"Chipwrecked" is the second segment of the fiftieth episode of Big City Greens and it serves as the second of two mid-season finales.
Cricket invites the family to "bring your family to work day" and has Bill, Tilly and Gramma Alice perform "activities" for him. Gloria calls out Cricket as he is clearly just trying to get them to do his work for him, but Cricket says that Ms. Cho does not mind as they are working for free. A plant watches Cricket who is wearing cameras on him; feeding directly to Wholesome Foods CEO Chip Whistler who is still trying to get his revenge on Cricket and the Greens. Chip admits to his subordinates that his previous attempts at trying to outwit the Greens have all ended in failure, mostly due to inappropriately handled billboards that keep falling and crushing him, and once again announces that his next plot will not fail this time. Chip's VP Chairwoman enters and tells him that he needs to run the company instead of focusing his attention on the Greens, but Chip refuses and enacts his plan.
As Gloria once again complains to Ms. Cho about Cricket's behavior, Chip arrives in a truck to promote Wholesome Coffee in an effort to run Big Coffee out of business. The Greens and Gloria all point out that they no longer take him seriously despite his supposedly guaranteed solution to defeating them. Officer Keys arrives to tell Chip that his truck will be towed because he parked next to a fire hydrant. Chip attempts to stop this, but is comically fired into the air by the hydrant and snowballs until he is crushed by another billboard, chipping his tooth once again. Cricket mocks him for his failure as Chip returns home sad and defeated. His father calls him who, unaware of his vendetta, gives him encouragement and tells him to use the company to aid him. Inspired by his words, he fires his Wholesome employees.
Chip comes to his meeting prepared this time and asserts his dominance in the company offering an idea for expansion. Back at Big Coffee, the Greens catch on to Cricket's scheme and he apologizes for using them to help in getting out of work. Chip enters the store and sends in able bodied men to tear the interior apart. Gloria and Ms. Cho arrive demanding to know what is happening and Chip offers Ms. Cho a large check, causing her to smile and speak, as she happily goes on vacation. Chip fires Cricket and Gloria and kicks everyone out of Big Coffee. He announces his plan to not only rebrand the cafe, but also "expand" onto the Greens' property. As he sarcastically thanks Cricket for his "advice", Gloria and the Greens are left devastated as the words "To Be Continued..." flash onscreen.
- Chris Houghton as Cricket Green
- Marieve Herington as Tilly Green
- Bob Joles as Bill Green
- Artemis Pebdani as Gramma Alice
- Anna Akana as Gloria Sato/Miriam Cho
- Andy Daly as Officer Keys
- Shane Houghton as Wholesome Greg
- Mary Holland as Chairwoman
- Paul Scheer as Chip Whistler
- Ed Begley Jr. as Mr. Whistler
- The title shares its name with the third live action Alvin and the Chipmunks movie Alvin and the Chipmunks: Chipwrecked, as well as an episode of Chip 'n Dale Rescue Rangers, "Chipwrecked Shipmunks".
- Ironically, the usual Green family plot is playing in the background as Chip Whistler is the main focus.
- Nobody takes Chip seriously until the end of the episode.
- Nancy Green, Remy Remington and Phoenix are seen as photos, but do not physically appear in the episode. Apparently, Chip does not know Remy's name, nor his significance to Cricket.
- Chip has apparently had numerous other schemes that have all failed in one form or another
- One of his schemes references the famous Wile E. Coyote and Road Runner brand of Looney Tunes shorts where Chip paints a tunnel, only for Tilly to go through it and Chip failing to do so. The Road Runner's famous "Beep Beep" is even used.
- Ms. Cho speaks for the first time uttering "Peace out, my dudes!"
- Anna Akana and Shane Houghton are finally credited for voicing Ms. Cho and Wholesome Greg. Prior, their voices are never credited or are listed as Additional Voices.
- The end credits depict Big Coffee boarded with up with a sign saying "Out of Business" and ominous music playing. This continues the trend of other Disney Television shows where the end credits become ominous or change tune depending on a serious event happening such as in Star vs. the Forces of Evil with "Starcrushed", The Owl House with "Agony of a Witch", Tangled: The Series with "Queen for a Day", "Cassandra's Revenge" and "Once a Handmaiden..." and Gravity Falls with "Dreamscaperers" and "Dipper and Mabel vs. the Future".
- Sometimes your enemies can actually succeed with their plans.
- Don't scam your family.