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Friends - Chandler Bing's top 10 funniest moments

29 Oct 2023

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After the devastating news of the passing of Matthew Perry, aged 54, we take a look through 10 of his funniest moments as his most iconic character, Chandler Bing.

10. Trapped in an ATM vestibule ("The One with the Blackout")

Yes, Chandler, it's a vestibule. Not an atrium. A vestibule. Jill Goodacre says so. When he's stuck in one alongside the model during a New York City blackout, it's perhaps the best blackout experience anyone has ever had. His muffled assessment of the situation to the other friends is particularly memorable, while his failure with his chewing gum provides some excellent physical comedy. Fortunately for us, we don't need that security tape.

9. Joey's tailor ("The One with Ross's New Girlfriend")

Chandler rued the day he asked advice on where to get pants altered. He goes to Frankie, the long-time Tribbiani tailor, where he cracks a joke about keeping the cuffs "only as long as I have the pants" before being, er, cupped. When he returns home, he's on edge and furious at Joey for sending him to such a man, and is astounded when Joey suggests it's how they do pants. His expressions as Joey realises the truth are fantastic and, grim as it is for the character, those reactions are priceless.

8. Failed proposal to Monica ("The One with the Girl Who Hits Joey")

The group all know of Chandler and Monica's relationship, and begin to make jokes about their future as a couple, which triggers Chandler's commitment fight or flight. It causes a rift in their relationship and so on Joey's advice of making a big gesture, Chandler does the obvious thing: propose to Monica in front of everyone. It's so funny to see the sudden nature of his change of mindset, explaining he doesn't know why he's doing it but that he's not scared to, and that he's sorry (the fourth-best reason to get married - "The best reason... is pregnancy"). It's just a relief she doesn't say yes and cause him to make a Chandler-shaped hole in the door.

7. Dressing up as Santa ("The One with the Holiday Armadillo")

Chandler's a great friend. Ross, in trying to teach Ben about Hannukah, doesn't plan to dress up as Santa and when his son guilts him into it on December 23, he's out of luck, and forced to dress as the mythical Holday Armadillo. But Chandler comes through, borrowing a Saint Nick costume from a colleague. He's sad when sent away without getting to "shake my belly like a bowl full of jelly" and after failing to subtly hand Ben money while shaking his hand. It's a great sight and sweet too when he offers to stay provided Ben learns about Hannukah. An iconic Easter Bunny funeral.

6. Reaction to being robbed ("The One with the Cat")

When Joey and Chandler try to sell the entertainment centre, the pair end up being robbed as Joey gets himself trapped inside it by a prospective buyer. Chandler's initial stunned reaction diffuses the seriousness of it - the visual gag of him arriving home and throwing his keys on the table, only for them to land on the floor, is great; so too is his suggestion that if Joey sees the guy again, he will simply "Bend over?!" - but his more considered assessment later is the real gem. "Joey was born, and then 28 years later, I was robbed!" Still, at least he didn't take the five of spades.

5. The cheesecake ("The One with All the Cheesecakes")

"We don't want her to come back to bad cheesecake." That's the justification for Chandler and Rachel stealing the second of Mrs. Braverman's cheesecakes, and he's as funny as the dessert is delicious. He initially tries to save it by hoping Mama's Little Baker is a cheesecake conglomerate (it is not), then struggles to say goodbye to another cake, before later observing that the pair just don't pay for food any more having gone for lunch. But it's his argument over splitting the last cake which stands out, his attempt to measure the halves preceding a magnificently dramatic surprised face at Rachel dropping hers. That the pair end by scraping bites off the floor only adds to the hilarity.

4. Dealing with Eddie ("The One Where Eddie Won't Go")

After Joey moves out to a fancy, high-end apartment, Chandler gets a new roommate, Eddie (Adam Goldberg). But Eddie's slightly crazy and Chandler wants rid of him when he sees Eddie watching him while he sleeps. His disbelief at that is hilarious - "Where did you hear it from before?!" when Eddie says he wants to hear it from Chandler's lips - but so too are his reactions when Eddie later dehydrates fruit and brings a mannequin head for a cocktail party. Chandler's straight-faced ruse that Joey's always lived there is the thing which makes Eddie leave, and the thing which solidifies this as one of Chandler's great moments.

3. Trapped in the toilet ("The One After the Superbowl, Part 2")

When Chandler meets former schoolmate Susie (Julia Roberts), he thinks he's found the perfect woman: they flirt, she asks him to do it in an elevator; it's true love. But their dating is just an elaborate ruse for her to embarrass him as revenge for him lifting her skirt in school. So she has him wear her underwear, then steals his clothes in a restaurant toilet. The humiliating moment when Joey and Ross both come in and see him exposed is hilarious, Chandler joining in on Joey's whistling, then having to ashamedly front up and beg for their underwear, before graciously exiting the restaurant using the toilet door to shield himself.

2. The chair ("The One Where No One's Ready")

Ask 100 Friends fans their favourite episode and a fair few will suggest this. Joey and Chandler's fight over use of a chair in Monica and Rachel's apartment is so stupid and yet so hysterically funny, and while it's Joey's "Could I be wearing any more clothes?" which stand out, Chandler is a gem here. His desperate run to pounce on the loose chair - which caused Matt LeBlanc to dislocate his shoulder - his shout of "He took my essence" after stealing Joey's underwear, and his involvement in the glass of fat. It's an absolute hoot.

1. Monica and the maid ("The One with the Stain")

When Chandler hires a maid to clean the apartment, it sits uncomfortably with Monica, who doesn't like to relinquish control. But it's especially so once she believes that Brenda (Arden Myrin) has stolen some of her clothes. For 10 seasons of Chandler one-liners, this episode has the most consistently funniest, from his blank-faced "What?" when Monica first suggests the theft to his "I fear a jury will see it the same way" when she says they're in this together. His dramatic "No" when told to take a look at Brenda's bra has always been a personal favourite too. This episode isn't Chandler-focused but it is the show's best exhibition of Perry's comic timing.

Rest in peace, Matthew Perry.