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12 Funniest Chandler Bing Moments In Friends

Fans have been reacting to the passing of Matthew Perry with grief and disbelief. But mostly, there has been an outpouring of gratitude to the actor for bringing so much joy to audiences, even though he sometimes struggled to find his own. From 1994 to 2004 — and beyond thanks to streaming services — Perry made millions of people laugh playing the sarcastic but loveable Chandler Muriel Bing in "Friends."

Even as he was in the throes of addiction while filming the wildly popular TV show — something he spoke candidly about in his 2022 memoir, "Friends, Lovers, and the Big Terrible Thing" — he never allowed it to affect his ability to keep his stellar comedic timing and deliver a sardonic (and often touching) performance alongside his five co-stars.

Chandler himself said: "I'm not great at the advice. Can I interest you in a sarcastic comment?" Few quotes sum up Chandler as well as this one, and the character's well-intentioned sarcasm and quips were something that came naturally to the actor who played him. Per his memoir, Perry believed he was Chandler, and so did we. At least one hilarious Chandler moment can be found in every one of the 236 episodes of "Friends," so there are plenty to choose from. Here are 12 of the funniest Chandler Bing moments.

Chandler's parachute is a knapsack

One of the main plot threads in Season 1 of "Friends" is Ross' (David Schwimmer) divorce from his pregnant wife, who has recently come out as a lesbian. In Season 1, Episode 23 ("The One with the Birth"), Carol (Jane Sibbett) gives birth to their son, Ben. 

When Carol goes into labor, the entire group of friends go to the hospital to wait for the arrival of Ross' first child. While waiting, Monica (Courteney Cox) envies the new mothers as they pass through the maternity ward with their new bundles of joy.

Currently single, Monica worries that she may never get the chance to be married and pregnant. Chandler tries to offer a deal that if they are both single when they turn 40, they can have a baby together. Monica, slightly insulted by the suggestion that she won't be married by 40, demands that Chandler explain himself. Realizing he has put his foot in his mouth, Chandler quips, "Dear God! This parachute is a knapsack!" as he feigns a dramatic escape, rolling over the back of the chair. It is one of Chandler's more surreal comebacks, but it doesn't make it any less amusing.

Joey's tailor is a bad man

Joey (Matt LeBlanc) is known for his popularity with the ladies, but not being the sharpest knife in the drawer shall we say, and it's common for the group of friends to explain some of life's most simple occurrences to him. In Season 2, Episode 1 ("The One with Ross' New Girlfriend"), Chandler is looking to get some pants altered. Conveniently, Joey happens to have a tailor, Frankie (Buck Kartalian), whom he recommends to help Chandler.

When Chandler returns from his alteration session, he is visibly upset and traumatized as he beckons for Joey's attention, exclaiming that his tailor is "a very bad man." He explains that the tailor's method of measuring his inseam must be revised to industry standard. The tailor took some liberties with inappropriate "cupping" as he took Chandler's measurements, making him feel taken advantage of. Joey defends his tailor, insisting that is how "they do pants." After Ross confirms that Frankie has been measuring Joey and his father inappropriately all of these years, the sometimes dim friend spends the rest of the episode trying to process the information. Chandler's ever-changing facial expressions throughout this exchange are not only incredibly funny but really sell his frustration.

Is Chandler Mr. Heckles?

Rachel (Jennifer Aniston) and Monica's downstairs neighbor, Mr. Heckles (Larry Hanklin), has a habit of randomly coming up to complain about the excessive noise. Oftentimes, the complaints were without merit. In Season 2, Episode 3 ("The One Where Heckles Dies," Mr. Heckles, well ... dies. In a surprise turn of events, he leaves all his possessions to the "noisy girls in the apartment above mine."

Upon entering Heckles' apartment, it's clear that he has never thrown anything away. Among the piles of papers and books, they find an old high school yearbook and see that he was once a very likable person. Chandler finds that he and their eccentric neighbor share quite a few similarities, like being voted class clown and playing the clarinet in band. The most troubling similarity Chandler finds is that Heckles was also highly picky about the women he dated.

Chandler finds a box full of photos of Heckles' old girlfriends he once rejected, and is worried that he is on the path to becoming Heckles and dying alone. He works himself into a frenzy and decides if he's going to become a lonely old man, he needs a hook and settles on becoming the Crazy Snake Man. It's always fun to see Chandler this unhinged, yet the episode closes with a surprisingly touching moment when Chandler switches the lights off in Heckles' apartment — saying farewell to the old man and hopefully, his chances of turning into him. 

Chandler overshares

Chandler's relationship with his parents is complicated, and he shares many childhood stories that leave his friends puzzled and concerned. In Season 3, Episode 1 ("The One with the Princess Leia Fantasy"), Rachel gets Ross to admit that his secret fantasy is of Princess Leia in the gold bikini from "Star Wars: Episode VI – Return of the Jedi." Of course, Rachel immediately tells the girls, and they tease Ross about it. 

Thinking Rachel would keep his secret, Ross is slightly embarrassed when word gets out, and he complains to Chandler that women tell each other everything. Hesitantly, Ross tells Chandler about his fantasy, and Chandler — familiar with Princess Leia and her gold bikini — agrees that it's a good one. They both get a chuckle, and Chandler takes a turn at this sharing thing.

Chandler says that sometimes, during sex, he will get random images in his head, like Elle Macpherson and the girl from the copy place. But occasionally, through no fault of his own, an image of his mom will pop up. But he won't stop doing what he's doing, and that makes him ... uncomfortable, to say the least. However, no one is more uncomfortable than Ross in this situation, and Chandler panics when he realizes Ross can not relate to this horror. Ross tells him he "said, 'share,' not 'scare,'" and puts Chandler on a time-out, hoping they never speak of this again. This moment is a great example of Chandler's endearing — and hilarious — awkwardness.

Chandler in cuffs

One of the many running gags in "Friends" is that Chandler isn't always successful with the ladies. In Season 3, Chandler goes on a couple of dates with Rachel's extremely demanding boss, Joanna (Alison La Placa). Chandler, who thinks she's a "big dull dud," breaks it off before anything can begin. Moving on to Season 4, Episode 3 ("The One with the 'Cuffs"), Chandler runs into Joanna again and they start a sexual relationship — much to Rachel's dismay. Rachel begs him to end things with Joanna, but Chandler is unable to do so.

One afternoon, after a romp in her office, Joanna gets a call that her boss needs to see her now. She handcuffs a pantless Chandler to her chair and locks him in the room. Rachel, who secretly has a key to Joanna's office, goes in to snoop but finds an embarrassed Chandler instead. Ready to leave, Chandler asks Rachel to unlock him. She does so but quickly regrets it, realizing how angry Joanna will be when she discovers Rachel has a key.

Rachel pleads with Chandler to get back in the chair but, in a desperate act, handcuffs him to the filing cabinet. This act doesn't help to keep her secret, and Chandler really wants out. Frustrated — and in an unscripted move – Chandler sighs, "Will you please just ..." while gesturing for emphasis and the cuffed arm pulls the drawer into the back of his head. This unplanned moment is made even funnier by the fact he always keeps eye contact with Rachel.

Chandler moves to Yemen

Chandler's on-again-off-again relationship with Janice (Maggie Wheeler) is the stuff of legend, and his feelings for her are super complicated. One minute, he is deeply in love with her, and the next, he can't stand the woman. During a lull in his dating life, in Season 4, Episode 15 ("The One with All the Rugby"), Chandler runs into Janice, who is ready to start their romance again. In a cowardly move, and instead of just breaking up with her, Chandler tells Janice he is moving to Yemen.

Because Janice insists on soaking up as much time with him as possible, Chandler doubles down and takes this terrible plan all the way to the airport. He desperately tries to get the ticket agent in on his scheme, hoping she will give him a fake ticket to Yemen, but it's a no-go and Chandler reluctantly purchases a $2,100 ticket and goes to board the plane.

Thinking it's safe, he doubles back and tries to breeze past Janice as she calls after him. Janice has beaten him at his own game and is determined to watch his plane take off. Defeated and close to tears, Chandler boards the plane, asking an older woman, "When we get to Yemen, can I stay with you?" It's hard to condone Chandler lying to Janice, but it is undeniably hilarious to see the limits he is willing to go to in order to avoid confessing.

Chandler can't be funny

New Year's resolutions are all fun and games until you have to stick to them. In Season 5, Episode 11 ("The One with All the Resolutions"), the gang rings in 1999 with plans to better themselves. Ross commits to trying something new every day, Rachel pledges not to gossip, Joey says he will learn to play guitar, and Chandler resolves to stop making fun of his friends. No one in the group believes he is capable of this and Ross bets him $50 that he won't last a week. 

Chandler's friends don't exactly go easy on him, with Ross uncharacteristically wearing leather pants and dating a girl with the last name "Hornswaggle," and Phoebe (Lisa Kudrow) sharing her very literal names for guitar chords including the "Turkey Claw." 

Keeping all of the jokes to himself seems to be causing him physical pain, and he finally breaks. During the end credits, Chandler storms into Central Perk and hands Ross the $50, before spitting out all the one-liners he's been holding in and collapsing onto the couch with a sigh of relief. Ironically, Chandler not being allowed to be funny is just as funny — if not more so — for the audience.  

Chandler tries to seduce Phoebe

When Chandler and Monica started dating, they were determined to keep it a secret. Eventually, Joey and Rachel found out and were forced to keep the secret. While taking a tour around Ugly Naked Guy's (Jon Haugen) apartment with Ross – who is looking to rent it — Phoebe accidentally witnesses Chandler and Monica having sex from across the way.

In Season 5, Episode 14 ("The One Where Everybody Finds Out"), Joey wants to come clean, but Phoebe sees this as an opportunity for a bit of fun. She starts flirting with Chandler, pretending to want to take things to the next level. Monica and Chandler figure out what she's up to and play the long game to call her bluff.

The final showdown involves Phoebe and Chandler going toe to toe, trying to win at the art of seduction. Both are nervously waiting for the other to break as they awkwardly make advances towards one another. He goes to grab her breast but can't go through with it and hilariously moves his hand to her shoulder instead. From their open-eyed kiss to Chandler tensely proclaiming that he's "very happy we're gonna have all the sex," this scene is one of the cringiest and funniest Chandler Bing moments in the best possible way.

Chandler pivots a couch

Possibly one of the most quoted episodes of "Friends," Season 5, Episode 16 ("The One with the Cop") sees Ross move into Ugly Naked Guy's old apartment and treat himself to a brand new couch. He's pretty pleased with the purchase but refuses to pay for delivery. Rachel has come shopping with him, and he is convinced they can get it to his apartment, three blocks away. They manage to get it to the elevator-less building, however, they run into problems when getting it up the stairs.

Being the only friend available, Rachel grabs Chandler for assistance. Agreeing that he is last on the list of good choices to move a couch, Chandler reluctantly follows Ross' orders, complete with a sketch.

The awkward stairwell does not lend itself well to moving a couch, but Ross has a solution: To continuously yell "Pivot!" as they attempt to maneuver the couch around the tight corners. Pressed between the couch and wall, an exasperated Chandler screams for Ross to "Shut up! Shut UP! SHUT UP!!" A defeated Ross admits they might have a problem, and Chandler calmly offers one last sarcastic suggestion when he asks, "What did you mean when you said pivot?" While Ross' line may be the one that "Friends" fans still quote now, Chandler's brilliant response is underrated and perfectly delivered. 

Chandler and Monica find a date for Rachel

In Season 6, Episode 19 ("The One with Joey's Fridge"), Rachel needs a date for her charity ball that her boss, Ralph Lauren, is hosting. She asks her friends to set her up with a guy for the night who either "has his own tux, or the ability to rent a tux." Phoebe finds a guy, and Monica and Chandler suggest one of Chandler's co-workers, Eldad (Josh Coxx). The way Chandler lovingly goes on about Eldad's attributes and how incredible he smells leaves Monica wondering whether or not he may want to date him, and not her.

They all blindside Rachel with an impromptu meeting of her prospective dates at the coffee house. The trio tries to one-up each other by demanding their contestants do things to impress Rachel. Chandler swoons over Eldad's hair and demands that he dance for Rachel. The scene gets increasingly chaotic until Eldad speaks up, agreeing with Rachel that the whole thing is embarrassing. Chandler just calmly shushes him, still intent on getting the pair set up. This scene is not just a great example of Chandler's comic timing, it also shows how well he and Monica work together as a pair ... even if they're a little more intense than Rachel would've liked. 

Dogs aren't Chandler's best friend

Season 7, Episode 8 ("The One Where Chandler Doesn't Like Dogs") is one of the series' beloved Thanksgiving specials. In this episode, Phoebe temporarily stays with the newly engaged Chandler and Monica due to an apartment fire. What her temporary roommates don't know, however, is that Phoebe has been secretly dog-sitting a pooch called Clunkers, keeping her in her room. When Monica and Chandler find out, they tell her she has to get rid of the dog due to Chandler's aggressive allergies. 

However, the truth is that Chandler has been lying about his dog allergy, and he has to confess to something that only Joey knows: Chandler hates dogs. Naturally, the group is shocked, but Chandler desperately offers an explanation, saying, "They are needy. They are jumpy. And you can't tell what they are thinking, and that scares me a little bit."

To clarify, Rachel asks if he has the same feeling towards puppies. Chandler, mortified to think there might be a puppy around, anxiously looks around for one. Everyone is surprised and appalled by this confession, including Rachel's assistant Tag (Eddie Cahill), who exclaims, "You don't like puppies?" Chandler responds that he is new, implying that Tag should stay in his lane. Chandler presents an ultimatum: Either the dog goes, or he goes. When the gang takes too long to consider their options, he throws out an impeccably delivered "Oh my Gawd!"

Chandler is no Brad Pitt

While Jennifer Aniston was married to Brad Pitt, he would often make visits to the "Friends" set in support of his wife and as a fan of the show. In the Thanksgiving episode in Season 8 (Episode 9, "The One With The Rumor"), Pitt guest stars as Rachel's high school nemesis, Will Colbert, who started the "I hate Rachel Green" club with Ross.

While running errands, Monica runs into Will and invites him to Thanksgiving dinner. The once unattractive and unpopular Will has now transformed, and as Monica puts it, "looks really good." 

There was no way to ignore Pitt's good looks, so it was addressed head-on in the episode. When introduced to Phoebe and Chandler, Phoebe thanks God for a job "well done." From across the room, Chandler quips how he would shake Will's hand, but it would be better for his ego if they didn't stand right next to each other.

As Monica and Will chat in the kitchen, they compliment each other's appearance. After Will tells her she looks stunning, Monica exclaims, "You look incredible, too. You're so fit." From the couch, Chandler yells back "I'm watching the game, but I'm not deaf." He may not take his eyes off the game, but he is very aware of the handsome man smooth-talking his wife, and this comeback is one of Chandler's best efforts.