Jennifer Aniston, Matthew Perry, David Schwimmer, Lisa Kudrow, Courteney Cox, and Matt LeBlanc in Friends

In Honor of Matthew Perry, Here Are Chandler’s Best Episodes of ‘Friends’

Matthew Perry, the actor behind Friends’ snarky but kindhearted Chandler Bing, passed away on Oct 28 after being found unresponsive in his hot tub. He was only 54 years old, and he’d spent a large portion of his life battling addictions before telling his story with refreshing honesty in his 2022 memoir.

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Perry became a superstar thanks to Friends and pulled in millions of dollars, some of which he used to fund a residential sober-living house in Malibu, helping multitudes of people battle their own substance abuse issues and, very possibly, save their lives.

Watching Friends will never quite be the same experience it used to be. Here, we look back at the Friends episodes that best showcase Perry’s talents.

The One with the Blackout (season 1, episode 7)

Matthew Perry as Chandler in Friends "The One With the Blackout" (NBC)

Only the seventh episode of Friends and Chandler was already arguably the funniest character. “The One with the Blackout” had him stuck in an ATM vestibule with Victoria’s Secret model Jill Goodacre, and it was a masterclass of awkwardness. Somehow, Perry even managed to make an inner monologue about chewing gum side-splittingly funny.

The One Where Heckles Dies (season 2, episode 3)

Matthew Perry, Matt LeBlanc and Lisa Kudrow in Friends "The One Where Heckles Dies" (NBC)

An episode that has gained a whole new poignancy after Perry’s death. “The One Where Heckles Dies” sees the Friends’ grumpy neighbor Mr. Heckles pass away and leave the contents of his apartment to “the noisy girls in the apartment above mine.” While helping clean up the clutter that “sullies the good name of crap,” Chandler discovers that he and Mr. Heckles were similar in many ways.

The episode ends with Chandler turning off the lights in the apartment and saying fondly, “Goodbye, Mr. Heckles. We’ll try to keep it down.”

The One With Chandler in a Box (season 4, episode 8)

David Schwimmer, Jennifer Aniston, Lisa Lisa Kudrow, Matt LeBlanc and Matthew Perry in Friends "The One With Chandler In A Box" (NBC)

In a moment of weakness, Chandler kisses Joey’s girlfriend Kathy, but he’s so desperate to keep his best friend in his life that he agrees to an unusual punishment. He’ll spend six hours of Thanksgiving stuck in a Chandler-shaped wooden box. If he can take it (and not make jokes), Joey will forgive him, but only then.

Can you be funny while locked in a box with only one of your fingers poking out through a hole? Matthew Perry could.

The One With All the Rugby (season 4, episode 15)

Matthew Perry and Maggie Wheeler in Friends "The One With All the Rugby" (NBC)

One for anyone who’s ever tried to shake an annoying ex. Chandler re-encounters his old flame Janice (Maggie Wheeler) and soon finds himself desperate to get rid of her. Eventually, all he manages to do is ditch her at the airport, having convinced her he’s moving to “15 Yemen Road, Yemen.”

Wheeler was one of the many Friends stars who paid tribute to Perry after his death, writing on Instagram, “What a loss. The world will miss you Matthew Perry. The joy you brought to so many in your too short lifetime will live on. I feel so very blessed by every creative moment we shared.”

The One With Ross’s Wedding (season 4, episode 24)

Matthew Perry and Courteney Cox in Friends "The One With Ross's Wedding" (NBC)

What a season finale! Ross gets as far as the altar with new girlfriend Emily, only to say the wrong name … and also, Monica and Chandler fall into bed together. Their relationship would evolve to make them into one of the best TV couples of the era, and it all happens so naturally that you can’t believe it wasn’t planned from the beginning. It was originally meant to be Monica and Joey! Can you even imagine it?

The One Where Everybody Finds Out (season 5, episode 14)

Matthew Perry and Lisa Kudrow in Friends "The One Where Everyone Finds Out" (NBC)

They don’t know that we know that they know we know! Joey, Rachel and Phoebe have all found about Monica and Chandler’s secret romance, and both groups decide to have a little fun to punish their friends for lying. It’s only Ross who doesn’t find out about Mondler until the very end, and his response is … dramatic. Don’t worry, he comes around … who wouldn’t want someone like Chandler marrying their sister?

The One With the Joke (season 6, episode 12)

Matthew Perry in Friends "The One With the Joke" (NBC)

Chandler and Matthew Perry had one character trait in common: Both of them loved to be funny. In this episode, Chandler is convinced that Ross has stolen one of his jokes and sent it to Playboy. A rift develops until both of them tell the joke to Monica, who tells them it was “offensive to women, and doctors, and monkeys.”

This episode also contains one of the sweetest Mondler moments, where Chandler tells Monica that even if everyone considers her high-maintenance, “it’s okay, because I like … maintaining you.”

The One With the Proposal (season 6, episode 24)

Courteney Cox and Matthew Perry in Friends "The One With the Proposal" (NBC)

Chandler wants to propose to Monica but there’s someone in the way … Monica’s old boyfriend, Richard (Tom Selleck.) And Chandler gets in his own way, too, by deciding to keep his proposal plans a secret from Monica. Will true love triumph in the end? Well, of course it will, but there will be some hysterically awkward situations along the way.

Perry is totally swoon-worthy during his proposal to Monica. There’s no doubt about it, he was the best boyfriend on Friends. Sorry, Joey. And not sorry, Ross.

The One With Monica and Chandler’s Wedding (season 7, episode 23)

Courteney Cox, Matt LeBlanc and Matthew Perry in Friends "The One With Monica and Chandler's Wedding" (NBC)

All through the run-up to Monica and Chandler’s big day you may have been thinking, “Will Chandler blow it? Oh, please don’t let Chandler blow it.” Good news! He didn’t blow it. He came close, but nope. By the end of the season, Chandler and Monica are wed and everyone’s happy. Well, except for Rachel, who turned out to be unexpectedly pregnant … but that’s a story for another day.

This is another episode that shows off the range of Perry’s acting talent, as he goes from poignant to hilarious at the drop of a hat.

The One With the Fertility Test (season 9, episode 21)

Matthew Perry and Courteney Cox in Friends "The One With the Fertility Test" (NBC)

Friends wasn’t always able to pull off discussion of painful real-life scenarios, but one time it did was during the Monica/Chandler arc about the two of them being unable to conceive. When Chandler tells his wife, “We’re gonna figure this out,” you believe him.

In the end, Monica and Chandler adopted two children and lived happily ever after, and despite the pain of Perry’s death, they’ll continue to live on in the minds of fans.

(featured image: NBC)

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Sarah Barrett
Sarah Barrett (she/her) is a freelance writer with The Mary Sue who has been working in journalism since 2014. She loves to write about movies, even the bad ones. (Especially the bad ones.) The Raimi Spider-Man trilogy and the Star Wars prequels changed her life in many interesting ways. She lives in one of the very, very few good parts of England.