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Desires Prison Life

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Imprisonment is something that most people want to avoid. Between the constant surveillance, the cheap, low-grade food, the oftentimes violent fellow inmates, not seeing friends and loved ones, and being confined to a cell, prison is an unpleasant and undesirable destination.
But there are some people who find imprisonment more desirable than other available alternatives. Perhaps they're homeless vagrants, worn-out laborers, or other kinds of down-on-their-luck lumpenprolesnote Lumpenproletariat was Marx's term for the lowest class of people in impoverished areas, such as swindlers, petty thieves and prostitutes. He thought they would be reactionaries when the revolution came, and as such he thought they'd need to be "liquidated"., tired of being hungry and sleeping on the street. They might find the three hot meals a day in prison to be preferable to the insecurities of the "real world".
Other times, released convicts found a group of True Companions in prison, and desire to be reunited with their pals. Or maybe they managed to rise up in the prison hierarchy, gaining a position of respect running the Black Market, but outside the jail, they're discriminated against and seen as a lowly ex-con who's only good for the worst, lowest-paid jobs. Whatever the reasons, these characters are so eager to get back in jail that they'll commit crimes and let themselves get caught just to make that happen.
These prison-seeking people will almost never end up in a Luxury Prison Suite with fancy amenities (not by normal standards anyway), as these fancy suites are for mob bosses and influential CEOs convicted of insider trading. At the same time, the prison they seek will not be a Hellhole Prison either; it will be the lowest-security prison that they can use their connections to arrange.
Often goes hand-in-hand with Self-Restraint. Compare Not Used to Freedom (where the character simply doesn't know how to cope outside the structure of the institution), Prefer Jail to the Protagonist (when a criminal deliberately gets sent to prison to avoid another character), and Might as Well Not Be in Prison at All (when being in prison doesn't interfere with their activities). A subtrope of Get into Jail Free and Unishment. Contrast Never Going Back to Prison.
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Wonder Woman (1942): Rebla so enjoyed her stay in prison of Eros that she tried to protest when released, then had the people she was put in charge of build a prison of their own to put her in.
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Small Town Santa: Near the beginning of the movie, local homeless man Raynor comes into the sheriff's office asking to be locked up. He admits to being the one who stole the Baby Jesus doll from the church, which is corroborated by him having it when he comes in. They all know he's doing it because he wants to spend Christmas in the sheriff office jail cell, where he'll have a free meal and a roof over his head. They lock him up anyway, and he spends the bulk of the movie there.
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In Henry's Crime, Max is a Con Man who has grown far too comfortable with the familiarity and security of his "idyllic" life behind bars, to the extent that he deliberately screws up his parole hearings so he will not be released.
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Death Race: The Old Convict Coach actually completed his sentence years before, but stays in prison anyway because he doesn't have anywhere else to go.
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The Simpsons: In Orange is the New Yellow, Marge is arrested for perceived parental negligence, and finds that prison is a vacation compared to her needy and overbearing family. So much so that rather than giving up her time to read, garden, exercise, and go to sleep early, she discharges a guard's gun just to stay in the big house for longer.
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In Some Guy Who Kills People, Sheriff Fuller asks Ben why he was willing to take the fall for crimes he hadn't committed, and Ben replies that everything on the outside is so confusing that being sent back to the asylum where there is order and routine seemed like a good option.
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Greenfingers: Colin has been in prison for 15 years, since he was 17, and comes to enjoy the gardening group there. He quickly pulls a Get into Jail Free after he's paroled because he's Not Used to Freedom and wants to help with the prison's entry to the garden competition.
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The Shawshank Redemption: The Old Convict Brooks sees prison as his whole life after spending 50 years there, so he even tries to attack a fellow inmate in an attempt to avoid being paroled. When he's released anyway, he soon kills himself.
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Hannibal has a dark variant in "Trou Normand": an aging Serial Killer lets himself be caught because "Prison is going to be a luxury next to the kind of retirement home I can afford."
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Karma Overbalance: In this Recursive Fanfiction to The Karma of Lies, Marinette finally figures how much she screwed up when Adriennote who had his life completely torn apart courtesy of Lila Rossi and his own naïveté, with a hefty side amount of hatred from the citizens of Paris when they discovered he was Hawk Moth's son and hatred from his classmates because he let Lila con them makes clear that he is eagerly looking forward to spend the rest of his life in jail for murdering Lila when he has absolutely jack left of a civilian life. Marinette, who up until Adrien yelled this out was blind about the Invoked Karmic Overkill he sufferednote she seriously thought that it was the proper amount of karma for the whole "take the high road" debacle and his selfish attitude as Cat Noir is outright horrified about it… and how much of Lila's blood is on her handsnote "Karma of Lies ended with Marinette giving Lila an extremely vague Paranoia Gambit to try to curb her con artistry. She seriously did not expected for Lila to march right back to Paris to try to find some way to screw over Marinette and how that means Karma is gonna gun for Marinette next.
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The first episode of Arrested Development ends with Michael discovering that his father is starting to enjoy prison life, since he doesn’t have any real responsibilities and spens his days eating ice cream sandwiches and playing baseball in the yard. Although he changes his mind when a guy gets murdered in front of him and becomes desperate to get out.
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This is a Discussed Trope in the 19th century novel The Mysteries Of Paris. Rodolphe, a nobleman disguised as a workingman befriends two lowly Parisians, "The Slasher", a drifter who is prone to fits of being Ax-Crazy, and Songbird, a Hooker with a Heart of Gold. The thing that convinces Rodolphe of their good nature is that both have never stolen, because of moral qualms. When he questions whether they avoided stealing because of fear of imprisonment, they laugh, telling him that in prison they would have the shelter and regular meals that they don't have access to on the outside.
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Discworld: "Done It Duncan", introduced in The Fifth Elephant, is an inept street thief who makes a career out of confessing to every crime he ever hears about (and many he hasn't), in exchange for the decent food and relative comfort of a prison cell. (The City Watch plays along, since he tends to tell them who actually committed the crime(s) he's confessing to, of the form "It wasn't X that did Y, it was me.")
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C.O.P.S. (1988): Rock Krusher is Dumb Muscle who enjoys the simple life in prison, so he lives there willingly until the next time Big Boss needs him.
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My Name Is Earl: When Earl goes to prison, he meets someone he knew as a child, who has been in prison so long that he sabotages his every chance at parole because he is afraid of life on the outside.
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American Dad!: The criminals from "Man in the Moonbounce" see their prison as a "camp for adults", since they can freely roam the facility and engage in many leisure activities. They actively seek to prolong their sentences as much as possible in order to avoid having to deal with the responsibilities that come with being free men.
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The Shield: A former gang leader is released after a long sentence, but the gang has moved forward with new leadership and he holds low status compared to his time in prison where he was well respected and had several lucrative enterprises. He ends up killing the new gang leader both to get revenge and to return to his life as a prison shot caller.
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In Yakuza 0, Omi Alliance brass Homare Nishitani has his own personal jail cell at the Osaka precinct thanks to his friendships with a few corrupt cops, including his foster father Billiken. As he notes, since there are guards everywhere, and you'd have to go to jail to get at him, it's effectively "the best hideout taxpayer money can buy." When he decides he wants to leave, the jail cell is left unlocked and he can just walk out.
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The First Law: In Best Served Cold, the counting-obsessed convict Friendly spent most of his life in a prison called Safety (because it protects society from its inhabitants) and misses the order and security of that existence, and at the end of the novel, considers checking himself back in. In a later book in the series, Red Country, Friendly is elated when he is arrested along with the other villains of the novel.
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Chowder: At the end of the episode "Lollistops", Chowder and Gazpacho are arrested for the trouble Chowder caused at the dentistry for lollipops. Chowder claims that he would never let food cloud his judgment ever again, but after tasting prison food, he wants to stay there forever, much to Gazpacho's dismay.
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It's mentioned in the lore of Fallout that in the years before the Great War, America was facing major shortages of basically everything, and rioters would attack the police or National Guard personnel, hoping to get sent to prisons where they'd be fed.
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The Onion News Network has Autistic Reporter Michael Falk, who becomes enamored with the rigid routine of prison life when sent to interview a white-collar criminal.
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Heathcliff & the Catillac Cats: Heathcliff's dad Pop loves his life in prison. In "A Piece of the Rock", when he's taken back there, he contently calls it home, and when Heathcliff says he's going to break him out of there, Pop shoots this suggestion down.
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The Loud House: Downplayed, as it's community service and not actual jail, but in the episode "Rita Her Rights", Rita comes to enjoy performing community service as it keeps her away from her chaotic household and allows her to have some peace and quiet.
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Living Dead Girl: Alice's kidnapper Ray threatens to burn down her parents' house with them and her newborn baby sister inside and frame her should she defy him. Alice begins to entertain the idea of going there, getting the family out, and burning it down herself, as not only would she be away from Ray after being caught, but she would have the opportunity to eat regularly (as Ray had been starving her since she hit puberty to keep her looking like a child) and grow into a mature figure, making her less desirable to him.
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In the final case of Trials and Tribulations, after Iris is arrested for murder, Larry, who's smitten with her, contemplates stealing Detective Gumshoe's wallet in order to follow her there, then decides against it because he "can't do that to someone who looks like he's down on his luck."
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The Red Skelton Show: Played for laughs in the adaptation of the O. Henry story "The Cop and the Anthem". Freddie the Freeloader plans to celebrate Christmas by running up a huge bill at a fancy restaurant, admitting he's broke, and getting sent to the relative comfort of prison. However, people keep letting him off the hook out of Christmas spirit. Ironically, as soon as he feels inspired to get a job and make something of his life, he's arrested for loitering.
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A Heist with Markiplier: Yancy is the top dog among the prisoners at Happy Trails Penitentiary who scoffs at the idea of a jailbreak because he believes that he has it better than if he were a free man. He even sings an entire song about it, "I Don't Wanna be Free".
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In one Lucky Luke story (probably "Dalton City"), convict Joe Milton is distressed when he learns he's released for good behavior. To the point that when the Dalton inevitably escape, he uses the opportunity to sneak back in.
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In the Duckman episode "A Room With a Bellevue", Duckman becomes absolutely fed up with the chaotic incompetence, corruption, and overall boorish apathy of everyday life and ends up arrested after a furious public outburst. In court, he pleads insanity, gets thrown into an insane asylum, and learns to enjoy the routine and structure enough that he eventually decides he wants to stay forever.
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SpongeBob SquarePants: In the episode "Doing Time," Mrs. Puff enjoys her time in jail, especially since it keeps her far away from SpongeBob as possible.
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In the Judge Dredd story "Casey's Day Out", the titular Casey is released after a twenty-year Iso-Cube sentence for attempted murder. Unfortunately for him while he was incarcerated the victim of his attempt has grown extremely rich and powerful and is holding a grudge. After dodging half a dozen assassination attempts and barely escaping with his life even with Dredd bodyguarding him, Casey has had enough and pleads with Dredd to take him back to the Iso-Cubes, as at least he was safe there. Dredd refuses, citing the fact that as Casey hasn't broken the law, he cannot legally return him to the cubes. Casey then punches Dredd, as assaulting a Judge is a serious crime with a ten-year sentence and allows Dredd to arrest him so he can be returned to the cubes. Dredd for his part doesn't hold a grudge against Casey (normally anyone taking a swing at Dredd gets a No-Holds-Barred Beatdown), takes the punch that he could easily have dodged, and gives Casey what he wants.
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Played for tragedy in an episode of CSI: an elderly homeless man decides to try to go to jail so he will spend a few days away from the harsh Nevada winter. However, the cop he assaults to try to do so had experience with similar homeless people doing this to him, so he lets the man go while still handcuffed. The cop expected it to be a humiliating but humbling experience for the homeless man. Instead, it gets him killed when he has an accident he cannot get himself out of because of his bound hands, which gets the cop arrested for manslaughter and Grissom bluntly telling him that it would have cost him nothing to offer the dead man a ride to a homeless shelter.
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The Looney Tunes Show: Bugs Bunny and Daffy Duck are both sent to prison for contempt of court, and when they both escape, Bugs tries to convince Daffy to turn them both in, because Bugs thought prison was the best thing to ever happen to him.
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Monopoly: When most of the properties have been bought, it becomes preferable to spend as much time as possible in jail, as you can collect rent and trade without the risks of circling the board.
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Homestar Runner: In the "Blubb-O's Commercial" short, Coach Z (who is usually depicted living in the locker room of a gym) makes aggressive comments toward kids while dressed as the Blubb-O's mascot in a bid to get arrested for this reason.
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Batman: No Man's Land: Many people in semi post-apocalyptic Gotham want to be let into Blackgate Prison, which is much safer than most of Gotham, and at least has food.
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Street Fighter has Cody, the former protagonist of Final Fight who's landed in jail after the game's events for assault. Due to personal guilt and an addiction to fighting, he willingly stays there despite being able to break out at any time with his strength. He only escapes to confront Seth in Street Fighter IV and is finally pardoned in Street Fighter V by Mayor Haggar, who appoints him the new mayor and encourages him to clean up his act.
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Breaking Bad: Saul Goodman hires James Edward "Jimmy In-'N-Out" Kilkelly to do a job for Walt and Jesse. Jimmy feels more comfortable inside prison and offers to be arrested in other criminals' place for a fee, and serve out whatever term they would be sentenced for.
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The following is a list of statements referring to the current page from other pages.

 Desires Prison Life
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Older Than Television
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Prison Tropes
 Batman: No Man's Land (Comic Book) / int_89fab6b
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 Call Northside 777 / int_89fab6b
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