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Lord Cholmondeley first appears in the episode "Prime Target" in season 2 of Generation 1. He captures a secret Soviet jet, taking the world to the brink of World War III, when the Soviets accuse the United States of capturing it. He then decides he wants to capture the ultimate trophy, the head of Autobot leader, Optimus Prime.
First he captures several Autobots (Tracks, Bumblebee, Jazz, Beachcomber, Grapple, Blaster and Inferno), and invites Prime to come and rescue them. Holding the Autobots in a bizarre torture chamber, Prime is forced to battle Cholmondeley's robotic creations to reach them.
Megatron dispatches the Decepticon Triple Changers Astrotrain and Blitzwing to make an alliance with Lord Cholmondeley; however, he also captures them when Astrotrain interferes and blasts Optimus Prime.
Prime later reaches Cholmondeley's lair, where a panicked Cholmondeley offers to free Astrotrain and Blitzwing if they fight Prime. They agree but doublecross him, and chase him instead, allowing Prime to free the Autobots. Cholmondeley is later delivered to the Soviets tied to the jet he stole at the beginning of the episode.
In Transformers: Rescue Bots, Lord Chumley bears the first name of Thurston and is the brother of an original Rescue Bots villain, Colonel Quint Quarry. Thurston and Quint were raised in a family that believed in catch and release animal hunting, and that cared for a lion that was abandoned as a cub due to being cross-eyed. The lion was later given to the Griffin Rock zoo, but Thurston departed from his family's traditions and began imprisoning animals for his own enjoyment, changing his name to distance himself from his relatives. He had a great deal of success, even adding creatures that were thought to be extinct to his collection and keeping all of his acquisitions in prison. A rivalry also developed between him and his brother, and after Quint was imprisoned by the Burns family Chumley seized his Helijet and Q-Drones for his own use.
Chumley eventually drew his brother's foes onto his trail after he abducted the cross-eyed lion, now named Whiskers, from the Griffin Rock Zoo. After learning of Chumley's existence-though not his heritage-from his brother, the Burns family set a trap by having their partners, the Rescue Bots, adopt Dinobot form and having Quarry pass a message to Chumley. However, Chumley proved more cunning than anticipated and seized the Rescue Bots after freeing a number of other animals in the zoo to cause confusion. He then had the Rescue Bots brought to his ship, where he briefly imprisoned them before being found by the Burnses, who soon released their partners and several of Chumley's captive animals. To escape their wrath, Chumley sealed himself in one of his own stasis tubes, and was delivered to the authorities while his animals were given a safe new home; Quarry subsequently reclaimed his technology and revealed their relationship to Cody Burns.