Chandler Bing's most hilarious moments on ‘Friends’

Early in Friends, Chandler is established as one of the show’s most relatable characters. A perfect example is in season one, when New York City experiences a blackout. Chandler finds himself stuck at an ATB vestibule with model Jill Goodacre. Chandler’s inner monologue as he tries to figure out what to do is a pitch-perfect comedy, as well as telling Joey on the phone about his situation through clenched teeth and almost choking on a piece of gum. 

One of the funniest components of Chandler’s character arc is his on-and-off relationship with the irritating yet endearing Janice. In season four, he wants to break up with her but doesn’t want to deal with confrontation. He lies and tells her that his company is moving him to Yemen (the first place that pops into his head), which he now has to convince her is true. As a result, Chandler buys a ticket and is forced to actually go to Yemen as Janice waits to see his plane take off. 

In an episode quite literally titled “The One With Chandler in a Box," Chandler lies down in a wooden box for six hours to earn Joey’s forgiveness after kissing his girlfriend Kathy. Even though he is not visible on screen for half the episode, his presence is felt throughout, as he points his fingers out to make motions to the group. While the notion is, of course, silly and far-fetched, Chandler’s commitment proves how much he cares about Joey.

In another situation where Chandler doesn’t have the guts to break up with someone, he finds himself at Bloomingdale's with Joanna, Rachel’s boss. Joanna handcuffs a half-naked Chandler to a chair in her office and leaves him there while she goes to a meeting. Rachel finds him and relocates him to a filing cabinet. As he tries to break free, he pulls the cabinet towards him and is smacked in the head. The scene is a brilliant showcase of Perry’s physical comedy skills.

Chandler struggles to quit smoking and uses a hypnosis tape. Because the tape is from Rachel’s friend, the voice on it repeats the mantra that he is a “strong, confident woman." This doesn’t just help Chandler quit but also embrace his more feminine side. He hilariously comes out of the shower wearing a towel around his chest and wrapped over his head. The icing on the cake is Joey finding the tape and recording over it, requesting Chandler make him a cheese sandwich every day and buy him hundreds of dollars worth of pants. 

Chandler’s a great guy, but he can definitely be careless. After breaking up with Janice, Chandler gets drunk and fools around with Joey’s sister, Mary Angela, at his birthday party. However, all seven of Joey’s sisters look similar, and Chandler can’t remember which one Mary Angela is. At the Tribbiani family dinner, Chandler tries to identify her. Chaos ensues when he kisses the wrong sister, and Joey tells him to apologize to Mary Angela. However, he still can’t remember which one she is.

In season two, Julia Roberts guest stars as Susie, whom Chandler humiliated at school. Chandler and Susie start dating until Susie gets her revenge. Out for dinner, she makes him put on her panties, takes his clothes, and leaves him in the bathroom stall. Things get more chaotic when Ross and Joey enter the bathroom and look down at the scene from the surrounding cubicles, and a man walks in to witness this. Chandler is forced to walk out of the restaurant naked, with only the unhinged cubicle door covering him. 

When Chandler and Monica become engaged, they organize engagement photos. While Chandler is always laughing and grinning, it turns out he cannot smile in front of a camera. Instead, Chandler either has his teeth clenched or looks like he is in some sort of pain. Joey tries to teach him to smile on cue, but that doesn’t work. In the end, nothing can make him smile properly, and Joey ends up standing in for him in his engagement photos. 

Chandler's workplace is a key feature in Friends, including the fact that no one actually knows what he does there. Chandler’s coworker Bob called him Toby, but Chandler didn’t correct him because he wanted a donut. Years have now passed, and it’s too late to correct Bob. This proves to be a problem when Bob asks Toby/Chandler to get revenge on a guy called Chandler, who has prevented him from getting a promotion. Chandler has no choice but to go along with this and even helps Bob destroy his own office. 

When Chandler and Monica first start dating, they do everything they can to keep their romance secret from the group. However, Chandler slips up and unintentionally kisses Monica in front of Rachel and Phoebe. To avoid suspicion, what does he do? Kiss Rachel and Phoebe to make it less awkward, not that it works at all. Monica says it’s probably some European thing he picked up in London, while Chandler insists he was just trying to bring some culture to the group. 

In season eight, Chandler discovers the relaxation of taking a bath. Adamant that he doesn’t like them, his mind is changed when Monica draws one for him, complete with bubbles, candles, and Enya’s “Who Can Say." Chandler soon becomes addicted to baths and even steals the bath Monica has prepared for herself. What Chandler doesn’t expect, however, is when the group gathers in the bathroom while he is in the tub, as they gush over the news of Rachel and Ross having a girl. It is a little overcrowded, to say the least.

One of the most iconic Friends scenes is when Chandler, Rachel, and Ross try to lift Ross’s new couch up the staircase. Ross repeatedly yells “PIVOT!” with emphatic pronunciation as the three try to navigate the stairs. Ross’s yelling is met with Chandler angrily screaming, “Shut up, shut up, SHUT UP!” It’s one of the show’s most hilarious and over-the-top moments, quoted by fans around the world and always appearing on "best of" lists like this one. 

Even within the first ten minutes of the pilot episode of Friends, Perry establishes Chandler’s iconic wit and sarcasm that he is so well known for. The gang is at the coffee house when a sulking Ross says he just wants to be married again. As if summoning this, Rachel walks in wearing a wedding dress after leaving Barry at the altar. Chandler then comments, “And I just want a million dollars!” in response to the coincidence, and it is one of his best lines.

Highly regarded as one of the best Friends episodes of all time, “The One Where Everybody Finds Out” sees Rachel and Phoebe try to mess with Monica and Chandler to get them to reveal they are dating. However, Monica and Chandler know they know about their relationship and go head-to-head to see which side will admit it first. It goes so far that Phoebe and Chandler try to seduce each other and even kiss before Chandler stops and confesses that he is in love with Monica.  

The relationship between Chandler and Joey is one of the best elements of Friends, and while Chandler loves Joey, he too is often confounded by his lack of intelligence. In season five, the gang finds themselves trapped in Monica’s bedroom once again, where they previously hid when Ross and Rachel were fighting. Joey reveals his box of supplies for the long haul, and Chandler notices he has condoms. Joey says they may have to repopulate the earth, with Chandler hilariously replying, “And condoms are the way to do that?”

Even if Chandler isn’t the specific focus of a scene, his one-liners help him steal the show. In the final season, Ross decides to go to the tanning place Monica also goes to but fails to follow the instructions and comes home a little too tanned. When Ross shares where he went, Chandler responds, “Was that place… THE SUN?” Perry’s comedic timing and line delivery elevate what could have been a throwaway joke to a hilariously memorable reaction and exchange. 

Friends features several flashback episodes as the characters reminisce about their younger years. A couple of those episodes go back to when Chandler and Ross were in college, sporting some seriously wacky ‘80s looks. However, Chandler’s A Flock of Seagulls-inspired hairdo absolutely earns all the laughs. ‘80s Chandler is not the present version we know and love and is evidently more shallow as he calls Monica fat. However, should he really be talking with that cut? 

There were multiple Christmas-themed episodes during the run of Friends, and one of the most talked about is “The One With The Holiday Armadillo.” Ross is taking care of Ben over the holidays, and to teach him about Hanukkah, he dresses up as the Holiday Armadillo — until he is upstaged by Chandler’s Santa Claus. While Chandler initially arrives to help Ross out, Ben is more keen on Santa, and a rivalry between Mr. Claus and the Holiday Armadillo is born.

In season seven, fans were given an episode focusing on the barely explored dynamic between Chandler and Rachel. When a cheesecake is accidentally delivered to the wrong apartment, the pair eat it and become addicted. When another cheesecake shows up a couple of days later, they can’t help themselves again. Chandler and Rachel become so obsessed with this cheesecake that they eat any salvageable remnants off the floor when it falls to the ground. That must be one good cheesecake. 

Although Joey is Chandler’s roommate throughout most of the series, there is a time when he moves out. That’s when we meet Eddie, who at first seems like a regular guy. However, his behavior starts to become more erratic, and Chandler realizes something is not quite right with him. He accuses Chandler of having an affair and killing his goldfish, believes they took a trip to Vegas that never happened, and watches him sleep at night. This is the last straw for Chandler.