Friends’ Best Chandler Episodes: We Pick Some Of Matthew Perry’s Greatest Moments

Last Updated on November 2, 2023

With the passing of Matthew Perry breaking the hearts of Friends fans everywhere, tributes have begun pouring in online, with many noting how the always upbeat show was therapeutic to those going through rough times. I, for one, binged on the show during the pandemic. As the world shut-down around me, it was comforting to jump into a show I loved so much growing up. To my delight, the series worked (for me) just as well as it did twenty or so years ago. To pay tribute to Matthew Perry and his iconic portrayal of Chandler Bing, we here at JoBlo thought it would be a good idea to list our picks for the best Chandler episodes.

The One With The Blackout

To many, this is the first genuinely iconic Friends episode. It was the seventh episode of season one, and while the whole cast had good material to work with, it was Perry’s Chandler who emerged from the episode as a potential breakout. Chandler is separated from the rest of the gang, being trapped in an ATM vestibule with supermodel Jill Goodacre. Perry’s physical comedy prowess is on full display here, with him trying to impress Goodacre by nervously blowing a bubble. It also has one of his funniest lines when, after Goodacre offers him gum, he says, “that would be perfection,” only for him to immediately mock himself via voiceover for his bizarre choice of words.

The One Where Heckles Dies

This is another classic Chandler episode from early in season 2. When Larry Hankin’s curmudgeonly Heckles dies, he leaves all of his stuff to Monica (Courtney Cox) and Rachel (Jennifer Aniston), only for Chandler to become obsessed with how similar Heckles is to him in terms of his personality. This is especially true when he discovers Heckles’ Big Book of Grievances, detailing the various inane reasons he broke up with women he was dating. In desperation, he tries to reunite with his on-again/ off-again girlfriend Janice (OH MY GOD), only to discover she’s pregnant with another man’s child and has moved on (for now). While Perry is funny in this episode, he also infuses Chandler with a certain degree of poignancy that makes the character much more than the one-joke figure he might have been.

The One With All The Thanksgivings

While some complain about the show’s recurring fat-suit joke about Monica’s younger days, this is a terrific Chandler episode. Bing famously hates the holiday because that’s when he first learned his parents were getting divorced, leading to them all reminiscing about their worst Thanksgivings ever. This was the episode that sold me on Monica and Chandler as a couple, with her donning a turkey over her head (Mr Bean-style) to cheer him up on his most-hated holiday and act that makes him realize he actually loves Monica and vice versa.

The One With Chandler’s Dad

While this is controversial due to Kathleen Turner being cast as a female impersonator and how Chandler reacts to his father’s coming out, I think it’s a classic episode for the character. The thing is, Chandler isn’t perfect. He handles many things poorly, including his father’s lifestyle choice, but to me, that makes him all the more relatable. We all have sometimes handled things with less grace than we should have, and it’s nice to see the character reflect on his actions and grow from the experience. For me, that definitely makes this one of the best Chandler episodes.

The One With The Engagement Picture

In terms of pure physical comedy, it doesn’t get much better than Perry’s mugging as Chandler tries (and fails) to pose for an engagement photo with Monica. The rest of the episode is fine, but this comic setpiece is one of the show’s best.

What are your picks for the best Chandler episodes? Let us know in the comments!