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Gary's cheerleaders (Japanese: シゲル応援ギャル Shigeru's cheering gals) were a group of girls, also considered friends, that traveled with Gary during his Pokémon journey. Six of them helped cheer Gary on, much like real-life cheerleaders at sporting events, while a silent seventh member of the entourage chauffeured the group around in a red convertible car.
They debuted in the first episode, where they were seen outside Professor Oak's Laboratory cheering for Gary as he received his starter. Their motto is:
- "Gary, Gary, he's our man. If he can't do it, no one can! Go...Gary!".
The entourage continued to appear alongside Gary; and therefore were seen in Beauty and the Beach, Dig Those Diglett!, Attack of the Prehistoric Pokémon, and Riddle Me This.
His cheerleaders watched Gary challenge Giovanni to a Gym battle in The Battle of the Badge. However, they were frightened and later upset when Gary lost to Mewtwo. Later, they watched Ash take on the Team Rocket trio, who served as temporary Gym Leaders while Giovanni had an unrelated business to attend to. Ash went on to earn himself the Earth Badge, despite the trio's attempts to cheat, and Gary's cheerleaders cheered for him:
- "He's our winner, he's our Ash! Let's all have a victory bash! He's our winner, he's our man! No one wins like Ketchum can!".
Afterwards, the cheerleaders supported Gary throughout his Indigo Plateau Conference campaign beginning in All Fired Up!. The group was left distraught after Gary's loss to Melissa in The Fourth Round Rumble, and they all left the Indigo Plateau with Gary soon after.
The cheerleaders were then absent for most of the Johto League. They finally reappeared in The Ties that Bind and Can't Beat the Heat!, where they supported Gary as he competed against Ash in a Full Battle round during the Silver Conference. Unlike the previous battles, they did not start crying when Gary lost to Ash. The cheerleaders haven't been seen since Gary decided to become a Pokémon Researcher like his grandfather.
Gary's cheerleaders are a lively group with exuberant personalities. They enjoy a life of luxury, like in Riddle Me This, where they took a holiday in a private Cinnabar Island hotel suite with Gary prior to the Indigo Plateau Conference.
Their beauty and incredible support for Gary often made Ash jealous. Conversely, their rhyming slogans and pep bolstered Gary's own confidence, which also helped inflame his ego during his Pokémon journey. The girls were shown to cry whenever Gary lost a challenge, like in The Battle of the Badge and The Fourth Round Rumble.