The Best of Chandler Bing: Matthew Perry’s 15 Funniest Friends Episodes

Our very own Chandler Bing is no more. Matthew Perry tragically passed away on Saturday at the age of 54, leaving his fans in a state of shock and pain.

Matthew Perry gave us many memorable performances in TV and film over the years, but there’s no denying he’ll be best remembered for one role in particular: that of Chandler Bing on Friends. He was a virtually unknown when Friends debuted on NBC in 1994. However, he quickly rocketed to stardom by crafting one of the most iconic comedy performances in TV history.

Chandler was smart and funny and one of the most iconic sarcastic characters in television history. In honor of Matthew Perry’s life and career, let’s examine the 15 Funniest Chandler Bing Episodes.

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

I am stuck in an ATM vestibule with Jill Goodacre.” We all remember the famous line. Season 1, Episode 7: “The One with the Blackout”

Perry’s exaggerated, comedic facial expressions are the star in this early Friends episode, which finds Chandler trapped in an ATM vestibule with Victoria’s Secret model Jill Goodacre during a New York City blackout.

Much of the episode features Chandler’s inner monologue via a self-deprecating voiceover from Perry, and damn if it isn’t always hilarious. I still reply, “Gum would be perfection,” whenever someone offers me a stick.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Matthew Perry and Jill Goodacre in Friends | Source: IMDb

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

I can’t remember which sister.” We all cracked up when we first watched this scene. Still somewhat in shock that his ex Janice (Maggie Wheeler) is married with a child on the way, Chandler drowns his sorrows in Jell-o shots at Joey’s birthday party and ends up fooling around with one of Joey’s sisters.

The funny part is he can’t remember the sister. He takes Ross’s assistance to go to the Tribbiani house in hopes of figuring out which one Is Mary Angela, the sister he made out with.

He has some great lines here and probably deserved the punch to the face delivered by the toughest of Joey’s sisters, Cookie.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Alex Meneses in Friends | Source: IMDb

3. “The One After the Super Bowl, Part 2” (Season 2, Episode 13)

Matthew Perry worked opposite yet another gorgeous guest star the very next season: Julia Roberts, who plays a former classmate of Chandler’s. The fans were more excited for the episode since Matthew Perry was rumored to be dating Julia Roberts then.

Chandler initially dreams of having a shot with his former friend. However, she was seeking revenge on him for humiliating her in the fourth grade.

Cue the classic sitcom prank: The woman steals the man’s clothes. Perry flailing around naked in that bathroom stall remains one of the series’ most iconic scenes and proof that his physical comedy was just as hilarious as his dry delivery.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Matt LeBlanc, Matthew Perry, and David Schwimmer in Friends | Source: IMDb

4. “The One Where Everyone Finds Out” (Season 5, Episode 14)

“I am in love with Monica,” Chandler said these lines for the first time in this episode, and we all fell in love with Mondler. One of the funniest Friends episodes, highlighted by the “They don’t know that we know that they know we know,” continues to make the fans laugh out loud.

When Phoebe sees Monica and Chandler “doing it,” the whole Messer vs. Messee game begins, leading to some hilariously awkward interactions between Phoebe and Chandler. Kudrow is fantastic in this episode, but so is Perry, especially when he invites Phoebe over to “feel his bicep… and maybe more.”

Chandler’s awkwardness when he says, “It’s very nice,” referring to Phoebe’s bra, along with “I’m very excited we’re going to have all the sex,” makes this one of Chandler’s best episodes.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Top 15 Funniest Friends Episodes for Chandler Bing Fans | Source: IMDb

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

The Yemen Episode Guys!!

Chandler’s on-and-off romance with nasal Noo Yawker Janice brought out the best in Perry, and he hit new heights. As Chandler was so desperate to break things off with her, he made up an elaborate lie about being transferred to Yemen for work.

Perry made Chandler’s dilemma hilariously agonizing as he went to ridiculous lengths to keep the lie alive, even buying a ticket to Yemen and boarding the plane so Janice wouldn’t catch on. It’s still worth it, though.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Jennifer Aniston and Matthew Perry in Friends | Source: IMDb

6. “The One with the Cuffs” (Season 4, Episode 3)

Perry once again proves himself to be the master of timing and facial expressions in the episode where he dates Rachel’s boss and ends up hand-cuffed to the desk in her office.

It’s a rare but welcome Chandler-and-Rachel episode. Perry and Aniston play off each other perfectly, with an easy back-and-forth. Perry’s look of disbelief after hitting his head with the file cabinet remains one of my favorite series jokes.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Matthew Perry in Friends | Source: IMDb

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

Monica decides she and Chandler should have their engagement photo in the newspaper. She discovers that Chandler is not very photogenic, and that’s putting it kindly.

Even when he’s smiling or laughing naturally, as soon as the camera clicks, his smile morphs into a hilarious grimace. It’s some of the best physical comedy showcased by Perry throughout Friends’ 10-year run. It’s impossible not to laugh at his “smile” in the photos, even as many times as it happens throughout this episode.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Jennifer Aniston, Lisa Kudrow, and Matthew Perry in Friends | Source: IMDb

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

He played Chandler Bing for a decade, but Perry proved he could still surprise us in this installment, with Chandler developing a taste for luxurious bubble baths.

The sight of him unwinding to the gentle sounds of Enya was a delight, and it hilariously culminated in the rest of the gang invading the bathroom and interrupting his bliss. Even late in the series’ run, Perry still had his comedy fastball, and in our hearts, he always will.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, Matthew Perry, and David Schwimmer in Friends | Source: IMDb

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

Monica hosts a Halloween party and gets Chandler a pink bunny costume. The first moment you see him as a big fluffy pink bunny is hilarious. Monica, on the other hand, looks fantastic as Catwoman, but when doesn’t she? She’s the one who picked the costume for Chandler and claimed she couldn’t find anything other than a pink bunny. “It was the pink bunny or no bunny at all,” she tells him.

“Always no bunny at all!” he responds in his usual deadpan voice. When Ross shows up dressed as “Spudnik,” a potato and satellite, naturally, Chandler makes his classic jokes about how he looks like a doody, saying later that Ross looks “a little flushed.” The arm-wrestling match between Ross and Chandler is epic, and the way Chandler still tries to prove himself to Monica repeatedly is so sweet.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Courteney Cox and Matthew Perry in Friends | Source: IMDb

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

Though the season-ending engagement with Monica is always a goodie, this one is also a fantastic use of Perry’s wit and impeccable comedic timing.

When Monica finds out he hasn’t cried since childhood, she becomes desperate to find something that will make him tear up. One of his best lines comes in this episode: “Well, that makes me feel warm inside my cold tin chest.”

Finally, he sheds his first tears in decades when he gets sad that Ross and Rachel can’t ever seem to make it work between them, even though it’s so clear to everyone that they’re meant to be together.

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

Chandler’s vulnerable side comes into play in this Season 2 Episode when the cranky neighbor, Mr. Heckles, dies suddenly, leaving the girls all his belongings.

When the gang is cleaning up the mess in his apartment, Chandler discovers the similarities he has with Mr. Heckles. He realizes they were both voted Class Clown, and they both turned down several attractive women because of minor flaws, like prominent gums or, in Chandler’s case, large nostrils. Chandler starts panicking that he will die alone, just like Mr. Heckles.

He can make his way in the world. He even dates a woman from his office whom he’s avoided asking out before because of her large head. The credits scene, though, is hilarious when he thinks his head looks like a golf ball next to hers. Classic Chandler.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Jennifer Aniston, Lisa Kudrow, Matt LeBlanc, Matthew Perry, and David Schwimmer in Friends | Source: IMDb

12. “The One Where Chandler Crosses the Line” (Season 4, Episode 7)

One of Chandler’s best pre-Monica romantic sparks was with Kathy, Joey’s actress girlfriend, played by Paget Brewster. Chandler’s secret yearning for his best friend’s girl was wrong, of course, but also understandable, and the scenes where Chandler wrestled with his true feelings proved that Perry could be a more than capable romantic lead.

(The next episode, with Chandler spending Thanksgiving in a box as penance, also showed that we didn’t even need to see Perry’s face or body for him to make us laugh.)

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Matthew Perry and Paget Brewster in Friends | Source: IMDb

13. “The One with the Thanksgiving Flashbacks” (Season 5, Episode 8)

You got to love the Friends episodes that mock ’80s fashion, and Chandler’s “flock of seagulls” hairdo, this Thanksgiving flashbacks episode might take the cake. But it’s also such a treat for Chandler fans to see some backstory for his character, including a rude comment he once made about Monica.

Don’t worry, he apologizes, and we even get the sweet moment when Chandler tells Monica he loves her for the first time.

14. “The One After Ross Says Rachel” (Season 5, Episode 1)

Any Monica-and-Chandler lover knows that Season 5 of Friends is the season. It’s the season of the sexy secret! It all starts with this season premiere, which finds these two new lovebirds desperate for privacy during their last few hours in London because London is the only place they are “allowed” to hook up.

But after it becomes clear how badly they both want, they decide to keep the excellent sex going, eventually blossoming into arguably one of the greatest romances in sitcom history. The chemistry between Perry and Cox just can’t be beat.

Chandler’s freaky expressions and one liners made sure this remains one of the funniest Chandler Bing Episodes.

Top 15 Funniest Friends Episodes for Chandler Bing Fans
Jennifer Aniston and David Schwimmer in Friends | Source: IMDb

15. “The One with the Proposal: Part 2” (Season 6, Episode 25)

Every once in a while, the Friends got to display their dramatic chops as actors. Nowhere did Perry do that better than in the heartfelt, tear-jerker Season 6 finale, where Monica proposes to Chandler.

Both Perry and Cox will break your heart with their genuine tears as Chandler stammers out why he wants to spend the rest of his life with Monica. Only cold-hearted robots won’t cry watching it.

Watch F.R.I.E.N.D.S on:
Top 15 Funniest Friends Episodes for Chandler Bing Fans
Tom Selleck, Courteney Cox, and Matthew Perry in Friends | Source: IMDb

16. About FRIENDS

Friends is an American television sitcom created by David Crane and Marta Kauffman, which aired on NBC from September 22, 1994, to May 6, 2004, lasting ten seasons. With an ensemble cast starring Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, Matthew Perry and David Schwimmer, the show revolves around six friends in their 20s and 30s who live in Manhattan, New York City. The original executive producers were Kevin S. Bright, Kauffman, and Crane.

FRIENDS stars David Schwimmer, Jennifer Aniston, Courteney Cox, Matt LeBlanc, Matthew Perry, and Lisa Kudrow.


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