — says that "mom's cooking hasn't improved either." It dawns on his brothers that the cake is so rock-hard, it can be used 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 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".
• 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.

Comic Strips

• Subverted in Madam & Eve when the Andersons are sent to prison. Eve sends them a cake with two files inside, and the elated ladies immediately use them... to work on their manicures.◊
• 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."
• 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 has the prisoner facepalming when he receives a filing cabinet with a cake inside.

Films — Live-Action

• Subverted in Ariel (1988). 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.
• The first Fantozzi movie has a strange example in which the prisoner tricks the wardens into this: Fantozzi had entered a slimming hospital only to be locked in a cell with no food during the day and the personnel selling ridiculously overpriced food by night, even having pre-made promissory notes for the patients that have ran out of cash, and Fantozzi, after a few days, orders a portion of Montecristo spaghetti (paid with invalid notes, as he gave the wrong data), pulls out a file from it, and uses it to escape.
• In The Grand Budapest Hotel, Zero's girlfriend Agatha, who works for renowned baker Mendl's, 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 exquisite Mendl's pastries. For further parody points, said rock hammers and chisels are the size of a thimble but used anyway.
• In The Stinger of Hobbs & Shaw, Deckard and Hattie are visiting their mother in prison. Deckard passes his mother a cake, but then says "I wouldn't eat it" indicating it's a tool to break her out. Mrs. Shaw then smiles and says, "Let's get out of here".
• Lost in a Harem: In order to help Hazel, Peter and Harvey escape their cell early on, Prince Ramo smuggles a saw and other tools into the jail in a loaf of bread... though it doesn't work out like intended, because a guard hears the commotion and ends up opening the door and entering the cell, allowing the boys to trigger the derelict's Berserk Button and escape while he's attacking the guard.
• Marvel Cinematic Universe:
  • 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.
  • In Black Widow (2021), Natasha sends a package to Alexei, using baked sweets as distraction for the guards while an earpiece is hidden inside of a Red Guardian figure, which allows Alexei to know how he'll break out of prison.
• 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.
• 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.
• The wuxia Ode to Gallantry has an important MacGuffin, a metal plate, being baked into a pancake. It ultimately ends up in the hands of the Idiot Hero early in the film, kicking off the rest of the plot.
• Pee-wee's Big Adventure. When the film chronicling Pee-wee's journey is playing at the end, the criminal named Mickey who Pee-wee had met is invited to the premiere, but he's being kept under police supervision. Pee-wee tries none-too-subtly to sneak Mickey a file by putting it in his foot-long hot dog; the policeman confiscates it.
• Rancho Notorious: The crooked sheriff of Gunsight attempts to smuggle a lockpick to his cronies in jail by hiding it inside a bottle of whisky. Due to a mix-up, the bottle winds up in Vern's hands instead.
• In Buster Keaton's Steamboat Bill, Jr.. the title character attempts to smuggle tools to his jailed father in a loaf of bread.
• In Superbad, Seth rambles to Evan that this trope won't help break Fogell out of jail.
• Discussed in Take the Money and Run. When Virgil's wife comes to visit him in prison, he asks her to bake him a chocolate cake with a gun inside it, along with a batch of chocolate chip cookies with each one containing a bullet, but his wife is hesitant to do this because Virgil is allergic to chocolate.
• In the South Korean blockbuster A Taxi Driver, Kim and Peter smuggle footage of the Gwangju massacre into cookie boxes so that Peter won't run into any trouble at the Gimpo Airport when he flies back to Japan.

Jokes

• 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.

Literature

• 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 20 Years After to free the Duke of Beaufort. After receiving the bake, 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."
• 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 believes 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.
• 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.
• 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.
• The Louis L'Amour short story “The Sixth Shotgun” plays with this, while suggesting that just one file isn’t enough to saw through bars but that multiple files can do the job. A Soiled Dove who is sweet on an outlaw Wrongfully Accused of murder tries to give him a cake with four nail files hidden inside. The sheriff quickly sees through this ruse and points out that he can arrest her for attempted jail break if he wants to. He starts questioning her about what happened to two more nail files she bought with the other four but is interrupted when the judge’s daughter (who is also in love with the prisoner) comes in asking to give the prisoner his guitar to help him pass the time. The sheriff unwisely allows this without inspecting the guitar. On the day the hanging is scheduled for, he finds his prisoner’s cell empty except for a mocking note.
• Used for a Kick the Dog in Sounder; the guard smashes a birthday cake under the pretext of searching it over this trope.
• The Syrena Legacy: In Of Triton, Galen and Grom give Nalia, who is being held prisoner in the Ice Caverns, a codfish that has a lionfish spike hidden inside.
• 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...

Live-Action TV

• 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.
• Arrow. An Enemy Civil War within the League of Assassins is started by Mesi Natifah bringing a captive Nyssa al-Ghul a pepper with a small knife hidden inside—all she needs to cut the guard's throat and take his sword.
  Natifah: The pepper came from the garden. The garden grows strong even in your absence. Please try a bite.
• Batman (1966): 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.
• Bewitched has a case where the cake was magically conjured by accident.
• Big Brother: Played straight in a UK series, with a prison task, in which half the housemates were prisoners, and the other half prison officers. A cake with "Shhhhh!" iced on it was delivered to the prisoners, containing instructions to find a secret passage to a luxury spa. The prisoners had to time their use of this carefully, because at certain times, they would be on CCTV to the prison officers.
• 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.
• 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.
• 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 excitement 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.
• 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.
• Escape at Dannemora: Tilly smuggles hacksaw blades into prison by putting them in a container of ground beef and asking a guard to deliver it for her.
• 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.
• 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.
  99: What?
  Max: What if somebody thought of baking a file into a cake? Why, it could disrupt our whole prison system!
• 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.
• 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!
• 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.
• In Kenan & Kel, Kel tries to get Kenan out of prison with a VERY obvious saw in a cake. It's also a classic wood saw, whereas the prison is concrete and metal.
• 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*
• Law & Order: SVU: Chekhov's Gunman Bronwyn Freed uses this method to assist William Lewis to escape from jail, and then does the same for Dr. Rudnick (which turns into an even bigger mess when Dr. Yates invites himself along for the ride). Despite being Bound and Gagged and left in a car trunk in the latter case, she's still convinced she was right.
• 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.
• At the start of the second season of Mission Top Secret, the security of the prison Big Bad Neville Savage is about to escape is demonstrated by having the guards screen all incoming mail with an X-ray machine. The lead guard then triumphantly pulls a file out of a cake.
• 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.
• Used for a gag gift in Mom, at Regina's going-away party before she goes to prison Christy gives her a cupcake with a large file stuck through the middle.
• On My Name Is Earl, during Joy's trial, Darnell gave lemon squares to her lawyer and the lawyer's interpreter. The interpreter cut his tongue on a razor blade. Darnell had baked another batch of lemon squares as a thank-you gift, and that batch with the razor blade was for Joy...he got them mixed up.
• 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 Psych, after Gus accidentally tampers with a crime scene, Shawn promises to bring him a cake with a gun in it.
• 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.
• Subverted in the Star Trek: Deep Space Nine episode "Sacrifice of Angels" when a very nervous Quark shows up with a hasperat soufflé to give to a group of prisoners that includes his brother Rom. The guard (and probably the audience) assumes it's this trope, but it's actually a decoy; while he's distracted inspecting the soufflé for contraband, Ziyal sneaks up behind him and hits him with an Instant Sedation hypospray, causing him to pass out face-first in the soufflé.
  Quark: Now you've ruined it.
• In Watchmen (2019), due to a bug in his mental programming or whatever, Phillips keeps offering Veidt a horseshoe with his cake. In Episode 8, Veidt notices the horseshoe has been baked into his annual cake and gleefully uses it to start digging himself out of his cell.
• In Zorro (1957), Diego de la Vega is once arrested by Sergeant García (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 García's appetite. The Sergeant just glares at Bernardo and lets him go, though.

Music

• 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 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."
• "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.
• Unintentionally done by the jailers themselves in Tom Waits' "Fish in the Jailhouse", where an inmate plans to pick the lock using fish bones scrounged from the prison cafeteria.
  Peoria Johnson told Dudlow Joe
  "I can break out of any old jail you know
  The bars are iron, the walls are stone
  All I need me is an old fish bone"
  They're serving fish in the jailhouse tonight
• "Quick Joey Small (Run Joey Run)"
  Sweet Mary Jane was going insane
  When she heard of Joey's jailbreak
  But she knew all the while 'cause she sent him a file
  Baked inside a fudge cake
• The Irish rebel folk song "My Old Man's a Provo":
  My daddy's up in Long Kesh now, to me it's just not right
  I'll say a special prayer for him when I go to bed tonight
  Today it was his birthday, I sent him in a cake
  There was Semtex in the candles, he'll be out before I wake!

Theatre

• In the original version of Carmen, the spoken dialogue in Act II reveals that after Don José was sent to prison for letting Carmen escape, Carmen sent him a bread roll containing a file so he could escape. José didn't use it, though, but served his sentence to retain his honor as a soldier, and later editions of the opera with sung recitatives instead of dialogue cut this detail altogether.

Video Games

• 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 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 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."
• Henry Stickmin Series: Escaping the Prison starts with the titular Henry Stickmin in prison receiving a cake with various items hidden in it; one of these is a file, but Henry can also use a phone, a drill, a teleporter, a NRG drink, or even a rocket launcher (note only three of the items will actually help Henry escape, the rest are the just the start of The Many Deaths of You). Also noteworthy is that Dave Panpa, one of the prison guards, was supposed to check the cake beforehand but clearly forgot to do so (and when he realizes he forgot when Rupert Price briefly mentions it to him, he tries to save face with bluster, not realizing there was something in the cake).^note The next game, Stealing the Diamond, shows that Dave got fired over the incident after Henry escaped (his mention of the events provides the page quote). The Omega Ending of Completing the Mission reveals that the package was sent by someone from the Center for Chaos Containment as part of a "multiverse defragmentation" operation.
• 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 Mother 3, Flint is locked up in prison after getting knocked out upon blindly attacking the villagers, so his son Claus sneaks him a nail file disguised in an apple.
• 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.
• Invoked in the name of the Saints Row 2 mission "File in the Cake". The Boss breaks an inmate out of prison, but does so by sneaking into the prison and destroying its power generator with a bomb, then storming the facility during the blackout rather than attempting a Jail Bake.
• One side mission in Scribblenauts Unlimited has you doing this to bust one of Maxwell's brothers out of prison.
• 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.
• 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.

Web Animation

• 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 the Cyanide and Happiness short Prison Pie combines this with Follow Your Nose when a prisoner is snuck in a good smelling pie to escape.

Web Comics

• Modest Medusa: When Jake and Charles are in jail together, the latter accused of killing the former, Modest pretends to be Jake's lawyer after playing Ace Attorney and gives him a store-bought swirly cake with a visible hole in it, hinting at its "special ingredient." Played for laughs as the police had already checked it and found it was just full of Pokémon cards. The pair use them to entertain themselves until they are released.
• Ziggy Pig and Silly Seal (2022): After Ziggy and Silly are sent to prison, Ziggy's mom sends him a cake with several files inside. Silly eats them.

Web Videos

• 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.

Western Animation

• Subverted in 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.
• In the Adventures of 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 Brick Block, to Mario and Luigi after Bowser throws them in the Bastille. The Block contains a Super Leaf that grants Raccoon Power to Mario, which he uses to break out of the Bastille.
• 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.
• 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.
• 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.
• Subverted in an episode of The Charlie Brown and Snoopy Show, where Snoopy and Woodstock ends up in a "Jack and the Beanstalk" story. Woodstock gets captured by the giant and put in a cage, so Snoopy goes and bakes a cake, putting a file inside. However, when he hands the cake to the Giant, he simply slams the cake to the cage, causing the file to fall to the floor in the process.
• Darkwing Duck:
  • Spoofed in an episode ("The Revenge of the Return of the Brainteasers, Too!"), 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.
• In the Dennis the Menace episode, "Gone to the Dogs", Dennis, Joey, and Ruff use a magical booth to travel to a dimension where dogs act like humans. While in this dimension, Ruff gains the abilities to stand upright and speak English. Unfortunately, the dogs in this dimension hate humans and have them imprisoned in pounds. When Dennis and Joey are imprisoned, Ruff disguises himself as an old lady and gives them a cake with a bone inside to saw their way out. Dennis asks Ruff why he couldn't have just brought a hacksaw instead, and Ruff tells him, "Never look a gift bone in the mouth!". Unfortunately, they all get caught by the guard and Ruff gets kicked out.
• In Disenchantment episode "You're the Bean", Trixy brings Elfo a cake that she claims contains something that will help him escape captivity. However, she meant mentally escape, as the thing in the cake is a nude drawing of her.
• Used by the Beagle Boys in DuckTales:
  • In 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.
  • 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 according to plan (Scrooge refuses to take the cake and Mrs. Beakley gets fed up, resulting in Scrooge accidentally pulling the grenade pin out of the cake and Mrs. Beakley having to throw it away as it blows up), 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.
• 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.
• The Fairly OddParents! episode "Anti-Poof" has Anti-Cosmo give his son Foop a cake with a file in it after the Anti-Fairy baby is locked up in a playpen-like cell at Abracatraz, which Foop then uses to trim his nails.
• 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.
• Used by Glo Worm in Glo Friends. He delivers a cake shaped like himself to the other glo friends he helped the Molegans capture before they leave for Glo Land. The cake contains a saw for them to escape while Glo Worm leads the Molegans into a trap.
• This trope is subverted in the Hanna-Barbera cartoon The Good, the Bad, and Huckleberry Hound, when three of the Dalton Brothers are in jail and the fourth is in a Paper-Thin Disguise as their grandmother who comes to bring them 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 just handed his brothers some shovels through the bars.
• 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.
• 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.
• On The Looney Tunes Show, Porky brings an incarcerated Daffy a cake. Daffy instantly tears it apart looking for a file, and screams at Porky for not putting one in... within the guard's earshot.
• At the end of The Loud House episode, "Rita Her Rights", Lisa walks into the jail center with a cake that obviously includes a file to try to break Rita out.
• The Mickey Mouse Works short "Big House Mickey" has Mickey ask Goofy to bring him a cake with a file in it 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 and take his keys. The guard then demonstrates and proceeds to do so to himself. Goofy however says he still doesn't understand the whole "knock out the guard" thing, so the guard has to use every other guard in jail as examples. As the guard then uses his own head again as example, Goofy grins to the audience holding the baton indicating Goofy was faking ignorance this whole time.
• In Ninjago, the ninja get arrested after Nadakahn frames them for various crimes. When Dareth (who's become their manager) comes to visit them, they ask him to get them out (presumably through legal means), and he tells them he baked tools into the cake he sent them. Most of them didn't even know they'd received a cake, because Cole ate it right away, tools and all (he was a ghost at the time, which is probably how he managed to digest them).
• In Olive, the Other Reindeer, Martini the penguin says that this was one of his jobs at the zoo.
• A rather funny variation occurs in the "Putt-Putt Pink" episode of The Pink Panther. At the end of the episode, the Pink Panther is caught by a cop who puts him in jail for all the problems he caused with his home-made motorbikes (which usually ended with the same cop on the receiving end of the Amusing Injuries). While in jail, The Pink Panther gets a cake decorated with a tiny motorbike on top that reads "For Pink Panther From Mother". The Pink Panther proceeds to ride the tiny motorbike to break the jail's metal door (squashing the cop in the process) and drives away.
• Rise of the Teenage Mutant Ninja Turtles: The "Tales of the Hidden City" arc ends with Mikey and Splinter breaking everyone out of prison by sneaking Leo's odachi inside a giant cake under the guise of being their lawyers.
• In the Sandokan – The Tiger of Malaysia, Sandokan and crew have been arrested by a local noble who sentences them to death, but nonetheless has his personal cook prepare a sumptuous Last Meal for them, including a huge cake. Sandokan's still-free ally visits the cook, and once the latter's back is turned, discreetly inserts a pair of files and a message in the cake.
• South Park:
  • In the episode "Cartman's Silly Hate Crime", the boys visit an imprisoned Cartman with a cake with a file in it so he can bust out and participate in their sled race. Cartman is too dumb to understand Kyle explaining the plan to him in Pig Latin but it's moot anyway because it turns out he's not allowed to bring food back to his cell, most likely because of situations like this. This trope is lampshaded by Stan, who claims to have seen it happen in a movie.
  • In "Credigree Weed St. Patrick's Day Special", the boys sneak Randy's weed to him in jail by baking it into a St. Patrick's Day cake. At first, he doesn't realize it and lashes out at Stan until he finally gets the hint.
• In the SpongeBob SquarePants episode "Jailbreak", Karen visits Plankton in jail and brings him a cake, and he quietly asks her if she put a file in the cake. She just laughs it off, asking who would put a file in a cake. Later, Plankton gets eaten by another prisoner who has a slice of cake and a file in his stomach.
• 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 an allergic reaction in Sheriff because he's allergic to gluten.
• 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.
• The T.U.F.F. Puppy episode "Tattle Tale" had a variant where, rather than prison, Dudley and Kitty were sent to T.U.F.F. Detention after F.L.O.P.P. tattled on them for sleeping on the job (in Kitty's case, she was actually knocked unconscious from being forced to lug around a heavy piano by the Chief). When Dudley and Kitty are needed to stop F.L.O.P.P. from using an earthquake generator to destroy Petropolis, Keswick helps them escape the robot keeping them there by providing a cake that turns out to have a mallet inside. We're led to believe that Dudley will use the mallet to destroy the robot, but instead he injures himself and Kitty so that the robot will let them out of detention to see the nurse.
• In The Venture Brothers, Phantom Limb sends his regards to King Gorilla by baking a "Tarzan" into a cake.
• Wild West C.O.W.-Boys of Moo Mesa:
  • In the episode "A Snake in Cow's Clothing", smooth-talking conman Jacques LeBeef is framed and arrested by Mayor Bulloney and his lackeys. The ladies Jacques charmed throughout the episode show up at the jail with food for Jacques, but Sheriff Terri-Bull, no stranger to dirty tricks, checks each fruit basket first. He is more than a little annoyed to find tools hidden in each gift.
  • Discussed by Bat Blastagun's henchman Sid in "How the West was Shrunk" when Miss Lily tries to sneak in the shrunken C.O.W.-Boys by having them hide in one of her honeycakes. Sid warns Bat that there could be a file hidden in the cake.

Real Life

• A very early example of this is found in Zosimus' Historia Nova (5th century), which includes an incident in c.323 AD in which the wife of the Persian prince Hormisdas helped him escape by giving him a large cooked fish with a file hidden in its belly. While the guards were drunk with wine supplied by the wife, Hormisdas filed the shackles off his legs and made his getaway disguised as a eunuch.
• 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?
  • Mind, only the first few examples of baked goods needed to actually be bombs before the Nazis started treating every out-of-place cake and bread loaf as a potential bomb, allowing for La Résistance to cause a considerable amount of mayhem using regular flour.
    • Also, Nazi Germany and the countries it occupied were under strict rationing during the war (most of the food went to feed the army, and even they were short of supplies), with anyone not in the upper ranks of the government usually not able to get enough food. a cake delivered to a government office or gathering place of soldiers or workers would have been consumed even if they didn't know who delivered it. in most cases the OSS just arranged to have the baked goods labelled as a gift from some friendly organization, which was not a uncommon sight.
    • The more common use of the explosive 'flour' though was to have a baker turn it into scones, biscuits, or other such small dense baked goods, which the operative could carry around in public without attracting attention. A few biscuits in a pocket looks like a snack or a worker's lunch, not charges for sabotage. Combine with some chemical-fuse time detonators disguised as ink pens and you could walk around a city looking perfectly innocent while placing sabotage charges. They would also sometimes mix the explosive with coal dust and glue to create fake pieces of coal. Mixed into normal coal where it would explode when put into the firebox, it was an effective way to damage trains and older civilian ships.
• 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 60s. 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.

---