Might as Well Not Be in Prison At All

""Of course he can get out of there whenever he wishes. He can even be declared innocent if he wanted. But he doesn't do that, because he has no need to leave the building.""

- Bruno Buccellati (in regards to Polpo, a mafia operative), Jojo's Bizarre Adventure

Sometimes the Big Bad is such a Manipulative Bastard that throwing him into prison isn't much of a hindrance to him. It's not necessarily that he's in a Cardboard Prison and can get out at any time, or that he's in a Luxury Prison Suite and thus might not even notice his circumstances. Rather, it's that while he's in prison, he is still capable of leading his organization and moving his schemes against the good guys forward. Prison is just a change of location for him, and won't slow down his evil plot to take over the world for one nanosecond.

In fact, the greatest of chessmasters actually plan for their eventual imprisonment and make getting caught (or even getting killed in some more extreme examples) a part of their overall scheme from the beginning. This way they benefit regardless of their plan's success or failure.

Often combines with a Luxury Prison Suite in the worst cases.

Anime & Manga

 * Polpo, the high-ranking mafia operative from Jojo's Bizarre Adventure, stays in his cell partly because he can still give orders to his men and he can get anything he wants in prison, but mainly because he's so massive that getting him out would be a pain.
 * In Zettai Karen Children, Kyosuke is the world's most powerful psychic. He is kept in a cell that is supposed to block all psychic powers. He has no difficulty leading his esper organization PANDRA from there (even going as far as having some of the members in the same cell without anyone knowing).

DC

 * In the Green Lantern comics, powerfully telepathic arch-villain Hector Hammond's body is imprisoned (he's serving multiple life sentences) and is supposedly under the effects of a psionic inhibitor... but Hammond's mind is so powerful that he can still telepathically control people hundreds or even thousands of miles away from the prison without ever leaving his cell.
 * Pre-Crisis on Infinite Earths Lex Luthor regularly ran his criminal enterprises from the inside of his prison cell. Of course, it was basically understood, if not ever explicitly admitted, that Luthor was in prison only as long as Luthor wanted to be in prison.
 * Batman foe the Great White Shark runs a profitable criminal empire (mostly catering to fellow members of Batman's Rogues Gallery) from inside Arkham Asylum.
 * The Ratcatcher is able to control the massive amount of rats in Gotham from inside of his prison cell.
 * Arkham Asylum is a maximum security mental institution for the criminally insane, holding some of the most dangerously psychotic maniacs Gotham City has to offer as well as numerous superhuman criminals solely because that is the only facility in the state with the capability of holding them. It might go 3 days at a time before at least one of these nutjobs breaks out, kills somebody inside, or before the lot of them take over the madhouse (again), assuming they aren't given early release thanks to the staff being complete incompetents, if not every bit as insane as the patients themselves. The Joker, the one inmate they never want to get out, has transformed escaping Arkham into a fine art and considers it his "home away from home", and has stated many times he lets himself be caught after his latest crime spree so he can be sent back there....in order to relax, recuperate, and plot his next escape and crime spree. Factor in the aforementioned Great White Shark and his cosy business in there, and Arkham is one of the few places that qualifys as both a Cardboard Prison and for this trope.
 * In The Seventies, when The Joker had his own bimonthly comic book, the writers had a conundrum. On one hand, the Comics Code Authority at the time required that villains never get away at the end of a story, to show that Justice Will Prevail. On the other hand, showing a new elaborate escape at the beginning of every issue would get tedious and take precious pages away from the story they wanted to tell. Their solution? Give the Joker an Elaborate Underground Base located directly beneath Arkham Asylum, called the "Ha-Hacienda". He even had a Secret Underground Passage in his cell. Apparently, nobody at the CCA tripped to the Fridge Logic of "punishing" someone by imprisoning him in a place he can walk out of at any time.

Marvel

 * The Kingpin zigs-zags this trope. On the one hand, he is still fully capable of running a criminal enterprise from inside prison and once even tricked Iron Man into eliminating a competitor on the outside for him, able to do so because he still had enough information on the wider criminal underworld to make deals and manipulate the authorities. In a one-shot an ex-con who had been in prison for years remarks that the Kingpin is still the number 1 crime boss in the city after all that time, despite Fisk being behind bars at that point. On the other hand, he's only in prison after Daredevil managed to bring down most of his old criminal empire so what he had was just a shadow of his former glory, and while in prison he had made enough enemies that a lot of guys- even some of his own men- made repeated attempts to kill him. It's blatantly clear from his numerous failed deals and escape attempts that he didn't want to be in prison, and Daredevil as well as the Feds took twisted pleasure in making sure he stayed there every time he thought he was about to get out. Eventually, he only does because his wife convinces Matt to be his lawyer and gets all charges dropped.
 * An unusual version in the Marvel Universe: The Mad Thinker spent several years of real time in an ordinary prison cell—but his brain implant enabled him to project his mind into android duplicates, enabling him to enjoy life and go on the occasional crime spree.
 * Daredevil villain . In addition to the above mentioned Kingpin. Hell, most of Daredevil's higher tier villains...
 * In X-Men Noir, Warden Halloway gives the prisoners at the Welfare Island Penitentiary free rein to do whatever they want - because crime lord inmate Sean Cassidy is running a heroin trade out of the joint and bought him off with the proceeds.

Film

 * The Dark Knight: It was part of the Joker's plan all along to be arrested, because he needed to be inside police headquarters in order to eliminate Lau.
 * Mr Bridger from the original Italian Job ran his gangland empire from his Luxury Prison Suite.
 * In Law Abiding Citizen, Clyde Shelton is a grieving husband and father whose Roaring Rampage of Revenge against everyone involved in the Philadelphia criminal justice system is not even slowed by incarceration in solitary confinement. Eventually, it's revealed that.
 * Corsican mob leader César in Jacques Audiard's Un prophète. His gang and the prison administration obey him; he helps the protagonist, Malik, get day leave so he can run his errands for him. (Well, for most of the film anyway...)
 * In American Me, la Eme gradually takes control over the drug trade on the streets of East L.A. by leveraging their control over prison into influence out in the free world. Granted, this is Truth in Television, as the real la Eme did the same thing...
 * Peter Falk in Undefeated
 * An Older Than Television example, albeit an asylum variant, is The Testament of Dr. Mabuse. Evil Genius Mabuse writes his plans for spreading chaos For the Evulz, and his entranced supervisor passes them on to the outside. So powerful is the will of Mabuse that he commits Grand Theft Me upon death to keep up the work.

Literature

 * In the massive Neal Stephenson trilogy, The Baroque Cycle, Newgate and the Tower of London can look like this: visitors freely come and go and some prisoners have a kind of parole. Humorously, high class is another kind of prison: in the Tower, you are allowed to live on the publicly accessible grounds on the entirely reasonable assumption that leaving is tantamount to admission of guilt and the forfeiture of rank, which latter is tantamount to death.
 * In the Dale Brown novel Wings of Fire it eventually comes to light that  is still a real threat despite having been arrested at the end of the previous book in the series.

Live Action TV

 * Angelus in two episodes of Season 4 of Angel.
 * Dumont, the recurring sociopath hacker from Jake 2.0, could manipulate events, hack computers, and even order hits from behind bars.
 * 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.
 * Hogan's Heroes: The main characters are operate an underground resistance movement out of a German POW camp. They also pretty much run that prison camp in everything but the official paperwork. Not exactly luxury, but they have a habit of leaving whenever they feel like it.
 * In a variant on Hustle, Albert Stroller is kept hostage in a holding cell by a publicity-seeking detective, who forces his fellow con-artists to lure a bank robber into a trap. While he doesn't stay inside long enough to run a criminal empire, Albert quickly befriends the guards by (deliberately) losing poker games to them, then commits a series of crimes inside the gaol to dispose of the false evidence against his crew.
 * 'Genial' Harry Grout from Porridge wasn't necessarily shown to be running any business outside the prison, but he certainly was more in control of the prison itself than the governor was.
 * In The Shield Antoine Mitchell taunts Vic with this fact after Vic accuses him of having murdered. He didn't  He says he could have, but what would be the point, since he has practically everything he had on the outside in prison and killing a cop would blow all that. He punctuates this by giving orders to a nearby prison guard, who calls him "Mr. Mitchell" in response.
 * A group of people in Jonathan Creek decide to kill a murderous escape artist rather than turn him in, assuming that there's little point in putting a modern day Houdini in a jail cell.
 * Megalomaniac Dale Biderbeck is sent to prison in his first appearance in season one of Monk, but he still manages to orchestrate quite a bit of mayhem from behind bars, including.
 * Seemed to be the case in an episode of Psych,
 * David Robert Jones of Fringe leads ZFT from prison and also
 * In the White Collar episode "Payback", Matthew Keller arranges the kidnapping of an FBI agent from his prison cell. He then uses the proceeds of his crime to escape before he can be transferred to a more effective prison.
 * On Once Upon a Time, Rumpelstiltskin is being kept in a magical prison inside a repurposed dwarven mine, but still manages to pull the strings anyway. (Admittedly, he's aided by the prison's Swiss Cheese Security, which allows the Evil Queen to just stroll up to his cell whenever she likes.)
 * A Smallville episode featured people buying strategic places in Metropolis in order to buy the city's natural water supply. Winslow Schott masterminded the whole operation from inside his prison cell.
 * In an episode of The West Wing, some DEA agents are captured by a Colombian drug cartel, which demands that a Pablo Escobar stand-in be released from prison in exchange for their return. The Colombian government is willing to do it, leaving the White House to debate whether to give in to a terrorist demand, with Sam arguing (unsuccessfully) that because the guy has been able to order kidnappings and murders from his cell, it doesn't make any difference whether he's in prison or not.

Tabletop Games

 * In Monopoly, a late-game tactic is to stay in jail for as long as possible. While in jail, you're still free to conduct business as usual - collecting rent from, bidding on or selling properties. Moving around the board has only two major advantages - collecting $200 for passing "Go" and having right of first refusal for landing on an unsold property. But since there are very few unsold properties in the late game and the $200 for passing "Go" is a pittance compared to landing on another player's developed property, Jail is actually the best place to be.
 * There are frequently House Rules to avert this. No collecting rent while in jail, a "pot" where all Community Chess/Chance/tax money goes to the person who lands on Free Parking, etc.
 * Not to mention the very common "no auctioning" house rule, so property that a player chooses not to buy remains unowned at least until the next landing.

Video Games

 * In Batman: Arkham Asylum, we learn that The Joker
 * Bioshock 2:

Western Animation

 * In one episode of Justice League, Batman allowed himself to be captured by the Injustice Gang; he feigned helplessness in order to manipulate one of the Gang's members. He later revealed he could have escaped at any time, but if he did he wouldn't have had a resource "on the inside".
 * The pilot episode of Darkwing Duck had its major villain, Taurus Bulba, running his operation from a prison. He could escape at anytime and he chose to remain in prison because he felt that it was the perfect hideout for him, despite constantly having to deal with an annoying warden.
 * In Gargoyles, David Xanatos spends a few of the early post-pilot episodes in prison for a Possession of Stolen Goods charge. It doesn't stop him from having the Manhattan Clan repeatedly attacked while he sits tight to run out his jail term for that relatively minor charge.
 * As an added bonus, when he got out of prison, whenever someone brought up his criminal record, he would just respond that he paid his debt to society legally; and do they believe in the judicial/correctional system or not?
 * Towards the end of the second season, Tony Dracon turns out to be just as good at running his crime syndicate from his prison cell as from his mansion. It's even implied that he could have ordered a breakout.
 * In Lilo and Stitch: The Animated Series, although the authorities think that Hamsterviel is perpetually trapped in the ceiling of his holding cell unable to do anything destructive, he's actually somehow managed to trick out the dungeon cell with various gadgets, contacts Gantu frequently, and even has objects teleported between his cell and Gantu's ship... all while the prison guards aren't looking.
 * On top of that, the protagonists are aware of this, but do nothing about it. The most egregious case was when he escaped from prison, and after they helped to recapture him they didn't say a word about him communicating with Gantu and just let him be taken back to his tricked-out cell. Sure, Status Quo Is God, but come on...
 * Willy Watt in Batman Beyond was fully capable of exerting his telekinetic abilities to do whatever he wanted wherever he pleased while still being in juvenile hall..
 * In one episode of the western Street Fighter animated series, Bison is captured by a British team of superagents (Cammy was a former member) and sent to prison. This turned out to be a distraction on Bison's part that allowed his agents to enact a scheme that threatened all of England. Bison then forces the British government to hand over a ransom of one billion pounds sterling—all while chilling in his cell and sipping tea.
 * Most of the villains of The Spectacular Spider-Man are like this. Doctor Octopus fakes a return to his old, harmless self and by pretending to have been insane is able to get himself into a psychiatric treatment center that's a lot less stringent than prison would be, and he starts running a criminal empire from there. Most of the other villains do their time in a maximum security Cardboard Prison and go in knowing they only have to bide their time before their underworld connections break them out. Mysterio has a robot double doing time for him, so he literally isn't in prison at all.

Real Life

 * There are, unfortunately, a number of Real Life examples of this; mafia-dons and drug kingpins who continue to run their organization with unabated effect while behind bars, often through crooked lawyers who can pass on orders under the cover of 'Client Confidentiality', or 'bought' cops who can turn a deaf ear.
 * Pablo Escobar, then Columbia's richest man, had a plea deal that meant he hired the contractors to build his own prison, "La Catedral." Rather than be a punishment, being imprisoned basically just meant he had to change his drug business' headquarters to the prison, where he was protected from his enemies and has a staff of people (that is, the guards) waiting on him hand and foot. He allegedly even used the prison to execute members of his crime syndicate who had betrayed him.
 * According to Wola (The Washington Office on South America) this is commonplace in corrupt Mexican prisons where drug cartel bosses often continue their business dealings in relative safety.
 * Prison gangs often make this trope play out in real life. Career criminals on the street have to consider what will happen if they or their friends or loved ones serve time in prison, which, given their activities and lifestyles, is very likely to eventually happen sooner or later. Prison gangs can very often become the most powerful criminal organizations outside of prison, as well as inside, by relying on this fact, and promising retaliation against people who have crossed them on the outside.
 * Minimum security prisons, or "country clubs" as they are often known, are barely prisons at all. They rarely have fences, and aren't always guarded. The prisons themselves are fairly comfortable places (if not as lavish as the convicts are probably used to, more on that later.) The main incentive to stay inside them is that if a convict is caught outside them, they will have to go to a medium security prison. Given that minimum security convicts are generally white collar criminals, who would have real trouble surviving a medium security prison, this is a fairly scary thought for them.