The Pumpkins are pumpkins that have been possessed by spirits that serve Jack O'Lantern and have a similar sense of humor. They usually always appear alongside Jack.
Jack brought them to life with the Reaper's scythe by opening a portal to the Underworld while standing in a large pumpkin patch, and having the spirits that came through the portal posess the pumpkins. The spirits possessed and seemingly mutated the pumpkins into various shapes and sizes. The pumpkins then proceeded to cause chaos throughout Endsville, with Jack riding on top of the largest one.
They were destroyed after laughing to death at Irwin.
The Pumpkin to the left is merely based on pumpkin shaped Halloween buckets and are not made of actual pumpkin, nor do they live. The Pumpkin on the right is an actual pumpkin, and does, in fact, live.
Ironically, it also says they hate Fall holidays (due to being cooked into Pumpkin Pie, and being hollowed out for jack-o-lanterns), which makes their aiding Jack in making it Halloween every day a questionable decision
Maxwell Atoms later reused both the concept of monster pumpkins and some of the pumpkin designs in Happy Halloween, Scooby-Doo!. The main antagonist is a glowing eyed, large mouthed, quadrupedal pumpkin, who eats people.
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