The One Where Everybody Finds Out” (Season 5, Episode 14) – This episode is iconic for showcasing Chandler’s attempt to keep his relationship with Monica secret and the hilarious “They don’t know that we know they know we know” exchange.

“The One with All the Thanksgivings” (Season 5, Episode 8) – Chandler’s expressions and witty remarks as the group reminisces about their worst Thanksgivings make this a memorable episode. It’s also significant for Chandler telling Monica he loves her for the first time.

“The One with Ross’s Wedding: Part 2” (Season 4, Episode 24) – Although primarily focused on Ross’s wedding, Chandler’s banter with Monica culminates in the start of their romantic relationship, marking a vital development for his character.

“The One with the Blackout” (Season 1, Episode 7) – As one of the early showcases of Chandler’s sarcastic humor, him being trapped in an ATM vestibule with a supermodel is one of his finest moments from the show’s beginning.

“The One Where No One’s Ready” (Season 3, Episode 2) – Chandler’s spat with Joey over clothing leads to several hilarious moments, further solidifying his role as the comedic backbone of the series.

“The One with Chandler in a Box” (Season 4, Episode 8) – Chandler’s idea to punish himself by sitting in a box during Thanksgiving gives viewers a glimpse at his more sensitive and mature side.

“The One with Five Steaks and an Eggplant” (Season 2, Episode 5) – This episode features Chandler humorously dealing with an unintended case of identity theft after receiving someone else’s phone calls meant for “Bob.”

“The One Where Ross Got High” (Season 6, Episode 9) – While most remembered for Ross’s confession, it is Chandler’s relentless effort to win over Monica’s parents that brings the laughs in this Thanksgiving episode.

“The One with Monica’s Thunder” (Season 7, Episode 1) – Chandler’s support for Monica following their engagement showcases his character’s growth and their dynamic as a couple.

“The One Where Chandler Takes a Bath” (Season 8, Episode 13) – This episode highlights another facet of Chandler where he discovers and embraces the relaxation that comes with taking baths.

These episodes represent some of the best moments of Matthew Perry’s character on Friends, each highlighting his humor, vulnerabilities, and evolution over the show’s ten seasons.