Luxury Prison Suite



""Odds bodkins! This convict penitentiary is really nice! If I ever get arrested, I'll demand to be sent here!""

- Charles Upstart III, DuckTales (1987)

A big-time crook gets sent away to prison, but the forces of law and order can't sever all his outside connections. The character in question has the wherewithal to bribe the guards, walk freely through the prison, have his plumbing and his bedsheets upgraded, eat caviar in his cell instead of baked beans in the lunchroom, etc. Sometimes, the prisoner may actually have all the resources necessary to escape, staying "imprisoned" because there's a particular reason to do so. Or maybe it's because they do something that actually benefits the authorities. Usually occurs with rich crooks; they'll do anything to retain as much as they can of their former big-spending lifestyle.

This is actually Truth in Television, greats like Al Capone, Pol Pot, and Augusto Pinochet were kept under house arrest or housed in very, very nice prison cells.

Compare the Gilded Cage, where an innocent is deliberately confined in an abode luxurious enough not to look like a prison.

Advertising

 * A 2011 Audi commercial features two millionaires trying to break out of a luxury prison.

Anime and Manga

 * Oliva in Baki the Grappler has his own prison cell decorated like a hotel suite, complete with the finest of liquors and 5-course meals. In exchange, though, he helps the police capture crooks.
 * The Penal Colony Lutecia was sent to after Magical Girl Lyrical Nanoha StrikerS. It looks like a summer getaway and has no restrictions on outside communication, visitors, and delivered items. Lutecia's only limitation seems to be that she can't leave the planet. Agito even commented in StrikerS Sound Stage X on how nice the place is when she visited Lutecia  so they could have a picnic there. Unlike most examples, this is less about the prisoner being rich, and more about the prisoner being extremely young and not fully accountable for her part in the terrorist attack. She presumably didn't accept the "Get Out of Jail Free" Card the others did. Magical Girl Lyrical Nanoha ViVid later revealed that it also has a massive personal training camp that Nanoha and crew can occasionally use, complete with a hot spring.
 * The main antagonist in Zettai Karen Children first appeared in one of these. In his case, it is probably not so much about connections as about having ability to teleport stuff in and out as needed.

Comic Books
"Matt Murdock: Nice setup. You get maid service, too?"
 * Kingpin from the Marvel Universe gets away with this every time he's thrown in the cooler.
 * Bonus fun; that nice table? The hollow legs are crammed full of hundred dollar bills. Just in case another bribe needs to happen.
 * Especially in the Marvel Comics 2 Universe, he's depicted in Spider-Girl as having an entire luxury suite in his prison cell. Of course, he gets away with it by being a Magnificent Bastard.
 * The one-shot comic  The Trial of Venom, a crossover between Daredevil and Spider-Man begins with the warden at the Vault giving a visitor a tour of the facility, and explaining the new security (put in after the mass break out in Acts of Vengeance) which includes new holographic technology. She also explains how they're experimenting with a rewards system to encourage rehabilitation, showing Moonstone as an example. She's sunbathing in her cell, which has been turned into a pleasant beach motif using the holograms.
 * A minor character from Alan Moore's Watchmen, the Big Figure, is seen wearing a silk cravat with his prison blues, smoking a big Cuban cigar, and walking freely through the prison accompanied by two henchmen (though it is implied that he's coercing some of the guards for these privileges, as demonstrated when he asks Rorschach's guard about his wife and children and the guard becomes terrified).
 * A variant in Alan Moore's comic book Albion; psychotic British superhero Captain Hurricane is given a life of luxury in prison because, if he entered one of his "ragin' furies", he could tear the place apart. He's kept in line because due to the drugs in his tea he isn't aware he's in prison at all.
 * In the All-Star Superman comic book series, Lex Luthor has an underground cavern hideout connected to his maximum-security jail cell, complete with an attractive ferrygirl to navigate the underground river and a baboon in a Superman costume.
 * When The Joker had his own short-lived series during the 1970s, he somehow had a miniature hide-out constructed beneath his cell in Arkham Asylum.
 * The alternate continuity Punisher series, published under the Max imprint, subverts this in the storyline ''The Cell'. The five that fired the bullets that killed Frank's family are all in the same large cell in Riker's. It looks like any old regular cell, but the narration reveals that they can get whatever the hell they want (except women) and the guards will look the other way. It's implied they could just outright leave if they wanted to. Frank doesn't let them.
 * In one Wonder Woman story Wonder Woman goes to a planet where prison is said to be incredibly pleasant, and everyone goes at 15.
 * Mad Magazine often parodies the kind of prisons white collar criminals and celebrities get sent to.
 * Spider-Man and Daredevil villain Hammerhead has one of these in a recent Daredevil arc.


 * In the next story arc, Mr. Fear uses his designer pheromones to make everyone afraid of him. Effectively making him king of prison.

Fan Works

 * In Light and Dark The Adventures of Dark Yagami, Dark uses his Royal Death Note to manipulate prisoners into doing illegal things for him and then dying in order to get a lot of prison food.

Film

 * Film example: The Italian Job (the original version)
 * A similar situation was displayed in the film Goodfellas when Henry Hill was serving his first prison sentence with Big Paulie and other members of their crew. As the film was based on Henry Hill's memoirs it was exaggerated, but still...
 * Charlie Chaplin ended up in a prison like this in Modern Times. In this case, it was satire of how much worse it was to be living on the streets during The Great Depression.
 * In Cradle 2 the Grave Chi McBride's character had nice rugs, food and a prisoner butler (who was seen preparing food with knives), until.
 * Used mildly in The Hurricane. Rubin Carter began with the privilege of wearing prison hospital pajamas rather than standard uniforms and clung to an ironclad determination not to adhere in any way to the normal prison lifestyle. Over the sixteen or so years of his confinement, prison guards allowed him various luxuries in his cell out of a combination of pity, belief in his innocence, and appreciation for not making as much of a nuisance of himself as he could have. Eventually, his cell was filled with various posters of civil rights leaders, pieces of African art, a typewriter on which he writes his memoirs, a small collection of books, and a miniature stove.
 * In a more subdued example, Andy from The Shawshank Redemption living conditions in prison improves when he helps the Warden with his finances. Andy get his own prison room all to himself, and can customize it with shelves with knick-knacks and posters.
 * The most famous female prisoners in Chicago manage this, through gifts and money sent to them by the public.
 * The main premise of Russian comedy film I Want To Go To Jail is how many Western prisons are like this by Russian standards, hence the protagonist's Title Drop.
 * In Quills the Marquis de Sade initially has a spacious room at Charenton Asylum with books, luxury furnishings, wine and freshly-cooked meals separate from the other inmates. As the film progresses he has these items gradually taken away by the new doctor who runs the institution.
 * In Office Space, Samir is convinced to participate in the scam by being assured that American prisons are like this.
 * Specifically, he was assured they would go to "White collar resort" prison, as opposed to "Federal 'Pound me in the ass' prison".
 * Between his top-notch people skills and extensive contacts both military and civilian, Lt. Templeton "Faceman" Peck isn't suffering during his incarceration for a crime he didn't commit.

Literature

 * In the novel L.A. Confidential incarcerated mob king Mickey Cohen is even allowed to keep a dog in his cell.
 * In Wolves Eat Dogs by Martin Cruz Smith (featuring the cop from Gorky Park) a wealthy Russian crime-boss has bagged the cell that has been fitted out to comply with European human rights laws. Ironically if he didn't do this he'd risk being raped by the hard-core lifers who still control the prison system.
 * Arkady Renko (the cop in question) even jokes about it with the mob boss. When the mobster talks about going on vacation later on, Renko pointed out that if he wanted luxury quarters, good food, and a staff that catered to his every whim, why not stay in Butyrka Prison?
 * In Inherit the Wind a jailed schoolteacher jokes that his cell is more comfortable than the rented room he normally lives in. Similar to the Charlie Chaplin example above, this is not meant to imply that he is getting special treatment, rather that his normal quarters just suck.
 * In Discworld, Lord Vetinari has his dungeons set up like this, for those periodic times when Ankh-Morpork revolts against his rule. Vimes notes that it has been constructed to keep the chaos that ensues when Vetinari isn't in power out as it it is for keeping a prisoner in. Naturally, Vetinari has installed several secret exits, should he want to leave, but for all intents and purposes, it's the safest place in the city. In fact
 * Also, Leonard da Quirm's holding "cell." It's in a secret passageway filled with traps that Leonard designed, and he has a spare key for the door. He's quite comfortable, and Vetinari keeps him supplied with all the paint, wood, metal, and paper he needs.
 * Leonard is an interesting case because he's only imprisoned in the strictest semantical sense of the word. Sure, he's not allowed to leave unsupervised, but as the books note, Leonard is the sort of guy who can't truly be imprisoned unless they find a way to lock up his intellect. What he's got is closer to protective custody; it keeps Leonard's considerable, yet indiscriminate, genius out of the hands of those who would use it for petty, destructive short-term gain, and in the hands of Lord Vetinari, who is occasionally inclined to exploit it for the long-term good of the city, but mostly finds that what the long-term good of the city needs is for no one to actually have access to Leonard's genius.
 * In Codex Alera, The Alcatraz has one of these set aside for special prisoners who are there mainly for political reasons and they want to keep as comfortable as possible. It was originally built by a previous ruler who imprisoned the wife of a powerful noble lord there for treason against the crown, and went there to personally "interrogate" her three times a week. Considering she actually did commit treason, that was pretty much the only way to keep her around as his mistress.
 * In the Australian novel Underground, Leo James ends up imprisoned in the abandoned House of Representatives, and despite being periodically tortured by American agents, he finds it quite comfortable: he has the pick of all the furniture to sleep on, access to the member's lounge and toilets, and just about anything the evacuated members left behind.
 * In Philip Pullman's His Dark Materials, this is the fate of Lord Asriel. He was banished to the North for causing political distress, but was allowed to contract the construction of his own cabin including glass windows (which were very expensive at that time). He even managed to continue the experiments that got him banished in the first place by having materials and equipment smuggled in.
 * One author (possibly Fredric Brown) wrote a short story about a tourist arriving on a distant planet and accidentally killing a local. Because the locals enjoy a very long lifespan, the penalty for murder, even accidental murder, is death at dawn the next morning - until then, the tourist is housed overnight in a magnificent 100-room mansion with all manner of luxuries, food, liquor, and even women provided to meet any imagined need for his last night. When he asks how long he has to enjoy all this, the answer is that a full day on this planet equates to "only" about 120 Earth years, so he only has about 60 years to live; as the story ends, he wonders out loud if he'll make it.
 * In The Divine Comedy, Hell itself has a place like this for the Good Pagans, mortals who committed no real sin but were born before Christ or died unbaptized (which was a big thing in Catholicism at the time). Basically, the place is a beautiful meadow where the only unpleasant part is lack of Hope and boredom; the occupants discuss philosophy and art via meditation and from each other. Residents include Electra, Hector, Ovid, Homer, Horace, Lucan, and of course, Virgil - all writers Dante admired. Julius Caesar is depicted as ruling the place from a magnificent throne; he was a ruler Dante revered, and is thus given a position Dante feels he deserved. Virgil claims than residents here can and have be admitted to Heaven eventually, former residents including Adam, Abraham, Moses, Abel, Noah, David, and Rachel, among more obscure Biblical figures.
 * In Vigor Mortis, after Jelisaveta becomes an inquisitor, her first assignment is to work at a correctional facility. There are a few key differences between this facility and what we think of as "prison": The goal isn't to punish the inmates, it's to "rehabilitate" them, though as of November 12th, 2021 it's not yet clear if this means the must inmates be helpful to society, or if it specifically means serving the organization that had them imprisoned. Jelisaveta was surprised by the comfy conditions the inmates were kept in - of course, the more dangerous the inmate, the less comforts they're offered (like privacy).

Live Action TV

 * Harry Grout in Porridge (BBC prison comedy from the 70's). His assigned job is to clean the swimming pool. Slade Prison has exactly 0 swimming pools.
 * In one episode Grouty asks Fletcher if he follows The Archers. Fletch explains he doesn't, on account of them not being allowed radios in their cells. "Really? No-one ever mentioned it to me."
 * The Master, during his imprisonment in the Doctor Who episode "The Sea Devils." The Doctor had evidently pled that he be made very comfortable in captivity, as he meant for him to be there rather a long time.
 * In a novel set after his capture, but before he was placed in a prison with hypnotism-resistant guards, the only reason he's hasn't escaped is that he doesn't want to just yet. He's quite put out when his allies "rescue" him, because that wasn't in his plan.
 * Simon Adebisi from Oz outfits his pod this way after Unit Manager Querns makes him a trustee.
 * Also the inmates in the AIDS ward are allowed pretty much what they want, as the guards figure they're dying anyway.
 * Dale the Whale in Monk has his own personal cell and lives with a certain amount of luxury. This is partly due to his massive wealth and influence and partly due to his massive size. But when he tried to assassinate the Governor of California as part of a plan to get himself pardoned and to put Adrian Monk in jail, he had all his luxuries taken away.
 * Seen in Season 2 of The Wire, all of which drug lord Avon Barksdale spends in prison. He manages to maintain control of his business, take over the supply of drugs flowing into the prison, and spend his free time playing video games and eating KFC.
 * Mayberry Jail in The Andy Griffith Show features Aunt Bee's home cooking, lace doilies on the bedstands and a key left deliberately within reach of the cell so that Otis, the town drunk, can let himself out when he's sobered up.
 * Subverted in one episode: after arresting some real criminals leaves the prison full, Otis is put in Aunt Bee's custody - the Taylor house quickly gets named "The Rock".
 * Khan lives in one in the MacGyver episode "The Escape".
 * Battlestar Galactica. At the beginning of Season 3, Athena's previously-stark cell is shown to be fitted out with curtains and furniture, indicating her change in status from hated Cylon prisoner to trusted advisor to Admiral Adama. According to the podcast commentary, the "prisoner with privileges" trope was specifically referred to in the script.
 * It's later revealed that cylons have the ability to image themselves in surroundings that are far more intricate, making all this 'luxury' unnecessary—except as a means of making Athena's jailors think of her as something other than a machine.
 * Red Dwarf. After being reprogrammed into a ruthless TV executive, Kryten is seen with a cell full of luxuries, with the guards calling him "Sir".
 * Whether it's the same one isn't mentioned, but Lister says there's a luxury block which prisoners can use as a reward for good behaviour.
 * Used in several episodes of Leverage. In one, they have a witness who is in jail. They offer to break him out if he helps them. He laughs at them, because he is quite happy in the minimum-security prison. So they frame him as the leader of the Aryan Nation and threaten to send him to a maximum-security prison if he doesn't give them the info they need.
 * One of the transferred employees from the Stamford branch of Dunder-Mifflin makes his time spent in white collar prison sound so good that the Scranton employees got jealous.
 * On Parks and Recreation, Leslie gets arrested in Pawnee's upscale rival town Eagleton. Eagleton is so rich that their jail includes guards who act more like waiters and there are prison gift bags.

Theatre

 * In The Beggars Opera, Captain Macheath pays to make his stay in Newgate Prison considerably more comfortable, with no chains and excellent food.
 * In William Shakespeare's Richard, Duke of York (commonly known as the Henry VI, part 2), Richard's son Edward is imprisoned by the Bishop, but apparently so well-treated he is allowed to go out hunting. That's how he escapes.

Video Games

 * Police Officer Marcus Reed's crime boss father in True Crime: New York City
 * Pictured above: In Apollo Justice:Ace Attorney, after is convicted of murder and sent to solitary, he still manages to receive presents, which include: a bookshelf full of novels, little artsy knickknacks, a bottle of the best nail polish on the market, and a comfy chair that's at least 10 times as expensive as the other chairs in the prison. Talk about connections.
 * The Special Prison in Ghost Trick seems relatively cozy. The rock star can keep his instruments and Jowd can paint as much as he pleases. He even gets giant roast chicken for dinner... though then again
 * Also, the other two prisoners (the rock star and Sausage Head)
 * The prison cell that holds Lucretia Merces in Suikoden V is like this. She explains that it was originally a cell for incarcerated royalty or nobility, and ended up in it herself due to her services for, well, royals and nobles (the extreme respect that a few of the guards have for her certainly doesn't hurt).
 * When the protagonists of Shadow Hearts: From the New World bust into Al Capone's prison cell they find that it's well-furnished and quite comfy, as a nod to the Real Life situation mentioned below.
 * In Remember 11, Inubushi Keiko (a mass murderer), lives in relative comfort at the SPHIA facility. Justified in that SPHIA was built as a psychiatric hospital, rather than a prison.
 * In Dwarf Fortress, this can be an effective way of keeping dwarves sentenced to imprisonment from getting too upset. Keep them locked up with a high-quality golden chain and the prisoner will be too busy admiring the craftsdwarfship of it to get too worked-up about their predicament. Giving the dwarf good food and drink can also help.
 * In Skyrim, Sibbi Black-briar is given an eight month sentence in a luxurious "cell"—an actual bed, gourmet food, etc. -- for committing murder. This is thanks to his mother Maven being one of the most influential and powerful people in Skyrim. And he still has the gall to complain.
 * During the introduction of Mass Effect 3, Shepard half-jokes that being detained isn't so bad "once you get used to the hot food and soft beds." What little we see of Shepard's cell features floor-to-ceiling windows looking out on the city, and since nobody bats an eyelash at Shepard walking around unrestrained, we can assume s/he's been given freedom to move about.

Web Original

 * In the SCP Foundation, a lot of SCPs are contained this way, often because the only way to keep them contained is to ensure they do not want to leave. Some well-known examples:
 * SCP-082 (aka Fernand the Cannibal) believes he is the King of France. Because it seems impossible to kill him or hold him in any sort of restraint (and is very dangerous, especially if angered), the Foundation enforces this delusion. His spacious living accommodations have the appearance of a luxurious palace, he is given any amenities he desires (like television, movies, books, and gourmet food), and anyone who speaks to him (mostly D-classes) are instructed to address him as they would actual royalty.
 * SCP-053 (“the Small Girl”) is a child suffering a curse that makes her unable to grow older, and inflicts a Hate Plague on anyone who touches her or stays near her for longer than 10 minutes. Her cell is more or less a comfortable child’s room, and she is given toys, books, and games typical of a five-year-old, with the food provided being prepared by her request.
 * The Foundation is more cautious with SCP-166 (the “Teen Succubus”), but she is still given a suite with comfortable furnishings and provided with any requests she makes, within reason (such as a Bible, other books, rosary beads, and occasional use of a telephone to call the nuns at the convent who raised her as a child). She’s even allowed a furlough every month, although where she goes is marked [DATA EXPUNGED]. So long as only female researchers and doctors interact with her, there is little risk.
 * With SCP-343, Foundation members are told to pretty much give him whatever he wants. He claims to be God (whether true or not is debatable, but he clearly has god-like powers), and could leave any time he wanted - nobody wants that, seeing as he's a font of wisdom who loves giving advice or moral support to anyone who asks. He's also used his considerable Reality Warper powers to refurnish his cell, making it Bigger on the Inside, with expensive-looking furniture, art, and a working fireplace - despite no connecting chimney.
 * Possibly the most unfair example is SCP-056; despite having murdered 17 SCP operatives and dozens of civilians while resisting their attempt to contain her (though they ultimately did) and despite being incredibly rude to the researchers and staff, she is given anything she wants other than weapons, communication devices, and internet, and her cell has things like a king-size waterbed, Jacuzzi, plus any food or entertainment she desires. The reason for this is simple - what makes her dangerous is the fact that Anything They Can Do, She Can Do Better, literally. If she were to be punished, disciplined, or held with hard-restraints, she'd quickly adjust and be able to do it better than they could, assuring she would escape her cell with thoughts of bloody revenge on her mind...

Western Animation
"Bonaparte Beagle: Oh, guard! Go pack our bags and tell the warden we've escaped for a week or so."
 * In Megamind, the main villain is in prison so often that he has turned his prison cell into this, complete with pictures, painting on the walls, sinister chair, TV and so forth.
 * He grew up in that prison. First he just landed there, but then the fucked-up logic of the setting meant that as a three-year-old participating in a prison break, he was sentenced to jail time instead of being put into the foster care system.
 * Darkwing Duck:
 * Taurus Bulba in the pilot episode; he connives behind the guards' backs instead of bribing them. He takes this trope Up to Eleven. His cell is capable of transforming into an executive office, complete with secretary and outside phone line. Then later on you find out he's turned the entire prison into his own flying fortress.
 * Also done in one episode where Darkwing spies on a villain in a minimum security prison. There's literally no fences or walls, only a loudspeaker thanking the prisoners for not leaving.
 * The super-maximum-security prison that other super-villains are sent to isn't like this, but Quackerjack seems to enjoy being there anyway. As Megavolt remarks to Liquidator and Bushroot when they're all on work duty, "Someone should tell Quackerjack that prison isn't supposed to be fun."
 * Ricochet Rabbit had one episode where he has to evict a cowboy prisoner who is quite happy right where he is, in the county prison. "Where else can I get a room and three square meals a day, for free?"
 * Guitierrez in Freakazoid! gets away with this. Except for his toilet. He bullies the warden into giving him everything he wants, including an internet connection.
 * John Corben, before he becomes Metallo, in the DCAU Superman animated series. He has what he has because he didn't rat out Lex Luthor in the first episode, and Luthor makes sure he's well taken care of... so to speak.
 * When Superman needed the Parasite's help to find a bomb, the Parasite was offered a tv inside his cell in exchange for his cooperation.
 * In The Simpsons, Homer, as a prison snitch, gets things like a plasma TV, a "Snitch Life" bling chain, and even a Segway from his "Mother".
 * Another episode has Mayor Sideshow Bob sent to Minimum Security Prison for rigging his election. Per its name, it looks more like a college campus than a prison. Given that the local prison Harvard rowing team asked him to join up for a match against Princeton, its likely that the place is a prison for "white collar" criminals like corrupt business men or, in Bob's case, a corrupt politician.
 * In another episode, when Kirk Van Houten was arrested, Chief Wiggum told him the cell he's going to wouldn't be so cold and damp as Van Houten's apartment. In fact, a normal prison cell felt like the trope for him.
 * In Home Movies, Brendon's class is taken on a field trip to a prison as part of a Scare'Em Straight program. However, they took them to a white collar prison, which the kids considered akin to this trope. Coach McGuirk even remarked that the cells were better than his apartment.
 * Gargoyles: Xanatos himself had a private cell on Riker's Island to plot his next scheme. It was no larger than an ordinary prison cell, but it was very nicely appointed, making it more cozy than confined.
 * The above quote is from the 1987 DuckTales cartoon episode "The Status Seekers". Charles Upstart III visits one of these to hire the help of the Beagle Boys who reside in this prison.


 * In one episode of Dexter's Laboratory, his Dad wouldn't hire cable tv, which prompted Dex into building a satellite that (illegally) brought extra channels. When the authorities learned about the fact, they blamed and arrested Dad. When Dexter's Mom went to the Precinct where Dad was taken to, she was told he could have left hours ago. Dad was then shown enjoying his cell's tv.
 * DC Animated Universe examples:
 * John Corbin (before becoming Metallo) has this, a "reward" from Lex Luthor for not turning stool pigeon. Unfortunately for him, this also makes Luthor think his loyalty makes him the perfect recipient  of a procedure that  Corbin eventually regrets...
 * When Superman needed the Parasite's help to find a bomb, the Parasite was offered a TV inside his cell (with cable, including the premium channels) in exchange for his cooperation.
 * In the episode "Where There's Smoke", Volcana was spared a regular prison and instead isolated on an island, where Superman brought her supplies (this was both for extenuating circumstances and for the protection of other inmates, given her powers); it seemed a tropical paradise, so long as she stayed put, but she clearly did not. She was later seen fighting Supergirl, and later sent to a high-security section of Stryker's Island Penitentiary.
 * The Ultrahumanite has one of these in Justice League, albeit a relatively small one. Gourmet food, classical music, TV, books, he has to be heavily bribed by Lex to even consider escaping.

Real Life

 * Surprisingly enough, Adolf Hitler. After the Beer Hall Putsch he was tried for high treason and sentenced to five years in Festungshaft (literally "fortress confinement"). Festungshaft was a type of jail that excluded forced labor, featured reasonably comfortable cells, and allowed the prisoner to receive visitors almost daily for many hours. It was the customary sentence for people whom the judge believed to have had honourable, but misguided motives. While in prison, he dictated most of the first volume of Mein Kampf.
 * Sharashka's, special prisons in the Soviet Union's Gulag System. As seen in The First Circle they were used to coerce political prisoners with useful scientific and engineering skills. Do well enough and you'll get released. Do bad, and you get kicked down back to the normal prisons.
 * A fair number of nobles ended up imprisoned like this. In the Middle Ages, the noble may be related to his captor, and nobles were held prisoner primarily to obtain a ransom. Besides, you never knew if your prisoner would one day be holding you hostage. Better to treat him well and hope he'd return the favor in the future.
 * In Real Life most countries operated this as policy (i.e. you had to pay for most things and the more you paid the more you could get) up until round about the 1700 to 1800 period.
 * In the real world, cocaine king Pablo Escobar's personal quarters were so good that La Catedral, the prison he was held in, was dubbed the Hotel Escobar.
 * Although to a lesser extent than the Pablo Escobar example, Al Capone's cell during his eight-month stay at Eastern State Penitentiary was noted by the gangster as being "very comfortable." It included Oriental rugs, fine art, and a state of the art radio receiver. He couldn't keep it up in the federal prison system after his tax evasion conviction, however.
 * In his memoir Wiseguy (which was adapted into the film Goodfellas), Henry Hill goes into detail about the time he served at Lewisburg Federal Penitentiary, which was nicknamed "Mafia Manor." How comfy was it? Mobsters got their own special dorm, which was described as looking like a Holiday Inn. Mobsters were allowed to cook their own meals made from gourmet foods smuggled in by the guards. Mobsters didn't have to work if they didn't want to; if they did (for the pay), they could get someone else to do it. And mobsters could use the phone whenever they wanted, and one mobster stored the drugs he was selling in the chaplain's safe. The place was so nice, you couldn't even get in unless you greased the palm of the bureaucrat in charge.
 * Yet another real life example comes from the mid-19th Century. Boss Tweed, an infamously corrupt New York politician was said to have his own cook and could even come and go as he pleased while in prison.
 * And another real-life example was the system of debtors' prisons in England during the Industrial Revolution. They were notoriously corrupt, and while the truly broke had to beg passersby for food (meals weren't included unless you could pay the guards), wealthy and well-connected inmates had furniture and meals brought in from outside, got drunk, had prostitutes brought in at all hours, and generally enjoyed a standard of living that only the landed gentry could afford.
 * A caveat noted in Thackeray's historical novel Henry Esmond, is that while the wealthy like the title character could afford a comfortable confinement, it was at a truly exorbitant price. When their money ran out...
 * This sort of thing is very common in developing countries. Corrupt politicians practically take over the prisons where they're sent.
 * During the War of 1812, American prisoners of war were held in Halifax and allowed to wander around the city as they pleased during the day so long as they returned to their cells in the evening. Not a single man even attempted to flee, and many of them stayed in Halifax after the war ended.
 * This was not especially unusual in that era, at least not for officers. An officer who gave his word not to attempt escape might very well be allowed free run of the city he was being held prisoner in. And, being an Officer and a Gentleman, he (usually) wouldn't try to escape.
 * Taken a step further in the American Civil War. At times when holding or exchanging prisoners of war was unfeasible, captors would often grant prisoners a parole: They would be flat out released and free to go in exchange for signing a paper saying that they will not take up arms against their captors again. Of course, if you got caught violating your parole, then things get ugly.
 * This system broke down later in the war, once Grant and the Union realized that a manpower shortage was the South's greatest weakness. They held onto their prisoners, the Confederates responded in kind, and by the end of the war POW camps on both sides were some of the nastiest prisons to be seen until the 20th century.
 * During WWII, Italian prisoners of war kept at a camp in northern New Jersey were frequently given weekend passes to stay with Italian families living in Philadelphia.
 * More Truth in Television - Minimum security prisons are more comfortable than max-security ones, for obvious reasons. Oh, and there's that Austrian Max-Sec prison that looks like an art college dorm...
 * Of course, most people who get sent to minimum security are nonviolent and used to a high standard of living on the outside (tax evasion, securities fraud, embezzlement). Simply being deprived of their freedom is a huge blow, not to mention the social stigma. Besides, if they misbehave they can always be sent somewhere worse...
 * Well-behaved prisoners and convicts of other nonviolent crimes even in medium-security facilities are allowed privileges such as books, art supplies, writing materials, and even non-uniform clothing. However these usually must be earned and can be revoked should they act up.
 * Martha Stewart was sentenced for misleading federal prosecutors. She spent some of her sentence in a minimum-security prison, and some of it under "house arrest." Bearing in mind that Martha Stewart lives in a very nice town in New England and has built an entire career around telling people how to make their homes elegant and comfortable, it stands to reason that "house arrest" for such a woman would hardly be a punishment, right?
 * Bastøy Prison in Norway is basically an island with just over a 100 inmates on it, accessible by ferry. The inmates walk free and spend most of their time working the island farms. Even the ferry is operated by one of the inmates and during the night there are only five guards. While most of the inmates are non-violent, there are some with murder convictions. The most bizarre case is the man who killed another person with a chainsaw. He's the one in charge of all the land clearing on the island, due to his tremendous skill with the chainsaw.
 * The Tower of London was historically used as one of these.
 * Napoleon on Elba, where he was made governor and given a 600-strong guard. After Waterloo, he spent the rest of his days on Saint Helena in a nice English-style manor.
 * Justified, because the British exiled him not to punish him so much as to just get him out of their hair.
 * Alternately, for a man used to having half of Europe at his personal beck and call, the very fact that he was isolated on a rock in the middle of nowhere with no way to fulfill his ambitions was punishment enough.
 * Al Capone, finally convicted on tax related charges, began his sentence in a prison where his money and fame brought him all the finer things in life, including the ability to leave if he wanted to. Unfortunately for Al, it all came crashing down when the guards told a visiting official that he was out, but was supposed to return later. Then he was transferred to Alcatraz, had the crap beat out of him by inmates, and eventually lost his mind to dementia caused by syphillis. Which then killed him when he got out. So... crime doesn't pay if you have an undiagnosed case of syphillis
 * When she was imprisoned for tax evasion, "Queen of Mean" Leona Helmsley hired and bullied fellow inmates into waiting on her hand and foot, just like when she ran her hotels. One even served as her personal secretary.
 * Despite having the reputation of a Tailor-Made Prison, the famous Bastille in the pre-Revolutionary France was actually designed to be a prison made of this trope. It was next to impossible to escape, and the inmates' identities were a carefully guarded secret, but most of them were political prisoners and noblemen who had caused embarrassment to someone of higher status, most of whom could expect to be released when their families paid the right people. Some even arose to high positions in the government after their release, so the wardens were extra careful on how to treat prisoners who could one day become their immediate superiors.
 * Brazilian former Judge Nicolau dos Santos Neto, who was arrested and convicted for embezzling funds from the building of a courtroom, is occasionally transferred from prison to house arrest on the pretence of treating a depression case.