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The Best of Chandler Bing: Top 10 Matthew Perry 'Friends' episodes we can't stop binge-watching

The hit sitcom 'Friends' chronicles the lives of six friends staying in New York while struggling to balance their career, family and friendships
UPDATED MAY 28, 2024
Let's take a peek into the best 'Friends' episodes of the King of Sarcasm Chandaler Bing, played by late Matthew Perry (@nbc)
Let's take a peek into the best 'Friends' episodes of the King of Sarcasm Chandaler Bing, played by late Matthew Perry (@nbc)

LOS ANGELES, CALIFORNIA: Those were the glorious days when the late Matthew Perry embodied the charisma and charm of Chandler Bing in the hit sitcom 'Friends' illuminating our screens and leaving us swooning over his awkwardness and ability of self-deprecating humor.

It was shown that the sarcasm King often used humor as a defense strategy to negotiate the difficulties of his friendships, sexual relationships, and professional problems. Without a doubt, the charm and sarcasm of Chandler are still etched firmly into our hearts and minds.

Chandler's transformation from a commitment-phobic to a loving spouse and faithful friend is another piece of evidence of the character's development.

Let's dive into our meticulously curated list of the top 10 greatest Chandler Bing episodes. These are must-watches if you want to relive the wit and charm of Chandler.

'Friends' Season 5 Episode 11: When Chandler Bing couldn't remember Joey Tribbiani's sister 

(@nbc)
Matt LeBlanc and Matthew Perry in 'Friends' (@nbc)

In 'Friends' Season 5 Episode 11, Chandler finds himself in an embarrassing predicament while spending Thanksgiving with Joey Tribbiani (Matt LeBlanc), and meeting Mary Angela, one of Joey's several sisters.

But Chandler couldn't recall who his sister Mary Angela was—he'd drunkenly slept with her at Joey's birthday party before.

Chandler's efforts to subtly learn the truth about his affair with Mary Angela lead to a chaotic situation that is both embarrassing and hilarious, displaying the trademark humor and uncomfortable charm that characterized his character throughout the series.

'Friends' Season 5 Episode 14: Chandler Bing and Monica's relationship comes to light 

Matthew Perry's last word on 'Friends' (Netflix/Friends)
A still from 'Friends' (@netflix)

In this episode, Phoebe Buffay (Lisa Kudrow) notices Chandler and, Monica Geller (Courteney Cox), in a precarious scenario. After being astonished for a while, Phoebe decides to mess with the couple and starts flirting with Chandler in an attempt to get them to divulge their secret.

When Monica and Chandler realize Phoebe is after them, Chandler begins to make it seem as if he is really interested in Phoebe by returning her advances. The episode was a laugh riot as Ross returns to Monica's apartment and sees Monica and Chandler presumably making out once again via the peephole.

The episode was a masterwork, as it showed how devoted Chandler was to Monica and how he remained by her even if at first he wanted to flee.

'Friends' Season 7 Episode 5: Chandler Bing's hilarious attempt at taking decent photo 

Chandler Bing tries to smile in front of a camera (Netflix/Friends)
Matthew Perry and Courteney Cox in a still from 'Friends' (@nbc)

Chandler's incapacity to take a decent photo is evident throughout the show, and this episode highlighted that. In 'Friends' Season 7 Episode 5, Chandler and Monica attempt to take engagement photographs, but Chandler's uncomfortable grin spoils the whole shot.

They choose to create fresh engagement photographs with a professional photographer, but Chandler's efforts to be natural in front of the camera are a complete failure. The episode does a great job of highlighting Chandler's foolishness and awkwardness. 

'Friends' Season 10 Episode 15: Chandler Bing's hilarious meeting with his ex Janice 

Matt LeBlanc, Matthew Perry, and David Schwimmer in 'Friends'  (@nbc)
Matt LeBlanc, Matthew Perry, and David Schwimmer in 'Friends' (@nbc)

How can one forget Chandler's ex-girlfriend, Janice Litman-Goralnik (Maggie Wheeler)? Chandler and Monica, who were having trouble leaving their apartment, finally made the decision to settle down in a home they loved, but to their dismay, Janice, who is also interested in the property, shows up.

It was entertaining to see Chandler fight to break free from Janice once again, who still believes that Chandler loves her very much. Janice's crazy and unfiltered laugh from the previous season also brought back memories. 

'Friends' Season 8 Episode 6: Chandler Bing's iconic Halloween Party outfit 

(@nbc)
Matt LeBlanc and Matthew Perry in a still from 'Friends' (@nbc)

Chandler Bing meets some unfortunate situations while dressing up for Monica's Halloween celebration, which brings all of his pals together to celebrate, in this sixth episode of the sitcom's eighth season.

Chandler makes the mistake of dressing up as a pink rabbit when he sees that the other guests are sporting intricate and imaginative costumes.

Chandler and Ross Geller (David Schwimmer) engage in a big arm-wrestling fight in the end, and it's adorable how Chandler keeps winning to Monica to prove himself.

'Friends' Season 4 Episode 12: Chandler Bing's mirthful rivalry with Monica and Rachel 

Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, Matthew Perry, and David Schwimmer in 'Friends'
Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, Matthew Perry, and David Schwimmer in 'Friends'

This episode, where the group competes in a quiz competition, is a prime example of why 'Friends' became a cult favorite. Chandler and Joey find themselves in a hilarious rivalry with Monica and Rachel over who knows whom better—and the stakes are high: the winner gets to keep the loser’s apartment.

Monica and Rachel’s trivia game about each other prompts Joey to boast that he and Chandler know the girls better than they know themselves. Always up for a challenge, Chandler accepts the bet. What ensues is one of the funniest sequences in the series.

The iconic moment when Monica and Rachel are asked about Chandler's job, and in a humorous panic, Rachel blurts out "Transponster," lives in my mind rent-free.

Ultimately, Chandler and Joey emerge victorious and revel in Rachel and Monica's spacious apartment.

'Friends' Season 1 Episode 7: Chandler Bing's hilarious setbacks during city-wide blackout

UNDATED PHOTO:  Actors Courteney Cox Arquette (L), Jennifer Aniston (C) and Matthew Perry are shown
Courteney Cox, Jennifer Aniston and Matthew Perry in a still from 'Friends' (@nbc)

In this episode, Chandler finds himself locked in an ATM vestibule with a stunning woman named Jill Goodacre during a citywide blackout.

You have to see it to fully appreciate Chandler's awkwardness as he tries to strike up a conversation with Jill. His shyness and nervous humor are on full display as he navigates the situation.

Throughout the episode, Chandler battles his claustrophobia and tries to impress Jill with his charm, but his efforts are frequently met with humorous setbacks.

'Friends' Season 4 Episode 8: Chandler Bing's Thanksgiving debacle 

Chandler Bing is comedically humiliated by Julia Roberts' cameo as Susie (Netflix/Warner Bros. Studio)
Matthew Perry and Julia Roberts in 'Freinds' (Netflix/@warnerbrosstudio)

In this episode, Chandler finds himself in an unpleasant circumstance after his kiss with Joey's girlfriend, which completely captures the essence of their relationship.

Chandler chooses to spend Thanksgiving Day inside a big wooden box as a sign of regret and penance as he feels bad about what he did. Chandler stays inside the box for the entire episode while the other friends enjoy Thanksgiving.

At first, Joey won't forgive Chandler, but as the narrative goes on, he comes to regret his rage and misses his buddy. Chandler's sensitivity, devotion to his friends, and readiness to accept responsibility for his errors are the essence of the episode. 

'Friends' Season 6 Episode 13: Chandler Bing's stint with Rachel’s sister

Chandler Bing gets handcuffed in Rachel's boss' office (Netflix/Warner Bros. Studio)
A still from 'Friends' (Netflix/@warnerbrosstudio)

In this comedic gem, Chandler teases Rachel's sister Jill Green (Reese Witherspoon) about her shopping habits when she moves to New York City after her father cuts her off. Chandler's lighthearted teasing is mistaken by Jill for flirtation. Unsettled by her sister's interest in her close friend, Rachel tries to convince Jill not to date Chandler.

Chandler, too, finds himself conflicted. Although he is attracted to Jill, his loyalty to Rachel makes him hesitant to pursue a relationship. Chandler's comedic talents shine in this episode as he navigates the misinterpreted situation.

'Friends' Season 3 Episode 2: Chandler Bing's mishaps during Ross' big event 

Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, and David Schwimmer in a still from 'Friends'  (@nbc)
Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, and David Schwimmer in a still from 'Friends' (@nbc)

As the gang tries to prepare for Ross' big event, Chandler Bing goes through a number of hilarious mishaps.

The episode depicts Chandler's pathetic efforts to take possession of a chair in the flat, but when Joey won't give it up, they engage in a series of comical altercations.

Chandler's sarcasm and irritation provide comic relief throughout the show as he makes his way through the stressful circumstances.

'Friends' is now streaming on Peacock

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