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Jail-Broken is the first episode of season 2 of The Cuphead Show! and is the thirteenth overall.


Cuphead and Mugman are in the slammer after breaking into the cookie factory. Prison's scary -- but now they can't decide whether to bust out or stay in.


The setting of the episode is in a jail. Cuphead and Mugman are in jail after the break-in in the episode "In Charm's Way". After being scared by Miss Cyclops, Cuphead then proclaims that they are going to break out of jail at midnight. They break out, but get caught three times before Mugman gives up. Mugman says he's going to make the best of it and serve his time. However, Cuphead says "the only way we'll get outta here is if we break out." The two get into an argument.

After what seems like a few days, Cuphead has come up with a plan to break out. Mugman decided to sit it out. Cuphead digs a hole out his cell and digs his way to the electric chair room. He gets electrocuted and makes his way back to his cell, with Mugman laying in bed. Cuphead gives up trying to break out, but Mugman has a better idea to break out.

This time, Cuphead and Mugman break out with the laundry service that comes every night. Miss Cyclops is also there, and she tells Mugman through grunts that she'll miss the way he cleans her blanket. However, Mugman and Cuphead get caught again, but Miss Cyclops is there to save them with her lock-up chain. They return home where Elder Kettle tells them that he met Ms. Chalice and that the boys are grounded. They thank Elder Kettle for grounding them and kisses his feet, leaving Elder Kettle understandably confused.

Cast of Episode[]



  • Miss Cyclops, who appears in the prison in this episode, bears a resemblance to the Cyclops that appeared in Rugged Ridge and may be based off him; however, the Rugged Ridge cyclops is much larger than her, and she wears a prison outfit primarily due to the fact that she is in jail while he tends to go naked.
  • Mugman has made about 43 markings on the wall, which could mean he and Cuphead have been in jail for over a month. Yet again, he has most likely written this much due to his downhearted state. Additionally, it is mentioned in the last episode of the season that a month has indeed passed (since the first episode) but after they're out of jail, making the latter argument more accurate, and confirming that they have been in jail for at least a few days.


  • In a scene where Cuphead screams, he becomes small for one frame.


The Cuphead Show! Episodes
Season 1
Carn-EvilBaby BottleRibby and CroaksHandle with Care!Roll the DiceGhosts Ain't Real!
Root PackedSweater Off DeadSweater Luck Next TimeDangerous MugmanDirt NapIn Charm's Way
Season 2
Jail-BrokenCharmed & DangerousA High Seas Adventure!Another BrotherSweet Temptation
The I Scream ManPiano LessonRelease the Demons!Dead BrokeRats All, FolksSay Cheese!
Lost in the WoodsThe Devil's Pitchfork
Season 3
The Devil's Revenge!Don't Answer the DoorCupstagedRoadkillHoliday Tree-ditionA Very Devil ChristmasSpecial DeliveryDown & OutJoyrideDance with DangerThe Devil & Ms. Chalice