Matthew Perry’s Most Memorable Friends Moments as Chandler Bing

Could he be any more memorable?

As Chandler Bing, Matthew Perry brought the dry humor to Friends, often at his character’s own expense. The beleaguered Bing went through jobs and relationships, though found a happy ending when the series wound down alongside wife Monica Geller (Courteney Cox) and their twin babies.

In his 2022 memoir, “Friends, Lovers, and the Big Terrible Thing,” Perry wrote about how his own unique manner of speech affected his work as Chandler.

The Essence of Chandler

“I read the words in an unexpected fashion, hitting emphases that no one else had hit,” Perry wrote, according to Deadline. “It was as if someone had followed me around for a year, stealing my jokes, copying my mannerisms, photocopying my world-weary yet witty view of life. It wasn’t that I thought I could play ‘Chandler’; I was Chandler.”

Remembering a TV Icon

As fans mourn the loss of Perry, who died on Oct. 28 at 54 years old, it feels appropriate to relive a few of Chandler’s most memorable moments on Friends.

Season 4, Episode 8: “The One with Chandler in a Box”

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In this iconic episode, Chandler voluntarily confines himself to a wooden box as a grand gesture of apology to Joey, who he had wronged by kissing Joey’s girlfriend, Kathy. The box, as Chandler explains, is symbolic of his own self-imposed emotional barriers and serves as a testament to the lengths he will go to mend his friendship with Joey.

Spending Thanksgiving in a box isn’t everyone’s idea of a good time, but Chandler’s stint in his wooden prison brings levity, warmth, and a surprising amount of emotional depth to the episode. Joey eventually forgives him and instructs him to emerge from the box, but not before Chandler gives viewers a lesson in friendship, loyalty, and the capacity for personal growth.

The episode masterfully showcases Chandler’s penchant for using humor as a defense mechanism while also exposing the vulnerable, caring person behind the sarcastic quips. This balance of humor and heart is a hallmark of Chandler Bing, making “The One with Chandler in a Box” a defining moment for the character. Gotcha!

Season 4, Episode 12: “The One with the Embryos”

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Though primarily known for the storyline around Phoebe’s surrogacy, this episode is equally memorable for the high-stakes trivia game that results in Joey and Chandler winning Monica and Rachel’s apartment. Hosted by Ross, the game pits the girls against the guys in a contest of who knows whom better. After several rounds of hilarious yet revealing questions, the game climaxes when Rachel fails to identify Chandler’s job, leading to the guys’ victory and a switch of apartments.

The win is a triumphant moment for Joey and Chandler, characterized by their raucous celebration and gleeful invasion of their new living space. It’s an episode that showcases the dynamics of their friendship and the lengths they’ll go for bragging rights.

This episode encapsulates the essence of Joey and Chandler’s friendship, capturing the camaraderie and playful competition that made their on-screen relationship so relatable and endearing. NICE SHOOTING!

Season 5, Episode 11: “The One with All the Resolutions”

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Chandler takes on the resolution of abstaining from making fun of his friends. However, his struggle against his natural inclination for sarcasm unfolds hilariously as he finds it increasingly difficult to hold back his witty remarks, showcasing the playful and humorous dynamics within the group.

Season 7, Episode 11: “The One with All the Cheesecakes”

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In this episode, Chandler and Rachel find themselves in a comedic dilemma over a mistakenly delivered cheesecake. Unable to resist, they share the cake, only to “borrow” a second one intended for a neighbor. The episode culminates in a hilarious showdown for the last slice, showcasing Chandler’s wit and his knack for finding joy in life’s simple pleasures.

The cheesecake escapade is a standout moment, embodying Chandler Bing’s irreverent charm and making it a timeless favorite among fans.

Season 7, Episode 5: “The One With The Engagement Picture”

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Chandler struggles to put on a genuine smile for an engagement picture with Monica, leading to a series of humorous attempts. His awkward smiles reflect his quirky and endearing personality, while also portraying the genuine effort he puts into making significant moments special for Monica.

Season 4, Episode 18: “The One with Rachel’s New Dress”

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Phoebe offers to name one of her babies after one of the guys, but Joey’s disapproval of his name as “stupid” leaves Chandler on a quest for a new name. He settles on Clint, but is playfully mocked by Joey and Phoebe who claim he lacks the coolness to pull it off. They teasingly refer to him as Gene, amusing themselves at Chandler’s expense, showcasing the friendly banter and camaraderie that often colors their interactions.

Season 2, Episode 13: “The One After the Superbowl: Part 2”

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Any post-Super Bowl episode usually guarantees a winner, and this one didn’t disappoint. It brought in guest star Julia Roberts — who was actually Perry’s off-screen girlfriend at the time, as he revealed in 2022. In the episode, she played Susie Moss, an old classmate who left Chandler basically naked in a bathroom as revenge for an embarrassing moment he caused her in elementary school.

Season 6, Episode 24: “The One with the Proposal”

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In a two-part season finale, Chandler’s heartfelt proposal to Monica stands as one of the series’ most emotional peaks. Initially attempting a casual approach to throw Monica off the scent of his intentions, Chandler soon finds himself overwhelmed by the gravity of the moment. Ultimately, it’s Monica who starts the proposal, and Chandler who tearfully finishes it, resulting in a deeply moving scene that brings them, and viewers, to tears.

The proposal is a pivotal event not just for Chandler and Monica, but for the series as a whole. It marks a significant turning point in their relationship and sets the stage for their life together as a married couple.

Chandler’s vulnerability during the proposal is a departure from his usual sarcasm and wit, revealing a depth of emotion that adds layers to his character. The moment is a powerful testament to the series’ ability to balance humor with heartfelt sincerity.

Season 5, Episode 14: “The One Where Everybody Finds Out”

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As the friends discovered one by one that Monica and Chandler were an item, each episode became a treasure chest of hilarity and touching moments. The characters each had their fun reactions, leading to some of the best laughs of the series.

Season 4, Episode 15: “The One with All the Rugby”

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Who can forget the time Chandler tried to dodge his annoying ex Janice by saying he was moving to Yemen? He went as far as to drop more than $2,000 on a plane ticket just to avoid an uncomfortable confrontation at the airport. Well then I guess I’m going to Yemen!

Season 4, Episode 11: “The One With Phoebe’s Uterus”

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In a humorous moment, Chandler, played by Matthew Perry, flubs his line, leading to an improvised exchange among the cast. Ross, Rachel, and Monica react to the line mishap in character, making light of Chandler’s misstatement about a blue blazer, while the scene also introduces Joey’s new job at the American Museum of Natural History, bringing comedic elements to the episode’s narrative. You messed it up.. You’re stupid.

Season 4, Episode 3: “The One with All The Cuffs”

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In this memorable episode, Chandler finds himself handcuffed in Rachel’s boss Joanna’s office. He spends hours alone, contemplating his life choices and begging for freedom when Rachel and Sophie, Joanna’s assistant, find him. The awkwardness hits a peak when Rachel has to decide whether or not to free him before Joanna returns. This situation, like so many of Chandler’s experiences, combines embarrassment with a dose of laugh-out-loud humor, cementing its place as one of the character’s unforgettable moments.

The predicament Chandler faces—being physically restrained while emotionally trapped—serves as a hilarious but poignant metaphor for many of the character’s own personal struggles throughout the series. Fun fact: Perry gets hit in the head with the filing cabinet by accident and they kept it in the final cut. FREEDOM! I WANT MY FREEDOM! WHY WON’T YOU HEAR ME! SOPHIE! HELP ME!

Season 5, Episode 14: “The One Where Everybody Finds Out”

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Phoebe discovers Chandler and Monica’s relationship and decides to test its seriousness by attempting to seduce Chandler. Unbeknownst to her, Chandler and Monica are indeed seriously involved. This leads to an amusing cat-and-mouse game where Phoebe and Chandler exaggerate their interests in each other to see who cracks first, providing a comedic yet tender exploration of the lengths the couple will go to protect their relationship, while also showcasing the close-knit, playful dynamic among the group. She knows!

Season 3, Episode 11: “The One Where Chandler Can’t Remember Which Sister”

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Chandler finds himself in hot water after a New Year’s Eve party where he kisses one of Joey’s many sisters but can’t remember which one. The next day, Joey demands that Chandler make it right, but Chandler’s inability to identify the sister leads to a hilarious and awkward confrontation with all seven Tribbiani sisters in Joey’s family home.

This episode highlights Chandler’s characteristic mix of good intentions and hapless execution. His efforts to smooth over the situation only dig him deeper into trouble, culminating in a comedic moment that fans love for its awkward hilarity. This is so bad!

Season 3, Episode 8: “The One with the Giant Poking Device”

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In a classic episode that primarily centers around the group’s concern for Ugly Naked Guy’s well-being, a lighter subplot emerges featuring Chandler and Phoebe. They share a spontaneous duet of “My Endless Love,” originally by Lionel Richie and Diana Ross, as they sit in the coffeehouse Central Perk. The unexpected duet serves as a comical detour from the episode’s primary storyline, adding a touch of levity and showcasing the unique chemistry between these two characters.

The moment is brief but iconic, perfectly encapsulating the show’s blend of humor and heart while emphasizing Chandler’s ability to find comedy even in the most mundane situations. My Endless Love

Final Thoughts

Matthew Perry’s portrayal of Chandler Bing will always remain etched in our memories and hearts. His dry wit, idiosyncratic mannerisms, and deep emotional moments made the character so relatable. We’ll always be thankful for the laughs and lessons that Perry, through Chandler, gave us.

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