For over ten seasons of thePokemonanime, Ash traveled across the regions of the first fourPokemongenerations with many companions. One consistent member of Ash’s traveling party was Brock, the Kanto region Gym Leader and aspiring Pokemon Doctor. However, Brock would be absent for Ash’s adventures in the Unova region.
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As Brock’s replacement, Unova Gym Leader Cilan joined the journey, who appears as part of a trio of Gym Leaders in Striaton City inPokemon Black & White. A self-proclaimed Connoisseur, Cilan is an expert on a variety of topics, making him a useful traveling companion for Ash. These ten episodes represent Cilan’s extraordinary work the best.
10Triple Leaders, Team Threats!
Cilan made his anime debut in the fifth episode ofPokemon the Series: Black & White. In the episode, Ash challengesCilan and his brothers, Chili and Cress, to his very first Gym Battle in the Unova region. Cilan happens to be the first of the three that Ash meets, welcoming Ash to Striaton City and leading him to the Striaton Gym.
There, Cilan reveals his identity as one of the three Gym Leaders. During their match, Ash mistakenly pits his Oshawott against Cilan’s Pansage, making their battle quite suspenseful. Ash doesn’t actually defeat Cilan until the subsequent episode,Dreams By The Yard Full, where Cilan officially joins Ash’s traveling party with Iris.

9Cilan Versus Trip, Ash Versus Georgia!
In the 40th episode of theBlack & Whiteseries,Ash competes in the Nimbasa Pokemon Battle Tournament, which began in the previous episode. The second episode of the tournament focuses on the two matches alluded to in the title: Cilan vs. Trip, Ash’s rival, and Ash vs. Georga, Iris' rival. Cilan’s battle with Trip takes up the majority of this episode.
Cilan enters his match with Trip with a courteous attitude, but Trip is focused on winning. Cilan pits his Dwebble against Trip’s Gurdurr, as Cilan expertly analyzes Trip’s battle style, to the annoyance of Iris. Cilan’s Dwebble finally manages to knock out Gurdurr, eliminating Trip from the tournament and advancing Cilan ahead, matching him up against Luke.

8The Strongest Duo! Clemont and Cilan!
Long after Cilan departed from Ash’s journey at the end ofPokemon the Series: Black & White, he returned in a special episode that takes place after the subsequent series,X & Y. Here, Cilan crosses paths with Clemont, the Lumiose City Gym Leader and Ash’s traveling companion in that series. Together, they make quite a knowledgeable duo.
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The two meet when Cilan observes Clemont’s electronic fishing rod, criticizing it for lacking the thrill of fishing. Cilan spends the day exploring Lumiose City with Clemont and his little sister, Bonnie, before parting ways to explore the Tower of Mastery in Shalour City. However, the two first combine forces to rescue Bonnie from a faulty subway system.
7Cilan and the Case of the Purrloin Witness!
Often, Cilan’s adventures with Ash would lead for opportunities for him to flex his various skills. One of these is his detective skills, which he brings out to investigate mysteries around the Unova region. In this episode, however, Cilan must confront his fear of Purrloin to locate the thief of the Eye of Liepard, belonging to the gem collector Mrs. Ripple.
When Cilan deduces that Purrloin witnesses the thievery take place, the Dark-type Pokemon becomes integral to uncovering the perpetrator as Teaque, who used his Vanillite to carry out the crime. With their side-adventure over, Ash wonders if the experience cured Cilan’s phobia, but Cilan believes it hasn’t, yet hesitates to reveal the reasoning for his fear.

6A Connoisseur’s Revenge!
Cilan’s Connoisseurship is a major part of his character, for both practical and comedic purposes. His expertise in various subjects makes him handy to have around for certain episodes, especially during mysteries like the previous entry. However, his Connoisseur status isn’t revealed until the 19th episode of the series.
Upon visiting a shop for Connoisseurs, Cilan runs into an old challenger, Burgundy, who happens to be a child. Burgundy demands a rematch, sending her Dewott and Sawsbuck out against Cilan’s Dwebble and Pansage. Cilan eventually wins, but not before betting Ash changing his entire Pokemon party if he were to have lost.

5Clash of the Connoisseurs!
Burgundy eventually returns in episode 80, which finds Cilan and his traveling companions invited by Mr. Hatterly to help pick out his daughter’s first Pokemon. However, Cilan is hired alongside Richard Nouveau, another A-class Connoisseur. The two butt heads over their choices, with Richard preferring Petilil, while Cilan thinks a dual-type Pokemon is best.
Related:Pokemon: Best Dawn Episodes, Ranked
The two end up having a Pokemon battle to determine whose advice Mr. Hatterly will take. Cilan is thrown, however, by Richard’s chosen Pokemon: a Purrloin. Nevertheless, Cilan sends out his Crustle, besting Richard with a type-advantage, and simultaneously thwarting Burgundy’s interruption. Having won, Cilan recommends Foongus for Hatterly’s daughter.
4Cilan Takes Flight!
In the 67th episode ofPokemon the Series: Black & White, Ash and his companions make it to Mistralton City. There, Ash plans to challenge the city’s Gym Leader, Skyla, but Cilan is put-off by her method of enacting battles. Rather than actually face her opponents,Skyla analyzes the potential outcomes in her mindand determines a winner.
Cilan, feeling this is unfair as a fellow Gym Leader, challenges Skyla to a real Pokemon battle. However, Cilan’s attempt to prove her method wrong fails, and Skyla actually does win the battle, just as she predicted. Though Cilan takes the loss pretty hard, it only strengthens Ash’s determination to beat her in a real battle during the next episode.

3A Call For Brotherly Love!
In this episode, Cilan reunites withhis brother and fellow Gym Leader, Chili. Upon reuniting, Chili challenges Cilan to a battle, which he loses despite having a type advantage. Cilan later learns from his third brother, Cress, that Chili has been on a losing streak, but ever the supportive brother, Cilan decides to analyze Chili’s battle strategy and help him win.
Cilan deduces that Chili’s Pansear needs a non-Fire type move for balance. After teaching it Solar Beam to counter Pansear’s weakness to Water-type Pokemon, Chili challenges Ash to a battle. Chili regains his confidence after Pansear overpowers Ash’s Oshawott with a tide-turning Solar Beam, then parts ways with Cilan and his traveling companions.

2A UFO For Elgyem!
One of the more unique episodes inPokemon the Series: Black & Whitefinds Ash and his friends encountering a UFO. As it turns out, the flying saucer belongs to Professor Icarus, who studies outer space. Shortly after meeting the professor, Ash, Cilan, and Iris encounter Elgyem,a Psychic-type Pokemon that’s said to be from another planet.
This episode is a great opportunity for Cilan to flex his knowledge on space, something he’s learned from reading Icarus' work. Cilan’s space expertise ends up becoming useful as Ash and his friends attempt to rescue Elgyem from the clutches of none other than Team Rocket. Cilan plays a major role in using his Pansage to free Elgyem from his trap.

1Cilan and Brock! Gyarados’s Imperial Rage!
Clemont’s meeting with Cilan in theX & Yspecial harkens back to another special episode that occurs atthe end ofPokemon the Series: Black & White. After parting ways with Ash, Cilan meets Brock in Johto when heading to a Pokemon Center to treat his Pansage. The two eventually team up with Officer Jenny and Nurse Joy to temper an angry Gyarados.
While Pansage lulls Gyarados to sleep, Brock climbs it and uses a Super Potion on a wound that was irritating it. Sadly, Cilan and Brock never learn each others' identity, or the fact that they shared a traveling companion. Their teamwork will make anyPokemonanime fan wish they had more time to adventure together.


