Till the sun is goin' down
Workin' on the highways and byways
And wearing, wearing a frown
You hear them moanin' their lives away
Then you hear somebody say
'That's the sound of the men
Workin' on the chain gang'"
- Sleepwalker fought one group of villains called "The Chain Gang" who took this trope to the extreme, being four convicts who gained superpowers while chained together and who had to stay chained together for their powers to work.
- Batman foes the Trigger Twins were working on a chain gang when they were sprung by woman claiming to be their sister in Robin Annual #6.
- Jonah Hex: Jonah ends up working on a chain gang when he is sent undercover into the state penitentiary.
- The ending of Robin Hood sees Prince John, Sir Hiss, and The Sheriff of Nottingham put to work in one of these.
- The classic movie I Am a Fugitive from a Chain Gang (pictured) is about an innocent man who becomes Exactly What It Says on the Tin.
- Take the Money and Run sees the main character sentenced to work on a chain gang after an unsuccessful bank robbery. One day, his gang decides to make a break for freedom. Hilarity Ensues.
- O Brother, Where Art Thou? begins with Ulysses, Pete, and Delmar escaping from this while chained to each other. The soundtrack during this scene features a work song that was recorded from an actual Depression-era chain-gang. Pete, at one point, is recaptured and put back to work on the chain gang and has to be broken out of prison again.
- Cool Hand Luke worked on one in-between several prison breaks.
- Life (not to be confused with the short-lived TV show with the same name) stars Eddie Murphy and Martin Lawrence as two men sentenced to life in prison for a crime they didn't commit who end up on a chain gang.
- The opening of 48 HRS shows a chain gang in the desert.
- There's one featured at the beginning of The Green Mile.
- Spartacus opens with the title character cracking rocks in the hot Thracian sun.
- In the beginning of Next Friday, Debo and his sidekick escaped prison heading to Craig's house for revenge and both are chained together. They tried to break the chain with a brick but later broke it when approaching in front of Craig and his father's truck leaving the city.
- In The Shawshank Redemption, the corrupt Warden Norton uses the fact that a chain gang is essentially cheap slave labor to undercut local businesses... and then starts taking bribes from those businesses to keep his chain gangs at the prison rather than out working.
- Django Unchained: This is the Fate Worse Than Death Stephen lays out for Django after Schultz ruins their plan of freeing Broomhilda by shooting Candie:
And as a slave of the LeQuint Dickey Mining Company, henceforth until the day you die, all day, every day, you will be swingin' a sledgehammer, turnin' big rocks into little rocks. Now, when you get there, they gonna take away your name, give you a number and a sledgehammer, and say: "Get to work!" One word of sass, they cut out your tongue. And they good at it, too. You won't bleed out. Oh, they does that real good! They gonna work ya all day, every day 'till your back give out.
- Happy, Texas begins with the protagonists' escape from a chain gang.
- The Flower Girl: When Kotpun goes to visit her brother, who is being held in a Japanese prison camp, she sees the inmates building a railway, chained together in pairs.
- In Les Misérables, Valjean and Chenildieu become friends for several years while on on a chain gang.
- In Richard Wright's autobiography Black Boy, one of his memories from his childhood involves him mistaking a chain gang for a row of elephants.
- Sounder: The boy makes his way to a chain gang labor camp where his father is supposed to be, but fails to find him. Lather the father is revealed to have been severely crippled by a dynamite blast while working on the chain gang.
- In Invisible Man, Brother Tarp got the limp in his leg from dragging a chain for nineteen years, six months and two days until he escaped.
- Ben from Carnivŕle escaped from a chain gang before the beginning of the series, and in the first episode is still wearing a broken iron manacle around his ankle. What he did to get there is never revealed to the audience, other than that he's wanted for murder.
- The tap dancers in the opening credits of The Slammer.
- The Dukes of Hazzard episode "Cool Hands Luke and Bo" has the title characters arrested and placed on one of these.
- Sam Cooke's song "Chain Gang" (quoted above) was the second-biggest hit of his career (peaking at No. 2 in the US, No. 9 in the UK), as well as being the Trope Namer.
- "Back on the Chain Gang" is one of the Pretenders' best-known songs, and makes a Shout-Out to Cooke's song in its chorus.
- "I'm Free from the Chain Gang Now" by Johnny Cash.
- The Crickets' "I Fought the Law" (later Covered Up by the Bobby Fuller Four, and still later by The Clash) has the singer "a-breakin' rocks in the hot sun", presumably as part of one of these.
- The video for AC/DC's "Jailbreak" features one.
- "Deliverance" by Bubba Sparxxx starts off this way.
- At one Venezuelan Theme Park, "La Venezuela de Antier" (Old-Timey Venezuela), all the cleaning employees are dressed as such, with the security employees wearing 1930's State Police uniforms.
- In SimCity 4, if you build the jail, chain gangs will show up on the streets in the vicinity of the building, performing manual labour with pickaxes on the roadside. Occasionally, one of them will try and make a run for it and has to be chased by the guards.
- The fourth case of Ace Attorney: Trials and Tribulations features Terry Fawles, who dresses like a chain gang member and even wears a ball and chain. Except nobody else in the game ever does this, so the odd implication is that he chose to dress up like that.
- The Powder Gangers in Fallout: New Vegas are former members of NCR chain gangs, and their founder is named Samuel Cooke. They were given dynamite to aid in mining, which is naturally also why they're all free now.
- In KZ Manager you must make your inmates work so that you could have the cash needed to gas them and cremate their bodies.
- In Planet Alcatraz, whenever you see railroads, you can see some prisoners working on them with pickaxes and sledgehammers. It's also implied to be the player's fate in one of the game over screens.
- The Simpsons episode "Kill The Alligator And Run" sees the entire family (yes, even Maggie) sentenced by the State of Florida to forced labor on a chain gang after Homer kills an alligator named "Captain Jack" (the Florida town's most famous resident) and addresses the jury at their trial as "Drunken Hicks."
- Lucky from King of the Hill has a grandfather who knew of a buried treasure in a forest that he found when he was an inmate working on a chain gang who was later sentenced to the electric chair, or, as Lucky put it, "A pastor" on a "church trip" who later "went on to be with the Lord."
- Even Mickey Mouse was on a chain gang, in the 1930 cartoon "The Chain Gang" (notable for being the first appearance of Pluto).
- The Adventures of Sonic the Hedgehog had a story where Sonic was sentenced to a chain gang with heavy characterizations of Southern US Prisons.
- Seen in the Flip The Frog short "Jail Bird."
- In the Family Guy episode "Holy Crap," Peter has kidnapped the Pope by posing as his driver and he drives the Pope Mobile past one of these. The Pope doesn't realize anything is wrong and keeps waving at everything, including a chain gang, parodying Cool Hand Luke:
Luke: (takes his shirt off) Taking it off there, boss.Guard: Taking it off there, Luke.Luke (wipes sweat off his face) Wiping it off there, bossGuard: Wiping it off there, Luke.Luke: (waves at the Pope) Waving at the Pope there, boss.Guard: Waving at the Pope there, Luke.
- In another episode, Peter and friends become a chain gang after being arrested by Corrupt Hicks in the South.
- Ren and Stimpy's job as pixies in "Pixie King" is more or less this, especially since they're whipped by policemen if they slack off for even a second.
Stimpy: Kissin' dew drops here, boss!
- Johnny Bravo had a parody of this in an episode where he is in prison. He is assigned to break rocks into little rocks, then glue the little rocks back into big rocks, and then break them back into little rocks. the last step was what drove him to madness.
- On CatDog, characters are seen breaking blocks of chlorine tabs for violating the rules at the public pool.
- On Rocko's Modern Life, Rocko's car is apparently part of one of these when he gets impounded. (And Prison Raped by a big purple truck.)
- In an episode of SpongeBob SquarePants, Mrs. Puff gets sent to prison, and works on one of these, while Patrick and Spongebob disguise themselves as rocks to try to help her break out. She doesn't want to be free (because she doesn't have to deal with Spongebob anymore), and the prison guards think she's insane.
- Happens to Daffy and Bugs in The Looney Tunes Show episode "Jailbird and Jailbunny".
- A flashback in the My Little Pony: Friendship Is Magic episode "The Crystal Empire, Part 1" shows the Crystal Ponies chained together in this manner during the reign of King Sombra.