Remembering Matthew Perry: The Actor's 10 Best Episodes on 'Friends'

An ode to an iconic character played by an incomparable actor, here are Matthew Perry's 10 best episodes as Chandler Bing on 'Friends.'

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Matthew Perry’s legacy precedes itself. 

The incomparable comedian touched the hearts of audiences worldwide through his portrayal of Chandler Bing in the widely loved sitcom Friends, and his tragic passing has sent shockwaves across the world. Fans have poured their tributes on social media, remembering some of the actor’s best moments both on the show and off it as an outspoken advocate, inspiration, and friend to more people than he could ever count. 

We all loved Friends. And we all particularly loved Chandler Bing. Perry managed to make the character his own and then some, with his unmatched talent shining through each episode and making Chandler one of the most iconic fixtures of pop culture. Although there are at least 50 more, we’ve rounded up Chandler’s 10 best episodes in Friends to celebrate the late actor’s infinite legacy. He will always be remembered. 

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

One of Friends’ earlier episodes, “The One with the Blackout” sees the gang dealing with a city-wide power cut, and no one enjoys it more than Chandler. While the rest of the crew are chilling at Monica’s (Courteney Cox) apartment, Chandler serendipitously gets stuck in an ATM with none other than Victoria’s Secret model Jill Goodacre. The tight four corners of the ATM paired with Chandler’s dream girl make for comedic goodness, with our namesake king of cringe struggling to impress Jill any way he can. From choking on gum to winning the night with a sheepish kiss on the cheek, Perry displays his comedic deftness in this episode and cements the charisma that we were all going to fall in love with in later seasons.  

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

Awkward hookups always make for great comedy, but hooking up with one of your best friend’s sisters and not remembering which one makes for even greater comedy. In this Season 3 episode, Chandler gets a wee bit too drunk at Joey’s (Matt LeBlanc) birthday party and fools around with one of his seven sisters, Mary Angela. To calm an upset Joey, Chandler tricks his friend into believing that he’s really falling for Mary Angela and that their steamy session wasn’t in vain. The gag? Chandler can’t remember which one of the sisters is Mary Angela, and proceeds to go through the most painstakingly awkward attempt at redeeming himself. It’s hilarious. It’s Chandler’s awkwardness at its absolute best. And he deserved that punch from Cookie in the end.  

3. “The One With the ‘Cuffs” (Season 4, Episode 3) 

An absolute staple of Friends is seeing the crew get caught up in hilariously awkward situations with no way out. From Ross’ (David Schwimmer) leather pants fiasco to Rachel’s (Jennifer Aniston) bombed job interview, there isn’t something these guys haven’t been through, but no one has it worse than Chandler. One of the best Chandler-gets-stuck-half-naked-somewhere episodes, and yes there’s quite a few of them, this Season 4 episode sees Chandler getting stuck in Rachel’s boss’ office. He’s cuffed to her chair. He’s half naked. He’s regretting the day he ever laid eyes on this woman. And Rachel brilliantly makes it all the worse for him. Chandler and Rachel are arguably Friends’ unsung duo, and this episode proves it and then some. 

4. “The One With Chandler in a Box” (Season 4, Episode 8) 

Friends has a slew of memorable Thanksgiving episodes, but “The One With Chandler in a Box” takes the cake for Bing’s best holiday extravaganza. After Chandler mistakenly pursues Joey’s new flame, he tries to make amends by spending six hours in a box (as per Joey’s orders of course). Putting one of your characters in a box and keeping them there for an episode’s entirety is a wild premise, but when you have someone like Matthew Perry taking on the baton, it becomes entirely plausible and all too hilarious. Perry manages to still steal every scene he’s in in that episode, even while tucked away in the box’s four corners, and arguably delivers its best moments. His ability to still captivate despite not lucidly being onscreen is a testament to his unmatched charisma and comedy, and makes this episode one of his most memorable. 

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

Perhaps my personal favorite episode of Friends, “The One With the Embryos” sees Chandler and Joey teaming up against Monica and Rachel to win over their apartment through a trivia competition. The game itself is absolutely hilarious and we get to learn the wildest facts about the foursome, like who Joey’s imaginary friend is, and while the gang seems to know each other pretty well, everything comes crashing down when the girls are asked to explain Chandler’s job. A running gag throughout Friends, Chandler’s job has remained a mystery, and this scene beautifully tributes the age-old joke. While the girls’ losing moment is hilarious, it’s made even funnier with Perry’s reaction to the scene and his incomparable sarcasm throughout the entire episode. 

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

To explain why this episode is so iconic, all I have to say is: “15 Yemen Road Yemen.” One of Chandler’s most iconic one-liners, this Season 4 episode sees Chandler reluctantly reuniting with Janice (Maggie Wheeler) and doing everything he can to get her off his back. His solution? Telling Janice that he’s moving to Yemen for work, a carefully thought out plan, if you ask us, that not-so-surprisingly fails when Janice decides to be with him until his very last day in New York. Chandler goes to extreme lengths to see his lie through, and Perry’s comedic chemistry with Wheeler is an absolute joy to watch in this episode particularly. 

7. “The One Where Everybody Finds Out” (Season 5, Episode 14) 

“The One Where Everybody Finds Out” is not only one of Chandler’s best episodes, but one of Friends’ best episodes—period. The iconic Season 5 episode sees the whole gang finding out about Monica and Chandler’s secret affair, and the entire cast is at the top of their game in this one especially. From Phoebe's (Lisa Kudrow) bellowing “My eyes!” to the ever so iconic “They don’t know that we know that they know,” the episode helms some of Friends’ most hilarious moments, and it all comes together in the scene where Phoebe tries to seduce Chandler to get him to fess up. Perry and Kudrow are remarkable to watch in this scene, bouncing off each other effortlessly and edging each other closer to the big reveal. When Chandler finally gives in and confesses to being in love with Monica, we’re left with another of the show’s most iconic moments and one that proves Perry’s ability to balance hilarity with heart. 

8. “The One With the Proposal Part 2” (Season 6, Episode 25) 

Who didn’t cry while watching this episode? “The One With the Proposal” is a two-part event that follows Chandler as he tries to propose to Monica despite the many obstacles that come his way. After a chance encounter with Monica’s ex Richard (Tom Selleck), a slipup from Joey, and more missteps stranger than fiction, Chandler finally arrives at Monica's apartment to find that she’s decorated the house with candles and is kneeling to propose. As Monica begins to cry, Chandler takes the lead and proposes while giving a tear-jerking monologue that proves Perry’s range as an actor. While this episode might not be Chandler’s funniest, it’s one of his best for offering a new side to his otherwise steadfast sarcasm, and showing just how much heart he actually has. 

9. “The One With All the Cheesecakes” (Season 7, Episode 11) 

It’s rare to see Chandler and Rachel paired up on Friends, but when we do, it makes for some of the show’s most hilarious moments. In this Season 7 episode, Chandler and Rachel sneak a bite of a cheesecake meant for their neighbor, and all hell breaks loose. The duo basically fall in love with the dessert, even going so far as to eat it off the floor, and their gluttonous fixation paves for some of the most palpable chemistry between Perry and Aniston onscreen. Fighting over cheesecake is a simple premise, and yet the duo bring in such comedic gravitas that you’ll find yourself begging for a bite yourself. The episode also ends with one of Friends’ most iconic Joey moments, and it’s honestly just a hilarious watch all around. 

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

One of Chandler’s many memed moments off Friends, this Season 8 episode sees our titular tough guy falling in love with the simple act of taking a nice bath. After confessing to Monica that he only likes taking baths with her, Monica’s adamant on proving the merits of a self-care bath to her husband, setting up a soaky evening with salts, candles, petals, and the whole works. Eventually, Chandler can’t get enough of this simple luxury, even going so far as to steal one of Monica’s bath nights she set up for herself. This episode proves Perry’s ability to turn a simple premise into his own yet again, and is one of the many reasons why we all love Chandler Bing.

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