In the Advanced Generations series, Ash appeared with new clothing - a black and red hat with a green Poké Ball on it, a blue sleeveless hoodie with gold trim and white hood, a black short-sleeve undershirt with a red stripe, black fingerless gloves with light green borders, light blue jeans with knee stitchings, and blue sneakers.
Since entering the Hoenn region Ash became a mentor to a new trainer name May, much like how Misty and Brock were to him. Ash started to train with his Pokémon more than he previous did, along with him doing practice battles with his friends to help with their Pokémon's moves. Ash is a little more of taking his rivals more serious as Gary moved on to become a researcher. Also, he's getting better at opening up to advice and being patient with others. Ash is beginning to understand that his hotheadedness needed fixing, especially when it came to battling, but still kept it when Pokémon were being mistreated while keeping some of his other traits and love for Pokémon.
Pokémon the Series: Gold and Silver
Starting a new journey, Ash received new clothes from his mom, trading his familiar button-up shirt for a sleeveless hoodie, his green gloves for black ones and got a new cap. Breaking with what he'd done previously when he left for Johto, Ash left the rest of his team with Professor Oak and Tracey, intent on capturing new Pokémon in Hoenn, taking only Pikachu, his Starter, with him from home - the idea being to recapture the feeling of first leaving Pallet Town as a new Trainer.
Ruby and Sapphire
Upon arrival, he gained two new traveling companions in May, a beginner Trainer starting out on her journey with no clue what to do, and her younger brother Max, who has an extensive, impressive knowledge of Pokémon that far exceeds his years. Brock also returned, having finished his errands at home in Pewter City. Ash won his first three badges by the end of the season: the Stone Badge from Roxanne of the Rustboro Gym, the Knuckle Badge from a rematch with Brawly from the Dewford Gym, and the Dynamo Badge from Wattson of the Mauville Gym. He also caught three Pokémon: Taillow, Treecko and Corphish.
Pokémon the Series: Ruby and Sapphire
Ash was eager to challenge more Gyms, but was held up by May as she decided to be a Pokémon Coordinator. Ash encountered both Team Magma and Team Aqua, two villainous crime syndicates occupying the Hoenn region for the first time. Ash also won the Heat Badge from Flannery, the Balance Badge from Norman, May and Max's father, and a Feather Badge from Winona. Ash's Pokémon team changed a bit. He caught a Torkoal while his Treecko and Taillow evolves into Grovyle and Swellow.
Before winning his last few badges, Ash was caught in a clash between Teams Magma and Aqua as they unleashed theLegendary Pokémon Groudon and Kyogre to reshape the world. Due to Pikachu's connection with Groudon, both teams were stopped and the legendary Pokémon returned to rest. After that, Ash beat the twin Gym Leaders Tate and Liza for the Mind Badge and Grand Festival winner Juan for the Rain Badge. Prior to entering the Hoenn League, Ash declined an offer from Professor Oak to trade in his current Pokémon with his previous captures on the grounds that his new team had earned it for themselves. He gained two new rivals in Morrison and Tyson, the former he would beat, but the latter he would lose to. He placed among the Top 8. He caught a Snorunt, which later evolves into Glalie.
Returning to Kanto with Brock, May and Max, Ash was invited to partake in the Battle Frontier, battling Frontier Brains for Frontier Symbols. Upon encountering the first Frontier Brain, Factory Head Noland and his Articuno, Ash left his friends for a quick bit while the Factory Head took Max and Pikachu up in his airplane, telling them "I had to make a phone call." Later that night, as the gang was watching Noland's Pokémon eat dinner, they speculated which of Noland's Pokémon Ash would challenge: Max guessed Venusaur, May guessed Rhyhorn, but Ash, aiming high, boldly decided on Articuno, the Legendary Bird of Ice. Wondering which of Ash's Pokémon he would use against a Legendary, the gang was excited when they saw his pick; Ash had gone straight to the top and brought in the big guns, calling in Charizard from the Charicific Valley to take on the Ice/Flying-type head-to-head. Despite the Type advantage being set against it, Noland's Articuno demonstrated its ability to quickly recover after taking direct hits from Charizard's Flamethrower and DragonBreath attacks and managed to gain an advantage over the fiery behemoth with an Ice Beam to the wingtip and repeatedly combining its Ice Beam and Water Pulse attacks, the latter move being strong enough to counter Charizard's newest move: Overheat. Ultimately though, Charizard managed to withstand Articuno's Steel Wing attack, and as the Legendary Bird came in for one last strike, it grabbed its wings in midair, stopping the attack before it could connect and topped it off with its signature Seismic Toss, knocking out Articuno for the win and earning Ash the Knowledge Symbol.
Ash battled all of the remaining Frontier Brains, Arena Tycoon Greta, Dome Ace Tucker, Pike Queen Lucy, Palace Maven Spenser and Salon Maiden Anabel, and earned their Frontier Symbols. The last Frontier Brain however, Pyramid King Brandon, proved to be more difficult for Ash to defeat; Their first official battle saw Brandon's Registeel defeating Ash's Torkoal in spite of a new move it learned. For their rematch, which would be four-on-four, Ash took a "back to your roots" approach, once again calling in Charizard but also this time bringing in Bulbasaur and Squirtle to reunite his trio of Kanto Starters. Putting them together with Pikachu, Ash formed a team of aces from his early days: pitting the four aces against Brandon's Dusclops, Ninjask, Solrock and Regice, he finally claimed victory and the final Frontier Symbol - the Brave Symbol - completing the set and winning the Battle Frontier. After his victory, Scott offered Ash the position of Frontier Brain when one of them retired but he declined, opting instead to continue his journey. Before saying goodbye to May, Ash competed against her in the Terratta Pokémon Contest, their match ending in a tie. There was only one ribbon and they couldn't decide who to give it to. Ash had his Sceptile use Leaf Blade to cut the ribbon in half, choosing to split it with May before they all parted ways. Returning home, Ash met up with Gary again and saw the latter's new Electivire. Gary informed Ash about the region of Sinnoh, to which he immediately decided to travel next on his journey. He manages to catch an Aipom.
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