15 Funniest Chandler Bing Moments on Friends

One of television’s most successful and beloved series, Friends, achieved that status for numerous reasons. One of these myriad reasons would be the impeccable chemistry of its cast.

Although each actor and character left an indelible mark on the series, many fans call Chandler Bing their favorite. Thanks to Matthew Perry’s comedic timing and natural charisma, he created one of the most iconic characters in television history.

A list of funniest moments could go on forever, so highlighting the most hilarious represents a masterclass in physical, witty, and sarcastic comedy.

1. Chandler Is Trapped in an ATM Vestibule With Jill Goodacre (Season 1, Episode 7, “The One With the Blackout”)

The season one classic “The One With the Blackout” features many hilarious, memorable moments, but none more so than Chandler getting trapped in an ATM vestibule with the model Jill Goodacre. No single moment or line stands out because the entire sequence throughout the episode is golden.

From his inner monologue to his phone call with Joey and nearly choking on gum, these scenes showcase Perry’s array of talents and comedic abilities. The episode also gave us the iconic line that many will say when offered a piece of gum: “Gum would be perfection.”

2. Chandler and Phoebe Pretending To Seduce Each Other (Season 5, Episode 14, “The One Where Everybody Finds Out”)

Chandler and Monica (Courteney Cox) hiding their relationship from their friends in season five gave viewers many funny moments and brought a refreshing new dynamic to the series. The hilarity comes to a head when Phoebe and Chandler attempt to make each other crack by pretending to be romantically interested. Or, as Chandler would say, “The mess-ers become the mess-ees.”

Both actors make the scene incredible, but Perry, in particular, makes us laugh with his awkward expressions, mannerisms, and inability to kiss Phoebe. Of course, that’s when one of his funniest moments turns into one of the sweetest when he declares that he loves Monica.

3. Chandler Kisses All Three Women (Season 5, Episode 2, “The One With All the Kissing”)

Early on in season five, Chandler quickly has to improvise when he kisses Monica goodbye without thinking. He then kisses Rachel (Jennifer Aniston) and Phoebe (Lisa Kudrow), something he does the next time he says goodbye to them. Monica improvises, too, saying he must have picked up a European custom while in London.

His forward, quick thinking made the audience erupt with laughter, especially his saunter out saying, “Always a pleasure.” Such a scene only works because of Perry’s timing, making a potentially off-putting moment hilarious.

4. Chandler Can’t Smile (Season 7, Episode 5, “The One With the Engagement Picture”)

Taking pictures fills so many people with dread, but none more so than Chandler Bing. The ordinarily jovial guy becomes a bundle of tension when he and Monica attempt to take engagement photos.

As soon as the camera appears, Chandler loses all ability to smile naturally. Instead, he makes awkward, even scary, expressions, trying to form a smile. As Perry contorts his face, viewers can’t help but laugh and maybe even relate. After all, sometimes the funniest moments come from shared experiences.

5. A Friendly Competition (Season 4, Episode 12, “The One With the Embryos”)

Much like the scenes from “The One With the Blackout,” Chandler’s funniest moment in “The One With the Embryos” cannot be condensed into a single one. Rather, the entirety of the game between Chandler, Joey, Rachel, and Monica has become seminal in the series.

These actors bring out the best in each other, so the back-and-forth and intensity of the “friendly” competition make it laugh-out-loud funny. From Chandler’s excited and nervous hopping before the lightning round to his exclamation, “Nice shooting,” after Joey remembers Ross and Monica’s grandmother’s name, viewers no doubt have sore cheeks from smiling so much.

6. “You Have To Stop the Q-Tip When There’s Resistance.” (Season 2, Episode 1, “The One With Ross’s New Girlfriend”)

Perry became known for improvisation in the occasional scene from very early on. So, in tune with his character, these moments never felt out of place or out of character. Indeed, they feel completely natural and always bring laughs.

The best one comes when Joey can’t remember when he first began seeing a tailor, rambling between different ages and then asking, “When was 1990?” Perry came up with a sarcastic zinger on the spot: “You have to stop the Q-tip when there’s resistance,” alluding to the fact that Joey’s incoherence must be a result of brain damage.

Perry does not miss a beat, putting his finger in an invisible holster, knowing from the audience’s laughter that he nailed the joke. It became one of Chandler’s most memorable quotes, demonstrating how no one else could make the character as funny as Perry could.

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

Sometimes, little moments can surprise viewers out of nowhere and result in side-splitting laughter. A perfect example would be Chandler’s hilariously awful imitation of a whip.

In trying to make fun of Ross about being whipped, he becomes the one they all laugh at with his exaggerated movements and enthusiastic “Wappah.” The funniest part remains his lack of awareness about how bad it is, even when Joey points it out. No wonder Joey tells him, “You can’t do anything!”

8. Chandler’s New Year’s Resolution (Season 5, Episode 11, “The One With All the Resolutions”)

Being unable to tell jokes at his friends’ expense proves to be a challenging New Year’s resolution for Chandler in season five. It would be difficult under any circumstances because his wit and sarcasm come as easily to him as breathing.

His friends make it very difficult Ross goes on a date with a woman with an amusing last name and buys leather pants, and Phoebe tries to teach Joey guitar using hilarious hand shapes instead of chord names.

The only debatable thing that remains is what’s funnier: the way Chandler must resist, looking like he’s in physical pain holding back, or when he can’t take it anymore and tells them all off at once? Either way, it gives viewers plenty to delight in.

9. Chandler Gets Mad at Joey for Wearing His Clothes (Season 3, Episode 2, “The One Where No One’s Ready”)

Chock full of hilarious moments, many fans consider “The One Where No One’s Ready” one of the show’s greatest episodes. Chandler and Joey bicker throughout, coming to a head when Joey (Matt LeBlanc) retaliates in the silliest way imaginable to Chandler supposedly hiding his underwear.

Joey comes in wearing all Chandler’s clothes, ticking Chandler off. However, learning Joey has gone “commando” elicits the hilarious reaction of absolute anger and disgust, creating an iconic moment for both actors.

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

In “The One Where Chandler Can’t Cry,” his friends can’t believe his inability to cry at certain things like sad movies, photos from childhood, or even the inevitability of a loved one’s death. Instead, Chandler gives them his typical sarcastic comebacks, such as “Yes, it was very sad when they stopped drawing the deer,” when Bambi’s mother dies.

Of course, not even Chandler can be sarcastic all the time. The floodgates finally open when he watches an exchange between Ross (David Schwimmer) and Rachel, wondering why they can’t work things out. Punctuating this tender moment with humor proves to be brilliant.

11. Chandler Pretends To Move to Yemen (Season 4, Episode 15, “The One With All the Rugby”)

No relationship (besides Chandler and Monica) gave viewers as many laugh-out-loud moments as the romantic saga of Chandler and Janice (Maggie Wheeler). When this lovably annoying girlfriend comes back into his life, he can’t find a way to break up with her. So, he lies and says his company has transferred him to Yemen.

Unable to get the airport staff to go along with his ruse, Chandler must buy a ticket and board the plane, amusingly asking a lady if he can stay with her. Perry makes the scene funnier with his resigned expression and desperation in his voice. We wonder how many letters Janice wrote to 15 Yemen Road, Yemen.

12. Chandler Sings David Bowie (Season 5, Episode 19, “The One Where Ross Can’t Flirt”)

The Friends cast does not get enough credit for their pratfalls and physical comedy. Perry had the ability to make viewers bust a gut laughing with his over-the-top and silly running, dancing, falling, and other stunts.

In “The One Where Ross Can’t Flirt,” audiences see all of his talents on full display. Still, the last moments bring the most humor with a videotape that suddenly has Chandler singing David Bowie’s song “Space Oddity” on it. He then leaps over the couch with vigor to stop and retrieve the tape. He makes the quick, agile moment so funny and appear so effortless.

13. Chandler, Rachel, and Phoebe Find Christmas Gifts (Season 6, Episode 10, “The One With the Routine”)

Speaking of physical comedy, in “The One With the Routine,” Perry demonstrates Chandler’s insecurities, fears, and penchant for exaggerated movements all in one fell swoop.

When searching for Monica’s Christmas gifts, Chandler expresses horror that Rachel and Phoebe have seen something he keeps hidden in the back of his closet. Hilariously, he snaps his fingers and says, “That just didn’t happen,” as if the gesture magically turns back time.

These small things showcase how much Perry honed his craft to create a fully fleshed-out character. Little quirks and details make up a person. This moment endears Chandler to the audience as they laugh.

14. Chandler Sings Show Tunes (Season 8, Episode 17, “The One With the Tea Leaves”)

Small moments frequently become fan favorites. Chandler singing show tunes proves to be a perfect example. It also furthers a running joke about Chandler’s less-than-typically masculine taste.

As he, Monica, and Rachel organize CDs, he begins singing “Tomorrow” from Annie with carefree glee. When he notices their reaction, he ends his singing with a deeper, more serious sound. Of course, his attempt at appearing more macho makes viewers laugh because it rings false. Still, we wouldn’t change him for the world.

15. “Shut Up, Shut Up, Shut Up!” (Season 5, Episode 16, “The One With the Cop”)

Any diehard Friends fan cannot hear the word “Pivot” without thinking and laughing about this infamous season five scene. As Ross, Chandler, and Rachel attempt to move Ross’s new couch up to his apartment, Ross thinks shouting “Pivot” over and over will help. It doesn’t.

As hilarious as Schwimmer makes the scene, Perry yelling “Shut up” three times perfects it. Often replicated but never duplicated, one of the most iconic moments of the series would not be as funny without Perry’s presence and immense talent.