The Late Mathew Perry’s Greatest Chandler Bing Moments

By: Ronnie Tal | Published: Nov 21, 2023

Matthew Perry has been cemented into the Pop Culture Hall of Fame if there ever was one. His iconic character, Chandler Bing, in the cult classic show, “Friends” is what will undoubtedly be remembered for generations to come.

But before you hop on the couch and watch “Friends” reruns let’s take a moment to honor the late Matthew Perry by giving his impeccable comedic timing and showman brilliance the recognition it deserves. You’ll be laughing and crying like you have never before by the time you’re done with this countdown.

Living in a Box

After Chandler’s smooch with Joey’s girlfriend, he’s on a mission to mend fences. Considering Joey’s recent cabinet caper during a robbery, Chandler faces an unusual penance: spending Thanksgiving in a box. It’s a quirky idea that somehow fits the show’s humor perfectly. Joey’s suggestion sparks a comical escapade, highlighting


Source: NBC / Friends

Matthew Perry’s knack for delivering laughs with just his voice. The Thanksgiving-in-a-box escapade turns into a sidesplitting example of the show’s ability to turn wacky situations into pure, lighthearted hilarity, showcasing the cast’s comedic chemistry and making for a memorable holiday misadventure.

(Season 4, Episode 8, “The One With Chandler In A Box”)

The Heroic Journey to Yemen

The ridiculous pair of Janis and Chandler delivered countless memorable moments, but their pinnacle interaction occurs when Chandler, desperate to get rid of her, fabricates a relocation tale – claiming that he’s bound for Yemen. The comedy unfolds when Janis, unsuspecting, accompanies him to the airport, with unlucky Chandler realizing that his journey might just turn out to be real.


Source: NBC / Via Netflix / Friends

In a classic Chandler fashion, he turns to an elderly lady, deadpanning, “When we get to Yemen, can I live with you?” This comedic twist is the pinnacle of Chandler’s quick wit and the absurd humor that made their exchanges a highlight in the Friends series.

(Season 4, Episode 15, “The One With All the Rugby” )

Chandler and Phoebe’s Fake Date

This Friends classic gives us the iconic line, “They don’t know that we know that they know we know.” The chaos kicks off when Phoebe catches Monica and Chandler in the act, setting the stage for a hilarious game of cat and mouse. Lisa Kudrow shines as Phoebe, but Matthew Perry steals the scene, especially when he playfully invites Phoebe to “feel his bicep… and maybe more.”


Source: NBC / Friends

His impeccable delivery, praising Phoebe’s bra with a casual “It’s very nice” and expressing excitement about “having all the sex,” makes this one of Chandler’s comedic peaks. As a delightful bonus, the episode features Chandler’s sweet declaration of love to Monica.

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

A Smoking Battle Worse Than the Gun

In the epic battle against nicotine, Chandler gets a hypnosis tape from Rachel to quit smoking. But wait, plot twist—it’s a gender-specific tape, made for women. Now, Chandler, armed with his unintentional crash course in femininity, starts exhibiting what society considers “girly” traits.


Source: NBC / Friends

It’s a laugh riot as he unintentionally embraces his newfound womanly wisdom. The episode becomes a hilarious rollercoaster of Chandler trying to kick the smoking habit while accidentally dabbling in gender stereotypes. 

(Season 3, Episode 18, “The One with the Hypnosis Tape”)

His Halloween Humiliation

Monica takes charge of Halloween, unleashing Chandler’s inner pink bunny in a costume that screams, “I’m confident in my masculinity, but also, I look ridiculous.” Monica, perpetually stunning, struts as Catwoman, making us wonder if there’s any costume that could make her look less than fabulous.

Source: NBC / Friends

Chandler, faced with the pink bunny debacle, deadpans, “It was the pink bunny or no bunny at all.” Classic Chandler.  Amidst the hilarity, Chandler’s persistent attempts to impress Monica add a dash of sweet absurdity to the Halloween shenanigans.

(Season 8, Episode 6, “The One With the Halloween Party”)


Making His Case For Monica

In one of his most heartfelt moments, Chandler opens up about his and Monica’s desire to adopt, delivering an emotional monologue that tugs at the heartstrings. Acknowledging Monica’s incredible qualities, he confesses, “She’s loving and devoted, and the woman’s always right.” Chandler reveals the painful reality that they can’t conceive, expressing his deep longing for fatherhood.

Source: NBC / Friends

He paints a poignant picture of Monica as a mother without a baby, declaring, “She’s already there.” Chandler’s plea is both touching and sincere as he implores Erica to consider them. The emotional weight of his words captures the essence of the couple’s journey towards parenthood.

(Season 10, Episode 9, “The One With The Birth Mother”)


The Not-So-Close Closure With Janice

In the grand finale, Monica and Chandler make the leap to suburbia, turning their house-hunting adventure into a sitcom rollercoaster. Picture this: their dream home is on the line, and who swoops in at the last minute to spice things up? None other than the vivacious Janice.

Source: NBC / Friends

Chandler, aiming for closure with his lovably persistent ex, faces comedic twists. The chuckles escalate as Janice, in classic fashion, remains convinced of Chandler’s lingering affection, despite all signs pointing otherwise. Amid suburban dreams, their quirky farewell becomes a light-hearted dance of mistaken affections, leaving us with laughs and a suburban welcome mat.

(Season 10, Episode 15, “The One Where Estelle Dies”)


When the Camera Didn’t Like Him

Monica’s mission for the ideal engagement photo turns into a sidesplitting comedy when she discovers Chandler’s “unique” approach to posing. Chandler, despite his best efforts, seems to have a talent for transforming his genuine smiles into delightful, albeit unintentional, grimaces as soon as the camera clicks.

Source: Friends Wiki Fandom / NBC / Friends

Matthew Perry’s comedic genius shines through in this episode, making it a delightful highlight of Friends’ 10-year journey. Chandler’s consistent photogenic mishaps become a whimsical spectacle. 

(Season 7, Episode 5, “The One With the Engagement Picture”)


Getting Down on One Knee

Buckle up for a feel-good ride! In a heartwarming Friends moment, Chandler, in his signature overthinking style, grapples with the big question: Is he ready to marry Monica? But surprise! He returns home to find Monica on one knee, proposing. Plot twist, right? In a twist of fate, Chandler ends up flipping the script, popping the question, and sliding a ring on Monica’s finger.

Source: goodinfo / NBC / Friends

Cue the waterworks from Mon and the entire studio audience. Matthew Perry, known for his comedic chops, delivers a touching performance, reminding us that, yes, even in the sitcom world, love conquers all, and proposals can be hilariously heartwarming.

(Season 6, Episode 25, “The One With The Proposal”)


Chandler’s Adventures During the Blackout

Imagine Chandler, the awkward maestro, caught in an ATM vestibule during a city blackout. Plot twist: Victoria’s Secret model Jill Goodacre is his unexpected co-star. In a comedic ballet, early scenes see Matthew Perry orchestrating Chandler’s discomfort with minimal words.

Source: Chandler Bing Humor / Facebook / NBC / Friends

He relies on expressive body language while his inner thoughts play in voiceover. It’s a comedic highwire act Perry pulls off flawlessly. Let’s call it Chandler’s ballet of awkwardness. Perfection? Oh, absolutely.

(Season 1, Episode 7, “The One With the Blackout”)


Mondler’s First Time

Delving into Season 4’s escapade, that time when Monica and Chandler end up sharing a bed in London. The pairing of Monica’s sweet Type A personality with Chandler’s endearing neuroticism is pure comedic magic. Picture it as a whimsical dance, each neurotic quirk and sweet gesture contributing to the symphony of laughter in their relationship.

Source: Alexis Prestwich / Pinterest / NBC / Friends

From across the pond to the heart of Friends’ humor, Chandler and Monica whip up a charming blend of love and hilarity that leaves us spoiled for choice in the buffet of their delightful moments.

(Season 4, Final Episode, “The One With Ross’ Wedding Part 2”)


Kathy, "The Girl of My Dreams"

The rare glimpses of NYC’s main streets in Friends always deliver a punch of fun, and this scene is no different. Picture Chandler’s comedic marathon as he ‘casually’ tries to run into Kathy, weaving through traffic with wild determination. It’s a hilarious spectacle of frenetic energy, proving that Chandler’s attempts at nonchalant encounters are the epitome of slapstick gold.

Source: Warner Brothers / Buzzfeed / Friends - NBC

As he dashes through the bustling city, dodging pedestrians and narrowly escaping traffic chaos, it’s a whimsical reminder that even in the chaotic dance of New York, Chandler’s pursuit of comedic moments stands out.

(Season 4, Episode 7, “The One Where Chandler Crosses a Line”)


Fighting the Feels

Beyond the classic season-ending engagement to Monica, there’s another comedic gem showcasing Perry’s wit and impeccable timing. Monica’s discovery that Chandler hasn’t shed a tear since childhood triggers a quest to crack the emotional vault. Perry’s brilliance shines with a memorable line: “Well, that makes me feel all warm inside my cold tin chest.”

Source: Twitter ( X ) / Friends / NBC

The tear floodgates finally open when Chandler, moved by Ross and Rachel’s tumultuous relationship, breaks down. Perry’s comedic finesse elevates the laughter and proves that even Chandler’s emotional side is a spectacle.

(Season 6, Episode 14, “The One Where Chandler Can’t Cry”)


When He Was Pranked by Julia Roberts

Behold the iconic snapshot of hilarity! Picture this: Julia Robet’s Susie asks Chandler to don her panties for dinner, only to leave him stranded, stark naked, in the bathroom. The seamless integration with Joey and Ross adds a perfect punch to the scene.

Source: Twitter (X) / NBC / Friends

Chandler, caught in an absurd fashion fiasco, becomes the unwitting star of a sitcom symphony. It’s a laugh-inducing tableau of wardrobe mishaps and comedic camaraderie, reminding us that even in the wacky world of Friends, the unexpected and the uproarious converge to create timeless moments of lighthearted hilarity. 

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


The Sister Switch

In the aftermath of discovering that his ex, the unforgettable Janice, is now happily married with a baby on the way, Chandler seeks solace in Jell-o shots at Joey’s birthday bash. However, he ends up entangled with one of Joey’s sisters, but there’s a hiccup—he can’t recall which one.

Source: Yarn / NBC / Friends

With Ross as his bumbling wingman, Chandler embarks on a quest to identify the mystery sister, aiming to visit the Tribbiani home and ask for Mary Angela, the accidental smooching partner. Naturally, chaos ensues during a family dinner with all the sisters present, culminating in a well-deserved punch.

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


Gaslighting the Gaslighter

Enter Eddie, whose quirky antics become the playground for Chandler’s classic reactions, delivering prime comedy moments. While the dynamic might carry a hint of yesteryear sitcom tropes, particularly with Chandler’s amusingly over-the-top responses, it’s all in good fun.

Source: NBC / Friends

Picture Perry navigating the eccentricities of his offbeat roommate with a mix of puzzled expressions and good-natured eye rolls, culminating in him totally and completely banding Eddie’s concept of reality in response to his constant gaslighting. Between the dried-up fruit, the so-called goldfish, and Chandler’s loose nerves, this was one of Perry’s best acting displays.

(Season 2, episode 19, “The One Where Eddie Won’t Go”)


Chandler’s Quarter-Life Crisis

In a touching Season 2 episode, Chandler bares his softer side amid the clutter of cleaning Heckles’ place. There he uncovers an unexpected connection—they both earned the title of high school Class Clown and shared a penchant for overlooking potential partners’ minor flaws.

Source: Reddit / NBC / Friends

Initially fearing a solitary fate, Chandler undergoes a heartening transformation. Realizing he doesn’t have to mimic Heckles, he takes a bold step in his romantic life, finally asking out a colleague he’d been avoiding due to her “large head.” 

(Season 2, Episode 3, “The One Where Heckles Dies”)


Body Shaming Monica, and Paying the Price

In this timeless flashback gem, after unknowingly fat-shamed Monica right in front of her, Chandlers comes back the following year only for Monica’s newfound confidence to take center stage, and poor Chandler to bear the brunt of her exuberance.

Source: NBC / Friends

Picture Monica’s over-the-top antics and Chandler trying to keep up with her whirlwind of enthusiasm. It’s a classic case of comedic misadventure that showcases the duo’s dynamic and adds a generous dose of hilarity to the Friends tapestry. The cherry on top would be their heart-to-heart at the end of the episode, always an amazing testimony to Perry’s range.

(Season 5, Episode 8, “The One with All the Thanksgivings”)


Perry’s Incredible Physical Comedy

One of the qualities that made Chandler such a beloved character is undoubtedly Matthew Perry’s true gift of expressing himself physically in his acting. In this small but very telling scene from season 4, Chandler expresses just how uncoordinated he is, and why it jeopardizes every chance he may have of picking up women at a wedding- where the dance party is part of the main event.

Source: NBC / Friends

In the few seconds long part where Chandlers demonstrates his dancing ability (or inability, in that case) he steals the entire show, and our hearts with it.

(Season 4, Episode 20, “The One With All the Wedding Dresses”)


What’s In a Name

Step into one of Chandler’s most relatable moments: a colleague accidentally labels him Toby, and instead of setting the record straight, he opts to let the misnomer slide. The reason? A delectable donut is hanging in the balance! Who hasn’t chosen the sweet allure of a donut over the mild inconvenience of a name correction?

Source: YARN / NBC / Friends

Sure, not all of us have gone so far as trashing our own offices in pursuit of pastry perfection, but Chandler’s dilemma is a delightful reminder that life’s quirks often lead us down unexpectedly funny paths. 

(Season 8, Episode 5, “The One with Rachel’s Date”)


He’s Only Human

“Friends” was revolutionary in many ways, one of which was their portrayal of Ross’ ex-wife Carol and her partner Suzan’s wedding. But like all commitment-related events, it brought up some of Chandler’s worst and most hilarious impulses. Walking around the wedding venue, he felt more inept than ever, even walking up to one of the lady guests, making eye contact, and realizing- out loud- that there was not even a point in him coming up with a pickup line!

Source: YARN / NBC / Friends

The cringe-inducing scene doesn’t end there, but the result stays all the same. We are all people, but some of us just don’t match up!

(Season 2, Episode 11, “The One With the Lesbain Wedding)


His Naughty Little Treat

In a delightful rarity, Chandler and Rachel team up for a comedic gem that hits all the right notes. The stolen cheesecake from Mama’s Little Bakery in Chicago, Illinois becomes an obsession, leading to a cute and hilarious resolution: indulging in the forbidden treat off the floor.

Source: NBC / Friends

The duo’s playful banter and shared cheesecake caper create a scene that’s both endearing and uproarious. It’s a lighthearted escapade that showcases Friends’ knack for turning stolen sweets into sweet comedic moments.

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


Bath Time!

This gem from Season 8 aged up pretty well—especially in the current era of wellness and self-care. Monica introduces him to the world of baths, and behold Chandler, sinking into relaxation with Enya’s “Who Can Say” while cradling his manly toy boat. Addiction sets in, and he boldly swipes Monica’s bath, turning the bathroom into a bustling hangout.

Source: NBC / Friends

Amidst the later-season awkwardness of Joey’s crush on Rachel, this episode emerges as a lighthearted highlight, blending humor, self-discovery, and the whimsical camaraderie of the Friends gang.

(Season 8, Episode 13, “The One Where Chandler Takes a Bath”)


The Accidental Lapdance

When Chandler attempts a bonding session with Ross and Monica’s dad through a spirited game of racquetball, you already know that it’s bound to be hysterical. Post-match, the trio ventures into a steam room, where Chandler’s glasses fog up, rendering him temporarily blind. In an accidental, and quite naked, comedy of errors, Chandler finds himself sharing an unexpected lap session with his future father-in-law, who’s equally in the buff.

Source: NBC / Friends

It’s a hilariously steamy mishap that unfolds in classic Friends fashion, proving once again that even the best-laid plans for male bonding can take unexpected, and uproarious, turns.

(Season 7, Episode 3,  “The One With Phoebe’s Cookies”)


Chandler the Mastermind

Chandler’s ingenious scheme to support Joey’s finances through the fictional card game “Cups” became a comical escapade in the Friends’ apartment. With each hand played, Chandler spun elaborate excuses to hand over money, successfully losing a whopping $1,500.

Source: Reddit / NBC / Friends

However, hilarity ensued when the well-intentioned Joey decided to teach the non-existent game to Ross, unwittingly causing the entire windfall to vanish in a cascade of fictional cups and imaginary cards. 

(Season 6, Episode 6, “The One on the Last Night”)


The Kissing Fiasco

In the wild kickoff of Season Five, Chandler turns goodbye kisses into a sitcom spectacle. After he and Monica casually exchange a kiss goodbye, forgetting that they’re not alone, they leave Phoebe and Rachel stunned. Panic mode: activated. To diffuse the awkwardness, Chandler goes full-on “culture ambassador,” planting kisses on everyone. Picture the chaos: lips meet in a comedic dance of confusion.

Source: silvia musciaglia / Pinterest / NBC / Friends

Chandler’s attempt at smooth damage control turns into a laugh-out-loud disaster, proving that in the Friends universe, even the simplest goodbyes are packed with unexpected hilarity. Because when Chandler tries to bring “culture” to the gang, you can bet it’ll be a sidesplitting show.

(Season 5, Episode 2, “The One With All the Kissing”)


A Nap and Its Price

Perry starts off with an absolutely amazing tired-out-of-his-mind performance which culminates in one of the best shocked expressions in TV history. His later attempt to break the news to Monica about their sudden move to Oklahoma. Picture him stumbling over words, desperately trying to explain that a nap in a work meeting led to this wild decision.

Source: Twitter (X) / NBC / Friends

Monica’s disbelief and Chandler’s comedic excuses collide, creating a laugh-out-loud symphony. It’s everything we could’ve wished for and more in the Friends universe.

(Season 9, Episode 2, “The One Where Emma Cries”)


Living His Dreams

Season 9 sees Chandler on a quest for a career facelift (because, let’s face it, no one really knew what he did before). Landing an internship at an advertising agency, he’s suddenly the old-timer among sprightly colleagues. Yet, in this generational tug-of-war, Chandler’s genius emerges.

Source: Quora / NBC / Friends

Faced with a pair of horrendous sneakers, he conjures up a slogan so witty it almost distracts from the shoe atrocity. It’s a comic crescendo in Chandler’s career saga, proving that even in the perplexing world of advertising, where bad sneakers roam, Chandler’s quick wit prevails as the unsung hero of hilarity.

(Season 9, Episode 15, “The One With the Mugging”)


Unscripted Magic

Behold Chandler’s accidental triumph, arguably his most iconic moment. A set mishap turned comedic gold, Matthew Perry flawlessly rolls with the punches. The scene with Rachel is a riot, but the pièce de résistance? A fist pump turned forehead collision with a drawer.

Source: Pinterest / NBC / Friends

Chandler’s inadvertent rendezvous with furniture becomes a classic, reminding us that sometimes the best laughs are the unplanned ones—especially when delivered with Perry’s unparalleled comedic finesse. In the annals of Friends, this moment stands as a testament to Chandler’s enduring charm and comedic legacy.

(Season 4, Episode 6, “The One With the Cuffs”)


Perry’s Closing Line

In the poignant farewell to their iconic apartment, Monica and Chandler, with twin babies in tow, trigger a cascade of teary-eyed goodbyes. The emotional climax takes a comedic twist as Rachel proposes one last coffee meet-up. Exiting the door, Chandler, master of the punchline, drops the curtain on the series with his classic wit: “Where?” It’s the perfect parting quip, a nod to the gang’s perpetual coffee shop gatherings, and a final laugh that echoes in the hearts of fans. Chandler, forever the maestro of humor, leaves the series on a high note, ensuring Friends concludes with a comedic flourish.

(Final Episode, “The Last One”)

Source: NBC / Friends

Matthew Perry’s portrayal of Chandler Bing in Friends remains a comedic masterclass, etching an indelible mark on television history. As the witty, sarcastic, yet endearing character, Perry delivered Chandler’s punchlines with impeccable timing, making him a fan-favorite. Beyond the laughs, Perry’s influence extended behind the scenes. In his memoir, Friends, Lovers, and the Big Terrible Thing, he reveals a pivotal moment before the final episode. Taking Marta Kauffman aside, Perry argued for Chandler’s final quip, understanding its resonance. “None of his co-stars will care about this except me,” he asserted, securing the iconic curtain-closing line. Perry’s imprint on Friends reaches beyond the screen, a testament to his comedic brilliance and dedication to the character that forever solidified his place in sitcom history.