Ash's Charizard/History/Original Series/Orange Islands

Ash took Charizard with him to the Orange Islands, despite its refusal to obey him. Ash had noticeably stopped trying to use it in battles, although in the episode Navel Maneuvers, Charizard, Pikachu, and Bulbasaur were used in the second round of the match between Ash and Danny. Charizard was initially unwilling to participate, and Danny nearly won. However, Charizard inadvertently helped when it tried to use Flamethrower on Ash but missed and carved an ice pillar into a sled. This meant Ash won the round and was able to continue the match.

In A Way Off Day Off, although it did not obey Ash, Charizard recognized the wisdom and formidable experience that Tracey's Scyther had, and the two teamed up to defeat Team Rocket. Scyther was the only Pokémon in the group whom Charizard respected.

Charizard continued to ignore Ash during battles, such as in The Mandarin Island Miss Match. Charizard took down a boy's with a single attack, before flying away and rampaging the city. Ash was unable to recall it and only the intervention of Prima and her using  allowed Ash to stop Charizard. In Charizard Chills, Charizard battled Tad's. It blatantly refused to listen to Ash's commands, continuing to use Flamethrower despite it having no effect on Poliwrath. Tad and Poliwrath resisted all of them until Poliwrath responded with a Water Gun that nearly doused the flame on Charizard's tail. It was then encased in ice by Poliwrath's, much to Ash's horror. Ash managed to smash the ice encasing Charizard's head, and Tad walked away scornfully, telling Ash that they would have a rematch when he could control Charizard. Ash lit a fire and thawed Charizard out, before rubbing Charizard all over to help it regain its body heat. Pikachu pointed out that Ash's hands were rubbed raw, but Ash replied that he didn't mind, and redoubled his efforts upon seeing that Charizard's flame was so small. Charizard woke up in a panic and tried to attack, but it was so cold that it could not produce a flame and passed out again. Misty provided a blanket and Tracey kept the fires up while Pikachu watched the flame, but Ash himself worked throughout the entire night to help Charizard recover.

The selfless act reminded Charizard of everything Ash had done for it since it was a Charmander. By morning, Charizard's respect and loyalty to Ash had returned, and it helped Ash rescue Pikachu from Team Rocket. Ash and Pikachu were briefly knocked out during the rescue, and Charizard became so incensed it learned Dragon Rage. In a rematch with Tad and Poliwrath, Charizard learned to dodge Ice Beam and knocked Poliwrath into the air before defeating it with Seismic Toss.

It participated in Ash's Gym battle against Luana in Double Trouble. It fought Luana's and  alongside Ash's Pikachu in the series' first official Double Battle. The two Pokémon initially had trouble collaborating, but eventually managed to work together: Pikachu helped to free Charizard from Alakazam's attack and Charizard caught Pikachu after it was hit by Marowak's  attack. Charizard's skillful flying caused Marowak and Alakazam to knock each other out, earning Ash the Jade Star Badge.

Charizard was also used in Ash's Orange League battle against in Enter the Dragonite. Charizard defeated Drake's by blocking its electricity with Fire Spin and knocking it out with Seismic Toss. It also fought, but was hit by a powerful and then med into the ground. After a clash of Dragon Rages, Charizard fainted, but its attacks had begun to wear Dragonite down, paving the way for Pikachu to finish it off and give Ash the victory. Charizard was inducted into the Orange Islands Hall of Fame with Ash's other Pokémon.