Freeman plays "Red" Redding, a lifer who knows the ropes at Maine's 'Shawshank State Prison'."You'll find him in just about every prison film and television series ever made. He's the old convict that's been inside as long as anyone can remember (maybe he even received a Longer-Than-Life Sentence). He knows everything there is to know about how the prison works, and can explain it to new inmates. He tends to have the respect of most of his fellow inmates (except maybe the Ax-Crazy psychos). Oftentimes no-one (except himself) knows just what he did to end up here, and wonders just why he belongs in jail. If the central characters decide to break out, the Old Convict probably won't go with them, realising he no longer knows how to survive in the outside world. He may die at the hands of the authorities or vicious fellow inmates (maybe in an attack actually aimed at the hero), inspiring the heroes to either escape or seek vengeance. Compare the Almighty Janitor. Only occasionally related to The Con or the Con Man.
— From the DVD blurb for The Shawshank Redemption
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Anime and Manga
- Anchan in Rainbow: Nisha Rokubou no Shichinin, relatively speaking. He's just a teenager, but he's been in prison longer than the others, and he functions as a mentor figure.
- Ben 99 in the 2000AD serial Harry 20 on the High Rock. Seemed more than a little stir crazy. Turned out not to be what he seemed, in more ways than one.
- Curly in Hard Time is the oldest lifer in State. Coincidentally, his cellmate is the youngest — 15-year-old school shooter Ethan Harrow. Curly went into prison in his early 20s, and by now is your typical crotchety old man, having come to terms with the fact that he'll never be free again. That is, until his long-lost granddaughter managed to get him out on appeal.
- Curly isn't much of a mentor, and largely doesn't even consider Ethan his friend. Instead, the mentor role is split between two other inmates: Cole, a thirtysomething career criminal who's been in and out of the joint all his life; and "Fruitcake" Mullins, who is around Curly's age but serving a much lighter sentence. Oh, and Fruitcake is the only principal character to die of natural causes in prison.
- The Distant Finale reveals that Ethan himself served his full 50 years, though he notes that after the first 10 or so he stopped making friends and just did his time quietly.
- In Y: The Last Man, it is discovered that the idyllic if somewhat secretive hamlet Yorick and company stumble across a few months after the gendercide is populated by inmates of the women's penitentiary just down the road that the remaining guards cut loose. The white-haired woman with a cane and fond memories of working munitions factories during World War II that was more or less running the place? Doing life for murder.
Film - Animated
- Chatter Telephone in Toy Story 3. He has been at Sunnyside Daycare Center for the longest time. Even before Lotso Bear took it over. To help Woody and his friends escape the daycare center, Chatter Telephone detailedly describes the layout of the daycare center and warns Woody that the only way for a toy to escape is to neutralize the Cymbal Monkey's surveillance system.
- "Jack" Andy Beanstalk who Puss meets in prison in Puss in Boots. He provides useful information about "the Great Terror".
- Jafar disguises himself as one of these in Aladdin, in a Monte Cristo reference.
Film - Live Action
- Coach in Death Race. His sentence was actually over years ago, but he stays in prison because he has nowhere else to go.
- English from Escape from Alcatraz; a black inmate serving two life sentences for killing two white men in self-defense.
- Frank Perry in The Escapist. He is a lifer and has long accepted that he will never see the outside again. Events conspire to cause him to rethink this and start planning an escape.
- Fergus Wilks (David Kelly) in Greenfingers. Fergus is the one who introduces Colin to gardening.
- Over the course of the film Life (Eddie Murphy & Martin Lawrence) the two characters become this over the course of decades of incarceration.
- Pop in the original version of The Longest Yard, called Skitchy in the remake, who remains in prison far past his original sentence for having struck a guard who later became the warden. Crewe asks him if hitting the warden was worth an extra 20 years — Pops/Skitchy hesitates momentarily and says it absolutely was.
- The equivalent character in the British remake Mean Machine is Doc, who teaches Meehan everything he knows about the prison's goings-on.
- Slammer in Micmacs, who introduces himself by saying that he's been in prison for 3/4ths of his life. He uses his status as an old-time prisoner to distract some drug dealers long enough for Bazil to steal their heroin.
- The Shawshank Redemption: Ellis Boyd "Red" Redding. Also Brooks, though he doesn't seem to be quite as prison-savvy as Red. Or at the very least, it's not as obvious.
- There's the choral conductor in the Korean film Harmony. She is able to organize the ladies of the prison into a group (not gang).
- Genflou, from the 1952 film version of Les MisÚrables; a character who is not in the novel and was created to fill this role in the film version.
- Stroud in the latter half of Birdman of Alcatraz, having grown into this role over the course of his years in prison.
- The original Zorro becomes one of these in The Mask of Zorro, after he gives up hope when he is arrested, his home destroyed, and his wife and child apparently killed. After twenty years, though, he finds the strength to break out.
- Fortress (1992): Abraham has been in the prison so long that he's become a 'trustee', a privileged inmate who is entrusted with some responsibilities by the guards. Brennick tries to ask him for help, but he's so jaded that he would rather keep his head down. He does eventually aid the heroes when he realizes that he'll never be allowed to leave by the prison director.
- 'Low Key' Lyesmith in American Gods by Neil Gaiman. Like many other examples, there is more to Lyesmith than meets the eye.
- Older Than Radio: Abbe Faria in The Count of Monte Cristo by Alexandre Dumas (and its various film and television adaptations). He teaches Dantes everything he will need to know for his new life on the outside, tells him where a fortune is hidden, and his death provides Dantes with his means of escape.
- General Jan Dodonna in The Krytos Trap serves this purpose for the captured Corran Horn in Ysanne Isard's Lusankya prison. Though he doesn't go not because he doesn't know what to do, but because he's the highest-ranking Rebel prisoner, knows they can't get the other Rebels out, and also knows that if he escapes without them she'll have them killed.
- In Donald Westlake's Help, I Am Being Held Prisoner!, the protagonist is an inveterate practical joker who is in jail after a prank gone wrong. His Cellmate is an archetype old con provider of good advice.
- Babe Fraser in The Stars' Tennis Balls by Stephen Fry. As this novel is a re-imagining of The Count of Monte Cristo, this should not come as a surprise.
- In Darkness at Noon, while Rubashov has been in other prisons before, and No. 406 had spent twenty years in another prison, No. 402 has known this particular prison for years.
Live Action TV
- Francois Villars in the MacGyver episode "The Escape". He explains to Mac how the prison works but does not accompany him when he escapes.
- When Earl is in jail in My Name Is Earl and looks for a gang to join, he finds that the Old Con gang aren't any more adapted to survival inside the prison than anyone else.
- Bob Rebadow in Oz. Despite his delusions, Rebadow seems clued into everything that goes on in Oz.
- Minor character Whitney Munson has been in even longer, 52 years compared to Rebadow's 32. He's serving a 110 year sentence for strangling a prostitute and possession of opium.
- Miguel Alvarez's grandfather Ricardo has been in the longest - 54 years as of his final appearance. He dies of Alzheimer's Disease in season 1.
- The Villain of the Week of one episode of Lois & Clark was a bank robber who had been in prison since the Great Depression. After he breaks out a guard mentions a workplace legend that they built the prison around him.
- The villain of the Season 1 finale was also a former gangster who spent most of his life in prison after being betrayed by his partner- he was also imprisoned in The Thirties, and got out a month before the events of the episode. Both of these episodes were broadcast in the mid-nineties.
- Fletcher. Although Fletch has been in and out of prison his entire life rather than spending most of it inside serving a single sentence, he still fulfills the role of explaining the system to newcomers.
- A more conventional Old Con is the very ancient Blanco. When we first see him, he's completed a replica of Muffin the Mule in the prison workshop: "You know, him what's on television." (Muffin the Mule was broadcast from 1946 to 1957. The Porridge episode was broadcast in 1975.)
- In he sequel series, Joe Lotterby is a former bank robber who used to hang out with the Kray twins and has been in prison for decades after accidentally running over one of his accomplices. To put it in perspective, he served time with Fletch during the original series, and is now currently cellmates with Fletch's grandson Nigel, he's lost count of how long he's been inside.
- Jarod meets one in an episode of The Pretender when he's trying to help a wrongly convicted murderer.
- D.B. Cooper, alias Charles Westmoreland, in Prison Break. He is introduced as Fox River's longest-serving inmate (thirty-two years) and he tells Scofield that he has sixty more years left on his sentence.
- Randall spent time in the old cell block and gave the Winchesters information in the episode "Folsom Prison Blues" (S02, Ep19) of Supernatural.
- On Orange Is the New Black, Miss Claudette Pelage is this. She is in jail for murdering someone who raped one of her employees. She ends up getting even more time after attacking a guard.
- Prisoner: Cell Block H had Lizzie Birdsworth, an elderly, chain-smoking, alcoholic recidivist prisoner, who provided much of the series comic relief. At the series start, Lizzie had already served twenty years in prison. When she is eventually released, she finds she cannot cope with life on the outside and commits a series of crimes to get herself re-incarcerated.
- Robin of Sherwood has the nameless insane old prisoner in the dungeon of Nottingham Castle, who constantly refuses to join in escape plans because he doesn't want to leave his pet rat Arthur. He was initially created as a plot device for one episode, but became an Ensemble Darkhorse.
- In The Chronicles of Riddick: Escape from Butcher Bay, Riddick encounters an old prisoner in the Single Max section, who among other things asks Riddick what his first kill was like ("that's between me and him" being Riddick's answer), and offers Riddick a reward if he gets rid of a troublesome inmate. In a Shout-Out to The Shawshank Redemption, he's named "Red".
- Eddie Gordo's backstory from Tekken 3 is that he was framed by the Mishimas, and while in prison, was trained in Capoeira by the oldest convict interned there. Christie Monteiro is the old man's granddaughter.
- Doyle in The Lydian Option describes himself as the "welcoming committee" - a human who introduces new human prisoners to life in the alien prison and shows them the ropes.
- Ian Starshine fills this role at the gladiator camp in The Order of the Stick; his reference to being nicknamed "Red" is a Shout-Out to The Shawshank Redemption. He's not as reliable as typical examples of this trope, though.
- In Girl Genius, Tiktoffen is the "man in charge" in the sentient, sapient and homicidal Castle Heterodyne. Subverted, as he's actually only been in for three years - but he's still the longest-serving prisoner. People don't tend to last long inside Castle Heterodyne, especially since half the time it's actively trying to kill them.
- Fixing parts of the Castle gives you points and takes months off your sentence, but it's worth noting that in the fifteen or so years that the Castle has been used as a prison, only one person has ever managed to get enough points to get out.
- The Simpsons: 'The last registered Democrat' who helps the Simpsons escape the government re-education centre in the episode "Bart-Mangled Banner".
- In the Family Guy episode "Cool Hand Peter", the gang meets an old black inmate who tells them that depsite the fact they were sentenced to thirty days, they're in the jail forever.
- Age actually can confer status in the prison hierarchy, assuming said old-guy was a life-long criminal who spent much of that time incarcerated.
- In many states in America, especially California, a growing and aging prison population is a serious problem, due to various "tough on crime" measures such as minimum sentences, three strikes and a very low rate of parole. A large number of inmates who were sentenced to life terms in The '80s are now in their fifties and sixties, with all the health problems that come with that, and, since the prison system has an obligation to provide inmates with healthcare, they're becoming more and more expensive. It's estimated that a lifer sentenced when he's 37 could cost the prison system up to four million dollars over the course of his life.