Harley

Harley is a Pokemon Coordinator from Slateport City who dresses like his lead Pokemon, Cacturne. He debuted in the episode "A Cacturne For The Worse", in which he and May participate in the Izabe Island Pokemon Contest. He becomes offended when she doesn't recognize Cacturne and later calls it "scary-looking". He offers her a cookie and she says it's "not half bad" and he takes it as an insult. He takes a photo of her and puts it in what can be assumed to be a "burn book" and draws a skull-and-crossbones over her photo. (In some airings of the episode, he draws a sad face.) He vows revenge on her for insulting his cooking and thus begins their rivalry.

Harley is very scheming and will use any means to defeat and/or humiliate his opponent. In "A Cacturne for the Worse" he tells May that Surskit is slow so she should let her Bulbasaur get in close before striking, almost costing her the win. He also records her little brother Max telling an embarrassing story about her and a group of Tentacool and plays it during the contest, effectively stressing her out until Ash tells her to calm down. He also allies himself with Team Rocket in the episodes "New Plot, Odd Lot" and "Going for Choke". In "Hi Ho Silver Wind" and "Deceit and Assist", he tells May to use her Skitty's Assist move in the next match, causing it to become confused.

Harley has lost most of his contests against May despite his cheating and deception, except for one, in "Harley Rides Again". He still manages to get plenty of ribbons from other contests and has enough to enter the Grand Festival, as he has won over ten contests.

Harley's gestures, expressions, and speech patterns tend to match those of a girl. He runs in typical anime schoolgirl fashion and his hips tend to shake when he walks. His outfit is very flamboyant, with tight bell-bottom pants and go-go boots. He also has silly nicknames for May and her friends, calling May "Miss Tent" and "Gingerbread Cookie" (in the Japanese, he calls her "Meno-chan" and "Kamo-chan") and Ash, Brock, and Max "May's boys" or her "boy toys". At one point in "Harley Rides Again" he calls Brock "big boy" and joins a crowd of girls in admiring Brock's Bonsly. In season 9 he began adding "honey" or "hun" to the end of his sentences when speaking to someone. For example: (to Contest MC) "Well, don't look at me, honey." He also uses several cliches in his speech ("Off to go powder my nose. Toodle-oo!"). In "Begin! Pokemon Contest- Grand Festival", he cross-dresses as May to stress her out before the contest begins, blowing a few kisses to Drew just to throw in a little jealousy factor. His appearance, actions, speech, cross dressing, and his rather blatant fanboying of James dressed as Norman in "Hi Ho Silver Wind" lead many to believe he is homosexual. Whatever the case may be, flamboyant is definitely the word to describe him.

History
Harley first competed against May in A Cacturne for the Worse!. When the two Coordinators met, Harley was annoyed at May for several petty reasons: she was not familiar with his Cacturne, she called Cacturne "scary," and she said the the cookies he offered her were "not half bad". Later, the two competed in a Contest, Harley using Cacturne and May using Bulbasaur. During the appeals round, he mentions that he doesn't want anyone to talk during their performance. After that round, in an attempt to publicly humiliate May, Harley played a recording of Max recalling a time when May was younger and she became stuck in water with a swarm of Tentacool and was extremely frightened. May was embarrassed, but went on to defeat Harley. Harley and May met up again in the episodes Hi Ho Silver Wind!, Deceit and Assist!, and Rhapsody in Drew!. Harley pretended that he was friends with May, and she initially believed him. He gave her "advice" to have her Skitty use its Assist move repeatedly to make a good appeal; this resulted in Skitty becoming confused after using Bulbasaur's Petal Dance, having to DoubleSlap itself out of confusion. Meanwhile, Drew watched Harley, noticing how he tricked May. Later, May realized Harley's ploy, and soon the two were to battle once again. This time, it was Harley's Cacturne and Banette versus May's Beautifly and Bulbasaur. May won this battle as well, and progressed further into the tournament. The next time May and Harley met was in Saffron City during the episodes The Saffron Con and A Hurdle for Squirtle. They met on this occasion in the Pokémon Center where Harley stated he was working as an assistant to Nurse Joy in gratitude for her healing his Cacturne. He stated that he was sorry and that he was working hard to make up for things. All of it was a lie and May nearly couldn’t compete because he "mistakenly" told her that she could use her Hoenn pass to compete. However, Lilian Meridian, the Kanto Contest MC, gave her a Kanto contest pass and ribbon box in thanks for her help in repelling Team Rocket when they raided the Pokémon Center. Harley competed in the contest using Cacturne for the appeals and Ariados for the battles. He defeated Jessie who entered with Wobbuffet, but was defeated himself by May and her Squirtle in the finals.

Harley's ribbons from Kanto The next time he appeared was in Harley Rides Again, where he competed in the Wisteria Town Contest, using Ariados in the appeals. He used Ariados's Spider Web to surround the stage with its web, similar to the previous contest. He then asked it to entangle itself with its web and use Scary Face, scaring everyone. He then used his Octillery against May's Munchlax in battle. After utilizing Octazooka, Sludge Bomb and Rest, he defeated May for the first and only time known so far. He appeared again in New Plot, Odd Lot! and Going for Choke!. This time after learning that May needed one more ribbon to enter the Grand Festival, he devised a plan to prevent this. To do this, he enlisted the help of Team Rocket, promising to help Jessie win and having James and Meowth help him sabotage May behind the scenes. However Ash, Brock, Max and Drew got wind of this and thwarted his plan.

Younger Harley In New Plot, Odd Lot!, it was also mentioned that part of Harley's hate for May came from when a girl who looked like May ate his food when he was younger. The next time was in May, We Harley Drew’d Ya!, Thinning the Hoard, and Channeling the Battle Zone, where he competed against May in the Kanto Grand Festival. In the Appeals Round, he used his Banette while dressed up as May, asking himself to be called Mayley. He used Cacturne and Wigglytuff against Munchlax and Eevee, but both defeated his Pokémon. The final major appearance he had was in The Unbeatable Lightness of Seeing where he simply watched May and Drew have a practice contest battle. At the end of the episode, he revealed that he was also going to compete in Contests in Johto. He also invited Jessie to do the same, but she denied, saying she still wanted to stay in Team Rocket. Because of this, he got mad at her. He then sent out his Cacturne to battle her. As she was searching for a Pokémon to use, Harley asked Cacturne to use Bullet Seed, sending Team Rocket flying with Jessie still looking for a Pokémon. He has Contest Passes to compete in Hoenn, Kanto, and presumably Johto as well. In A Full Course Tag Battle!, he and Wigglytuff appeared in a flashback. Then Harley, Solidad and Drew made a cameo appearance in Pruning a Passel of Pals!, watching May perform in the Wallace Cup. Harley tended to use nicknames for May behind her back. The first was Meno-chan (English equivalent: Miss Tent) after embarrassing her with the Tentacool story. The second was Kamo-chan, referring to the word often used at the end of May's sentences in Japanese that can imply unsureness. In English, he calls her various cutesy pet-names, including "gingerbread-cookie".

Pokémon
Harley seems to take immense pride in his Pokémon, so much so in fact that he dresses up in clothing modeled after his signature Pokémon, Cacturne. None of Harley's Pokémon share a particular type, but they all have one attribute in common: they can all be quite menacing in contests, even the normally cute Wigglytuff. This listing is of Harley's known Pokémon: