|Played by||Dane Boedigheimer|
|Death||Gut wrenched, rotted away (revived), scared inside-out|
Pumpkin is a supporting character of The Annoying Orange. He was once a murder weapon because he killed Crabapple by being dropped on him. Pumpkin is first seen being brought into the kitchen and Orange mistaked him for his big brother. Pumpkin told Orange that he is actually a pumpkin and became annoyed when Orange repeatedly called him “Plumpkin”. Eventually, Pumpkin gets very frustrated by Orange and yelled at him to stop it. After Orange kept quiet, Pumpkin furiously told Orange about his relaxed personality, and corrected him. When Pumpkin asked him why is Orange mumbling his face, Orange then warned Pumpkin about Knife. Pumpkin was then attacked by Dane Boedigheimer, who ripped the top of his head off and pulled out his innards. Later, Orange is seen making fun of Pumpkin because Dane Boedigheimer had carved a face on Pumpkin’s buttocks to make him a jack-o-lantern, much to Pumpkin's anger. Pumpkin is later mentioned by Orange and Tomato, in which Orange tells Tomato that he is a vegetable like a pumpkin. Tomato says that pumpkins are fruits too even though they're not.Later, Orange annoys Crabapple by mentioning Pumpkin. Then, he accidentally killed Crabapple when he was dropped on him (with a warning from Orange). Pumpkin gets a warning of Crab, who then began to ride him like he did with the Golden Delicious apple. He has made many appearances since then in flashbacks. However, after a long absence, he makes a new appearance in Crappy Captioned 3: Plumpkin. He and Orange were reenacting Pumpkins debut using Google's automatic captions as a script. However, he was actually killed again when Orange frightened him so much so that he was actually turned inside-out.
- He is the first pumpkin in the series.
- He is the first character in the series to be revived.
- He is the first character in the series to have been mysteriously revived.
- He is the first character to die in a Crappy Captioned episode.