IN THE SPOTLIGHT: Matthew Perry’s most memorable episodes in ‘Friends’

IN THE SPOTLIGHT: Matthew Perry’s most memorable episodes in ‘Friends’

/ 01:57 PM October 30, 2023

Matthew Perry. Image: Twitter/@FriendsTV

Matthew Perry. Image: Twitter/@FriendsTV

Matthew Perry’s remarkable role as Chandler Bing — who makes jokes when he’s uncomfortable — in the hit sitcom “Friends” was seared into the hearts of many, as his sardonic character turned out to be a mask for his inner demons. Apart from his puns and comedy, he was someone who just wanted to be truly happy.

Surrounded by the company of his co-stars Jennifer Aniston, Courteney Cox, David Schwimmer, Matt LeBlanc and Lisa Kudrow, Perry’s Chandler was a beloved fixture in pop culture as his beloved character represented millions of adults navigating awkward chapters in their lives. His knack for sarcastic remarks and physical comedy is relatable to many 20-somethings on a constant search for their purpose, choosing to express their pain in derision to show that “everything is fine.”


Sure, Perry had other roles — Joe Quincy (“The West Wing,” for which he was nominated for two TV acting awards); Nicholas ‘Oz’ Oseransky (“The Whole Nine Yards,” with Bruce Willis); Oscar Madison (“The Odd Couple,” with Thomas Lennon); Ted Kennedy (in the series “The Kennedys – After Camelot”); and, Ron Clark (“The Ron Clark Story,” for which he bagged an Emmy nomination). Still, the role that endeared him the most to his fans was as Chandler.


But beyond his beloved role, Perry wanted to be known as someone who’s determined to help others struggling with mental health and addiction. He certainly knew what he was talking about. As what he stated in the introduction of his memoir, “Friends, Lovers, and the Big Terrible Thing,” “My name is Matthew, although you may know me by another name. My friends call me Matty. And I should be dead.”

Looking back at his most memorable episodes is a tall order since it means rewatching 10 years worth of material, but allow us to recall Perry’s memorable moments in “Friends.”

The One with the Proposal (season 6, episodes 24 and 25)

Arguably one of the most unforgettable season finales in the show’s history, Chandler was desperate to ask Monica to marry him, and while it ended up with her getting down on one knee, the former finished their proposal in a tearful fashion.

“I thought that it mattered what I said or where I said it. Then, I realized, the only thing that matters is you. You make me happier than I ever thought I could be. And if you let me, I will spend the rest of my life trying to make you feel the same way,” he said, which Monica happily accepted with a kiss.

The two-part episode also showed Chandler’s vulnerability after he confronted Monica’s ex-boyfriend Richard saying, “This is unfair. You had your chance with her and you blew it. And this is my chance and I’m not going to blow it because we are meant for each other.” Many sitcoms are often confused with comedy and confrontation when a love triangle happens, but Chandler’s monologue showed that it’s possible to be angry that they couldn’t give a significant other the love that they deserve, and not because they’re simply a romantic rival.

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

While Ross was desperately trying to confess to Rachel, Chandler finds himself stuck in an ATM vestibule with Victoria’s Secret model Jill Goodacre during a sudden blackout. His inner monologue about being in the same room with a celebrity was painstakingly relatable in the best way possible as he didn’t want to make out of himself — even if he ended up choking himself while chewing gum.

The One where Chandler Can’t Cry (season 6, episode 14)

Chandler admitted that he’s not much of a crier and is “dead inside,” despite his friends’ efforts to make him shed a tear. Monica’s efforts to elicit some emotion, where she talked about them getting married, having children, and their eventual death, turned out to be worthless. The episode is a funny one, but it was also a comforting reminder that not everyone gets in touch with their emotions, and it’s okay.

The One with all the Thanksgivings (season 5, episode 8)

The first half of the episode showed Monica upsetting Chandler after revealing to him the truth of how he lost his toe years ago. But the initial dismay turned out to be one of the most romantic moments in the show, after he breaks out of his sarcastic mold when the love of his life shimmied with a raw turkey in yellow sunglasses.

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After blurting out “you look so great. I love you,” he transformed into a bumbling fool which was happily accepted by Monica. The moment turned out to be one of the sweetest in “Friends’” history, as it showed the silliness and romance of MonDler in its truest form.

The One with all the Cheesecakes (season 7, episode 11)

Chandler and Rachel are probably one of the most underrated duos in “Friends,” but when they spend time together, they find themselves in the quirkiest of antics — including their unhealthy obsession with a cheesecake from Mama’s Little Bakery in Chicago, Illinois. The mistakenly-delivered package turned out to be the best cheesecake they ever tasted, almost to the point of them not minding eating if off the floor.

The One where Chandler Can’t Remember which Sister (season 3, episode 11)

After downing shots of vodka to move on from Janice, Chandler ends up spending the night with one of Joey’s sisters — but he ends up not remembering which sister he hooked up with. He ended up pretending to be interested in pursuing a relationship with the sister, even though he only wanted to have fun.

The One with the Birth Mother (season 10, episode 9)

The “low motility” of Chandler’s sperm and Monica’s “inhospitable environment” proved they are unlikely to conceive a child, leading them to act as a doctor and reverend in order to adopt a baby from a prospective birth mother named Erica. After their act was discovered, this led to Chandler convincing Erica to “consider” them as parents because his wife is an “incredible woman” who is “always right.”

“I love my wife more than anything in this world. And it kills that I can’t give her a baby. I really want a kid. And when that day comes, I’ll learn how to be a good dad,” he told Erica, while noting how much Monica always wanted to be a mother for so long.

The One with Chandler’s Dad (season 7, episode 22)

Monica convinces Chandler to reconcile with his estranged father, a drag performer named Helena Handbasket, in Las Vegas. While their reconciliation is a far cry from the usual dramatic parent-and-child reunions on TV, the moment of emotion between them is a heart-wrenching one, as it proves there’s hope for people who are not — or will never be — in speaking terms with their parents. That even if Chandler and Helena will not have the closest relationship, them being on speaking terms is more than enough.

TAGS: Friends, Matthew Perry

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