Get Into Jail Free

John Doe needs to get information from (or kill) Richard Roe. Unfortunately, Richard Roe has just been thrown into prison. How to get access to someone surrounded by high walls, barbed wire and armed guards? Why, commit a crime and get imprisoned yourself! After all, escaping should be easy for our hero once the deed is done!

Undercover police officers do this in real life, but in fiction they go one step further and actually commit a crime instead of just faking a criminal record. Of course, John Doe may not have the luxury of law enforcement co-operation. However, this raises the question of how he'd arrange to be thrown into the same prison or cellblock as the inmate he needs to approach.

Supertrope to Can't Get in Trouble For Nuthin'. See also Trojan Prisoner, Play-Along Prisoner, Conveniently Cellmates and Chained Heat.

Examples of Get Into Jail Free include:

Anime and Manga

Near the end of Outlaw Star, Gene arranges himself to be sent to an outer-space Alcatraz in order to get the information that an inmate has regarding the MacGuffin.
This happens in one episode of Golgo 13. Duke Togo allows himself to be arrested so he'll end up in the same ludicrously high-security prison as his target, a crook whose old companions are worried about spilling the beans on them. Needless to say, escaping a prison that makes The Alcatraz look like a cardboard box is no problem for Golgo 13!

Comic Books

In Suicide Squad #6, Harley Quinn shoots up a police car outside of a police station in order to get herself arrested and taken inside the station where the Joker's skinned face is being kept.
Batman villain Black Mask's accomplice, Circe, tries to get Harvey "Two-Face" Dent to do this - return to Arkham Asylum and kill Black Mask while he's in there.

Film

Fear is the Key (1972), a film adaptation of the novel by Alistair MacLean. The protagonist gets into a bar brawl with the police so he can get hauled into a courtroom where he takes the daughter of a millionaire hostage and a Car Chase ensues. The entire event turns out to have been faked by the police to give the protagonist a convincing criminal background, as the girl's father is involved with The Mafia. In the novel though the bar brawl at least is implied never to have happened.
In Let's Go to Prison, the protagonist is a convicted criminal with a plan for revenge on the judge that locked him up over and over since he was a preteen. Unfortunately, he gets his plan together a day late and the judge is already dead from natural causes. Instead, he goes after the deadbeat son of the dearly departed judge and gets the guy busted for drugs, then he deliberately gets himself arrested so he can become the deadbeat's cellmate for the sole purpose of making his life hell (he pleads guilty on condition of being allowed to serve his sentence at that specific prison). Eventually, the two are forced to bond together in order to make it through their prison stay alive.
In the Otto Preminger LSD comedy Skidoo, a retired hit man (Jackie Gleason) is ordered by The Don (Groucho Marx, in his last role) to get himself into prison to kill a snitch (Mickey Rooney).
The Joker does this in The Dark Knight in order to kidnap Lau to make him reveal where the mobsters' money is.
This is the premise in Face Off
|Mission Impossible: Ghost Protocol starts out with the team breaking Ethan Hunt out of a Norwegian prison. In the end, it turns out that he was actually there because he got arrested in order to infiltrate the prison and gather information from Bogdan.

Literature

In one of the books of the CHERUB Series, Teen Superspy James Adam's assignment is to go undercover in an Arizonan maximum security juvenile prison and engineer the escape of himself and one of the juvenile inmates. The plan is that the inmate he is helping them escape will lead them to his fugitive mother, a wanted international black market arms dealer. He does this by posing as a juvenile with a felony record, which is faked by the FBI.
In Savannah Swingsaw Mack Bolan discovers an elite KGB assassin is after a petty embezzler, so he gets thrown into prison. Hal Brognola creates a fake criminal record, but Bolan commits a burglary so he'll be caught by local police, in order to get close to the kid, avert the plot and find out why he's being targeted. Things go pear-shaped though when some fellow vigilantes recognise Bolan and bust him out, thinking they're doing him a favour.
The Stainless Steel Rat does this at both ends of his career:
- In A Stainless Steel Rat Is Born, a young DiGriz allows himself to get caught in the belief that he'll meet criminal masterminds in prison who'll teach him the art of crime. As it turns out, he only meets the pathetic losers who are dumb enough to be caught.
- He does have to try to get into an actual prison rather than juvenile hall. When the judge is about to give him a reduced sentence, he flips out in court and attacks a reporter, causing the judge to lose all sympathy.
- The Distant Finale of the series is a short story where the Rat, as an old man, apparently loses his touch and gets arrested and imprisoned. It turns out he's still got it, and let himself get caught as the first step of a plan to bust an old friend out of the prison.
In his final novel, Quiller discovers a witness who has evidence that can bring down a high-ranking boss of The Mafiya has been thrown into The Gulag. He gets himself sent there too (though only by faking the conviction papers) even through no-one has ever escaped before.
Happens in Warbreaker when Vasher gets arrested in order to get Breath from a captured rebel.

Live Action TV

The entire premise of Prison Break. A man is Wrongly Accused and his brother, Michael Scofield, commits a bank robbery so he'll be caught and thrown into the same prison (Scofield pleads 'no contest' on condition he's sent to a prison near his home) to help him escape. It helps that Scofield designed the prison, and the design is now tattooed onto his body.
The Sarah Connor Chronicles. Vick finds one of his targets has been thrown into jail, so he follows suit by the simple method of walking up to a group of police officers and punching one of them. Of course being a Terminator he can get out at any time just by knocking the cell door off its hinges. Notably, this one manages to get around the big issue of being sent to the same area as the prisoner in question, because the target is in temporary holding, just like Vick would be when assaulting a cop. Once he's inside, he can literally just rip the doors off the walls until he finds his target.
In Burn Notice, Michael askes to be put in prison for a week to protect a friend of Sam. This ends with a prison riot, and the man who wants Sam's friend dead being broken out of prison, and set up to go right back. Mike manages to get in by use of the two FBI agents who owe him a favor from a previous episode.
In an episode of Due South, a key witness is behind bars and Fraser's partner is jailed for contempt. Fraser gets himself arrested to join them and be in position to protect them. He's such a straight arrow that he can't bring himself to shoplift a candy bar, and his police friends have to plant it on him.
- In another episode, he gets himself interred in a mental hospital (to help break Ray out) by showing up in his RCMP uniform and telling them the unaltered truth of how he ended up in Chicago.
Chris Ryans Strike Back. John Porter gets arrested in Zimbabwe for dealing in illicit diamonds so he'll be thrown into a high-security prison where a British national is accused of trying to kill Robert Mugabe. Porter's job is to break the Brit out, interrogate and then kill him.
Done in the |Mission Impossible episode "Old Man Out". Of course, the IMF stacks the deck in their favour to get the result they want. Rollin is arrested for pickpocketing right outside the prison, and the arresting officer is Dan Briggs disguised as someone high-ranked enough to order the prison to hold him till he can be charged.
One episode of Batman had The Penguin try this after acquiring samples of various rich people's handwriting, because a forger has been imprisoned next to his usual cell.
In Veronica Mars, Logan takes a tire iron to a police car in order to get thrown into a holding cell...with the guys who nearly raped Veronica. We get a nice Oh Crap look from them, and the scene ends.
In Supernatural the Winchester's get deliberately caught so they can remove a ghost haunting the prison. The warden was the one who called them in, which helped.
In Justified Boyd Crowder assaults a US Marshal in a federal courthouse in front of dozens of witnesses. He assaulted a federal agent on federal property specifically so he would be sent to the federal prison rather than county jail. Once inside he bribes a crooked guard to be placed in the right cell. He is trying to get close to Dickie Bennett who is in the prison awaiting trial on federal charges. Raylan figures this out and tried to thwart the plan by having the charges dropped and Boyd released.
The Practice: To avenge a deceased relative, a man kills the hitman and arranges to serve his sentence at the very same prison the one who hired the hitman was serving time for another crime.

Video Games

A sidequest in The Elder Scrolls IV: Oblivion involves getting yourself imprisoned to gain the trust of an inmate, who you are told has hidden a stash of treasure somewhere.
At one point in Baldur's Gate II you have to get yourself sent to Spellhold - which is actually the local asylum, but it plays out similarly. The easiest way to do so is to tell the local Lord you must be deranged because you travel with Minsc. After being subjected to Minsc's conversation for a few minutes he wholeheartedly agrees and sends you there forthwith.
This is how you get to join the terrorists in Splinter Cell: Double Agent
The Opening of Batman: Arkham City
Excelsior Phase One: Lysandia: The PC must speak to a political prisoner, and so when the guards mention they're looking for a murderer and ask if the player knows who he is, the PC turns himself in.
Grand Theft Auto 2 features a mission where the Rednecks want the protagonist to shoot up Alma Mater Prison from the inside. The player has to get arrested while selling moonshine to get in.

Western Animation

In Avatar: The Last Airbender, Katara gets herself arrested for (bogus) Earthbending so she can find the Fire Nation's Earthbender-proof prison and free the prisoners.
In the Mega Man cartoon, Megaman decided the best way to get to Dr. Light and Roll in the Wily-run future was to get himself arrested, so he hit a copbot over the head with a lamppost. It worked.
In Jackie Chan Adventures, Jackie is guised up as a criminal to get into jail to find a MacGuffin. He did this to stop the bad guys Got Into Jail Free for the same reason.
In one episode of Darkwing Duck, Darkwing pretends to be a supervillain so he can get thrown into supervillain prison. Getting arrested turns out to be ludicrously difficult, however.