The episode starts off with Jake sitting in the boat at the top of the Tree Fort and saying how the male birds are so much nicer than the females and the females are all plain. A bird flies up to him and tells him that the female birds are beautiful on the inside. He says he has a special delivery for Jake, it is a tape that says "URGENT. Watch now."
Jake goes into the tree house, and gets BMO to play the tape. He sees a person being held hostage and wonders what he is watching. The bag is taken off the person's head, and Jake Jr. struggles to try to get free. Jake gasps and becomes enraged. The mystery man tells Jake that they knows about Jake's criminal past, and that he has to get his old gang back together to steal the purest form of sugar: the Baker's Shard.
Jake changes his appearance into a more sinister one. He tells BMO not to tell Finn about what he is doing. Then, he presses a button which alerts all of the members of his old gang - Tiffany, the Flying Lettuce Brothers and Gareth - it is time for them to have a meeting.
The members gather, and Jake tells them what the situation is. Tiffany expresses the will to battle Finn, but Jake tells him not to get him in the mess, leading to a scene where Finn is randomly playing instruments and talking to BMO. The gang members are having a fight, with the others thinking Jake has gone soft. After Jake says that his daughter is kidnapped and he has to save her, they agree to go along with the plan.
At the Candy Kingdom, the Captain Banana Guard and the Private Banana Guard are awaiting their shipment of milk. Disguised as milkmen, Gareth and the Flying Lettuce Brothers enter their room and put the captain to sleep. Mimicking the captain's voice, the Flying Lettuce Brothers force the Banana Guards to go outside and shout as loud as they can, so they won't hear the bomb exploding the vault containing the Baker's shard.
Knowing the place well, Tiffany tells Jake how to get to the Baker's Shard. After avoiding a series of traps, Jake reaches the Baker's Shard. On the other side of the hall, he hears the voice of his daughter's kidnapper. Throwing to him the Baker's Shard, it is revealed as the voice from Flying Lettuce Brothers, who have been using a different voice. After the gang members reveal themselves, Tiffany sets off the alarm so that Jake would get caught.
Angered because his gang tricked him, Jake grows extremely large, chasing the milk van they came with. After finally catching, Jake finds out that the van was driven by Jake Jr. herself. After the gang runs away, Jake Jr. reveals she heard stories from her mother about Jake's criminal days. This gave her an inspiration to trick her dad and make him proud. Jake tells her that what he did was wrong and he is not doing it anymore. The episode ends with Jake and Jake Jr. walking into the sun, heading for the Tree Fort.
- Mail Bird
- Banana Guards
- Lollipop Girl
- Kenneth (in BMO's Screen)
- Ice Cream Lady (in BMO's Screen)
- Squeez-E-Mart boss
- This is the first time a post-war vehicle is seen to fully function unlike the candy helicopters in "Princess Cookie."
- It is revealed that banana is the forbidden milk flavor for Banana Guards, since it may be interpreted by the Banana Guards as drinking their own kind's blood.
- Jake Jr. is already 22 years old during this episode.
- Lollipop Girl is voiced by Maria Bamford instead of Niki Yang in this episode.
- This episode also marks the first time Lollipop Girl has multiple lines of dialogue, rather than just singing or having one line of dialogue.
- In the animatic shown at Wondercon, at the Squeezy Mart, Rick Astley's Never Gonna Give You Up, better known as "Rickroll" due to its involvement in one of the most famous internet memes of all time, can be heard. This however did not appear in the actual episode.
- In the film Fast Five, there was one line from Dominic Toretto to Brian "We're gonna use this, do one last job... and disappear, forever." The episode involves a similar "criminal past" (Dominic has escaped prison twice) and pulling off a job with the help of "a team," to steal the vault of Reyes' money.
- The Milk Van that Jake and the gang used is a 1959 Isuzu Elf TL151 Van.
- There's a simultaneous reference when Tiffany speaks in the vault inside Jake: there's a reference to "The Charge Of The Light Brigade" ("the jaws of death") and "The Four Horsemen" ("pale horse")
- The sign next to the button that Jake pushes reads キュウ ▪ いそ.ぐ いそ.ぎ, the readings for the kanji 急, meaning 'hurry,' 'emergency,' 'sudden' and 'steep.'
- The corridor scene makes a reference to Super Mario Bros., specifically the castle levels, with a 2D platforming-type perspective and Jake being chased by fireballs spat at various heights.
- When chasing down his escaping cohorts, Jake assumes the form of an animal somewhat resembling the Cat-Bus of My Neighbor Totoro.
- The mugshot of the Flying Lettuce Brothers, shown during Jake Jr.'s fake blackmail video, features their names "F.L.Bros" as well as their prisoner code "12XU" a reference to the song of the same title written by British post-punk band Wire and later covered by American hardcore band Minor Threat. (It should be noted the Flying Lettuce Brothers is also a reference to the 60's American rock group The Flying Burrito Brothers.)
- In Regular Show, there is a character (Garret Bobby Ferguson from the episode "High Score") that bears a striking resemblance to Gareth having a giant head also, and in addition his name (Garett) sounds a lot like Gareth.
- Tiffany makes his first actual appearance since "My Two Favorite People."
- Jake puts the tape in BMO's butt like in the episode "Holly Jolly Secrets Part I."
- Jake wears his milk man costume again as seen in "Princess Cookie."
- The Squeez-E-Mart makes a real-life appearance instead of just being in a flashback in "Ghost Princess."
- Lollipop Girl speaks with an American accent rather than a French accent.
- This episode was aired in Canada on May 6, 2013, instead of "James Baxter the Horse."
- According to Jesse Moynihan, Gareth and Flying L. Bros were not always planned to be Jake's criminal buddies. They used the names from the phone because they thought it would be a nice detail to make a reference to an earlier episode.
- It is possible that Tiffany is dyslexic. If one is to look closely at his arm during his first poem, everything is spelled correctly, but in his second poem about Jake near the end of the episode the poem reads: "Now I'm the Dob, and you're the Yail, now you chase me, chase my [indistinct letter]reams!" although the misspelling could also be due to having more street smarts than book smarts.