Bane was born and raised in an island prison with a less-than-sympathetic warden. Guess how he turned out...
A short story in one DC comic had a man wrongfully convicted of a crime and sent to Arkham Asylum. By the time the error was discovered and the order to release him was given, the asylum and its unique blend of inhabitants had crushed his sanity.
Andy, from The Shawshank Redemption, is the Trope Namer. Falsely convicted of the murder of his wife, he goes from being an honest banker to using his banking skills to help launder money for the warden. Somewhat subverted in terms of morality, as Andy is secretly planning to escape from prison and expose said warden as a crook, but certainly played straight in terms of lawfulness, as he never breaks a law in his life until after he came to prison, where his crimes are many and varied.
The main character of Blow (based on reality) said this about himself.
In Angels with Dirty Faces, Rocky Sullivan grows up into a notorious gangster after having been thrown into a reform school as a kid for stealing pens, and ends up going in and out of prison well into adulthood due to being corrupted. His friend, Jerry Connolly, escaped being thrown into the reform school by the police, and grew up to become a priest.
In Boys Town, Whitey Marsh's brother Joe, who is on death row, asks Father Flanagan to take Whitey in because Joe sees Whitey starting down the same path he took. Joe is afraid that Whitey will go to reform school and then learn how to be really bad.
In Murder in the First, a lawyer defends a convict accused of murdering a fellow convict, using the trope to try to get the charge reduced to involuntary manslaughter.
In Sleepers, four boys are sent to a juvenile detention facility where horrific sexual abuse at the hands of the guards changes their lives forever. Two of them become hardened gangsters while the other two are able to reintegrate into mainstream society, but all of them are either guilty of or complicit in illegal activities in pursuit of revenge.
In An Innocent Man, Jimmie Rainwood (Tom Selleck) is framed as a drug dealer by two crooked cops that don't want to admit they busted into the wrong house and shot a man who simply walked out of the shower holding a hair dryer. Once he is convicted and ends up in prison, he ends up having to kill another inmate in cold blood to keep the inmate from raping him.
In Caged, a young woman is sent to prison having been an unknowing accessory to her husband's crime. By the end, she becomes a hardened convict and is on the road to becoming a professional criminal.
Sherlock Holmesmentions this phenomenon in "The Blue Carbuncle", when he decides to release the man who stole the title gem: "This fellow will not go wrong again; he is too terribly frightened. Send him to jail now, and you make him a jail-bird for life."
The idea of learning to commit more serious crimes is parodied in Discworld, where the Ankh-Morpork Thieves' Guild, an entirely legal organisation, runs official classes in the city's main prison, the Tanty.
It's played darkly straight in Night Watch, where Vimes muses that Swing had missed the point of laws and the police- he's meant to be taking criminals and turning them into honest men, but instead he's taking honest men and turning them into criminals.
This is the point of the novel and movie I Am a Fugitive from a Chain Gang, based on the real life case of a man wrongly accused of a robbery and sent to the brutal Georgia prison system. After escaping — twice — he is forced into hiding, and in the film's memorable final scene, bids farewell to his former fiancee.
Helen: Oh, Jim. It was all going to be so different.
Jim: It is different. They've made it different. I've gotta go.
Helen: I can't let you go like this!
Jim: I've got to.
Helen: Can't you tell me where you're going? Will you write? Do you need any money? But you must, Jim. How will you live?
Discussed in the Spenser short story Surrogate, regarding a man who was paid to rape a woman by her ex-husband, who met him while teaching a convict education program. Somewhat more ambivalent than many of the other examples.
Spenser: Lot of guys like him in the joint. Sometimes, I suppose, it’s the joint makes them like that. Sometimes being like that gets them into the joint in the first place.
Happens to Jean Valjean at the beginning of Les Misérables. After being released from a very long prison term for stealing a loaf of bread (which was "only" five years until he got it quadrupled for repeated escape attempts), he is unable to find work (because nobody was willing to hire a thief - at least not at a wage he could live on) and is forced to resort to stealing more valuable goods to survive. An unexpected act of mercy from the first person he robs after starting down this path leads to him undergoing a Heel-Face Turn.
Discussed in one of the many Author Tracts in Starship Troopers. When explaining why the future setting of the book uses corporal punishment rather than jail for punishment, a character explains that jails were a place for so-called "juvenile delinquents" to be surrounded by other criminals and learn how to commit far worse crimes than they'd been imprisoned for.
Tobias Beecher in Oz. Imprisoned for vehicular homicide, he is a murderer several times over by the end of the series.
On Homicide: Life on the Street, Junior Bunk Mahoney was a none-too-bright enforcer for his heroin-slinging family, and couldn't stop weeping when the squad brought him in. Fast forward a couple of years, and he's a gleeful sociopath who shoots up the squadroom, injuring several main characters.
Life: When we meet Arthur Tins in season 1, he's a low-rate con artist whom Crews sends to prison. When we see him again in season 2 after he's escaped, he's a hardened criminal who murders one man, robs an armored car and takes a family hostage.
Bones: Serial Killer Howard Epps, possibly. He could be a Manipulative Bastard all along, or maybe he learned it while on death row. When we first meet Epps, he's claiming to be innocent and trying to get exonerated, but it ends up he just reveals he's killed even more people than previously thought, so they have to keep him alive while they process the new bodies. When he returns in season 2, Epps is even more manipulative and playing serial killer games, leading the team on a merry chase with body parts as clues.
When Earl went to prison in My Name Is Earl, he meets a prisoner who's on his list for accidentally being sent to Juvey by him. When he gets out of prison, the public take one look at his shaved head, his prison tattoos and the tough guy persona he adopted inside to stay alive and decide he's a crook. So he lives up to their expectations by becoming one.
Parodied by Stephen Colbert with regards to Guantanamo Bay. He points out that, if someone falsely accused him of terrorism and sent him to prison, he'd come out wanting to kill the people who locked him up. Hence, even an innocent person locked up for terrorism is at risk of becoming a terrorist. Thus, they should stay in detention.
Oliver in the Breakout Kings episode "Steaks". Sent to prison for a joyride that accidentally resulted in a death, he is torturing and murdering people following his escape.
Mr. Bates from Downton Abbey apparently learned some...interesting...skills in prison. Forgery is particularly useful.
Too many brothers, daily, headed for the big pen; niggas comin' out worse off than when they went in.
In The Foremen's song about the failure of the California educational system, "California Couldn't Pay Our Education", in the end, California did pay their education, when it sent them to prison for petty theft, and they learned how to avoid getting caught again.
It's not made clear why Gilby Clarke's character is being sent to jail in "Tijuana Jail." He sticks a switchblade from his boot in a guard's throat to make his escape.
In Dead End, Gimpty recalls that "Baby-Face" Martin Used to Be a Sweet Kid before he was sent to reform school, from which he "came out tough and hard and mean, with all the tricks of the trade." Drina is driven to despair at the thought that reform school will do the same to her brother Tommy.
After being captured in Red vs. Blue, Grif claims this has happened to him and suggests he and Church rob a liquor store on their way home after they're let out... even though he's only been in jail for five hours.
Grif: Time moves slower on the inside. It seemed like seven or eight hours to me.
This article from Cracked discusses how this trope plays out in Real Life. It cites research showing that punishing minor crimes with prison instead of, say, community service, backfires horribly, with the criminals 20% more likely to commit crimes once released. "It's weird-it's almost like prison puts you in a criminal mindset, as if spending all day and all night living with and talking to other criminals, completely immersed in their lifestyle and morals and way of thinking, makes you start to act like them."
In the Zero Punctuation review of Skyrim Yahtzee jokes that the PC of each game was locked up for a minor adventure related crime before becoming a full blown adventurer as a result of their incarceration
In Spider-Man: The Animated Series, this is how The Kingpin came to be — originally sent to prison for larcency, after one of his dad's scams went south and his bulk prevented him from following his father up a fire escape. Once he comes out, he's got 'connections', and uses what he's learned to begin building his criminal empire.
In the Family Guy episode "Dial Meg for Murder", Meg falls in love with a convict, and goes to jail for harboring him after he escapes. When she comes out, she is a lot meaner and starts fighting back against everyone who mistreated her. By the end of the episode, Brian has to stop her from robbing a convenience store at gunpoint.
Wasp, from Transformers Animated, gets falsely arrested as a Decepticon spy in the backstory (shown in a flashback episode). By the time he escapes over half a century later (Cybertronians are long-lived), he's almost Gollum-like in his insanity.
Some gangs actually require members to go to jail before they can join the gang.
This is a common criticism of the war on drugs in particular, or at least the approaches to it that involve prison sentences for the possession of illegal drugs. It is especially often applied to the US, whose prisons are regarded as especially likely to make hardened criminals and whose approach involves locking people up for so much as possessing soft drugs like marijuana for personal use.
Sociologists have been trying to raise awareness of this, asking people to apply the concept of prison to other situations. For example: "If you had a child who was behaving poorly, would it help to take that child out of society, and place them in an environment where they are surrounded, 24/7, by other troublemakers?"
A variation occured in Ireland; in the wake of the Easter Rising, the British army interned large numbers of Irish people who had had little to nothing to do with it alongside the surviving rebels. The combination of unjust treatment and being placed in close proximity to dissidents meant that when internment was ended, the country had the makings of an enormous republican movement.
Stacy Keach is an inversion. He was caught smuggling drugs in The Eighties and sentenced to prison. The warden there wound up being such a positive influence on his life that he's been on the straight and narrow since and based the character of Warden Pope in Prison Break off that warden.
South American serial killer Pedro Lopes started as a petty thief but graduated to murder after getting raped in jail.
Clyde Barrow started as a petty crook prior to meeting Bonnie Parker. He got arrested first for failure to return a rental car, and then for being caught with his brother Buck in a stolen truck of turkey. In 1930, he started a two year sentence at Eastham Prison Farm for robbery. In prison, Clyde was reportedly raped and beat another inmate to death. After he got out in February 1932, his crimes became more violent and more often involved murder. Some theorize that Bonnie and Clyde's crime spree from 1932 to May 1934 was not so much For the Evulz as it was Clyde seeking revenge against the Texas prison system.
John Dillinger was 21 when in September 1924, he and a pool hall buddy named Ed Singleton robbed a Mooresville, Indiana grocer named Frank Morgan. Two days after the attack, Dillinger was arrested, and thinking the judge would be lenient enough to let him off if he plead guilty and apologized, he didn't bother to hire a lawyer. This was a big mistake, as the judge sentenced him to a 10-20 year sentence in Indiana's Pendleton Reformatory. It was in Pendleton that Dillinger met two of the partners who would be by his side during his infamous 1933-1934 bank robbery spree: Harry "Pete" Pierpont, and Homer Van Meter, both of whom were doing time for armed robberies (Van Meter for highway robbery on a train, Pierpont for bank robbery). All three of these guys were soon transferred to the Indiana State Penitentiary in Michigan City, where Dillinger met most of the other men who would be by his side, including Russell Clark, Charles Makley, and John "Red" Hamilton. They all taught him the art of bank robbery. When Dillinger was paroled in May 1933, he immediately started robbing banks in Indiana and Ohio for money that he used to pull off arrangements to smuggle guns into the prison to break out Makley, Pierpont, Clark, and Hamilton.
A concern that some raise regarding mass punishment as is fairly common in the military. Too many folks get in trouble for alcohol-related crimes on the weekend? Let's put tens of thousands of military personnel under curfew, threatening them with punishment if they are caught off base after hours, or even restrict when they can have alcohol in their own homes. Treat someone as if they were the wrongdoer enough times, and they may no longer see any incentive in behaving, and thus develop disciplinary problems.
In 1972, psychologist Phillip Zimbardo conducted an experiment to test if placing normal, emotionally healthy people in a prison-like setting increased their capacity for violence. Half the test subjects were assigned the role of guards, the other half were prisoners. The result both plays straight and inverts this trope: by the end of the first week of the study, both groups had become so hostile to each other that the experiment had to be cancelled.