Unforgettable Moments: Matthew Perry's Top 10 Episodes of 'Friends'

Matthew Perry, the renowned actor, sadly passed away at the age of 54 over the weekend. With a comedy career that spanned from his teenage years until his untimely death, Perry's most cherished and embraced role was that of the bumbling, sarcastic, yet endearing character, Chandler Bing, in the hit TV show, Friends.

Alongside his talented co-stars Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, and David Schwimmer, Perry played a crucial role in elevating Friends from a conventional sitcom to a cultural phenomenon that resonated with audiences across generations. The show not only captivated viewers week after week but continues to do so through reruns and streaming platforms. Perry's contributions throughout the 10-season run of Friends resulted in numerous iconic moments, making it a challenging task to select his best episodes. Although we may unintentionally omit some personal favorites, the following episodes showcase the brilliance of Chandler Bing and Matthew Perry, season by season.

Six friends - Ross Geller, Rachel Green, Monica Geller, Joey Tribbiani, Chandler Bing, and Phoebe Buffay - reside in vibrant New York City, navigating through a decade of life's trials and triumphs. Across ten eventful years and seasons, this tight-knit group experiences valuable life lessons, cherished bonds, romantic entanglements, intense drama, unwavering friendship, and uproarious comedy.

Cast Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, Matthew Perry, David SchwimmerMain Genre SitcomGenres Romance, SitcomRating TV-14Seasons 10Studio NBC

1. "The One With the Blackout"

Season 1

2. "The One Where Heckles Dies"

From the moment the first episode aired, Chandler Bing captured our hearts with his impeccable comedic timing and physical expressions. Whether it was the live studio audience or those of us at home, we spent every Thursday night laughing along with our favorite Friends. However, some of Chandler's funniest moments occurred during the blackout episode, where he found himself stuck in an ATM vestibule with supermodel Jill Goodacre. What truly made these moments hilarious were the inner thoughts that Chandler shared through voiceover. A perfect example is when he initially rejects a piece of gum from Jill, only to reconsider and admit, "On second thought, gum would be perfection." But deep down, he criticizes himself, thinking, "Gum would be perfection? I loathe myself." Trying to maintain his cool demeanor, Chandler casually blows a bubble, only to accidentally spit out the gum. After retrieving it and putting it back in his mouth, he suddenly realizes it's not even his gum. Panic sets in as he starts to choke! The delivery of these lines by Chandler's voice is nothing short of pure genius, leaving us in stitches of laughter.

Season 2

3. "The One Where Chandler Can't Remember Which Sister"

In this episode of Season 2, Chandler reveals his more vulnerable side as the cranky Mr. Heckles unexpectedly passes away, leaving Monica and Rachel with all of his belongings. As the group cleans up Mr. Heckles' apartment, Chandler surprisingly discovers the commonalities he shares with him - both were voted Class Clown and turned down attractive partners due to minor flaws. For instance, Chandler had rejected women because of their large nostrils, similar to Mr. Heckles' aversion to big gums. Throughout the episode, Chandler transitions from fear of ending up alone to recognizing that he doesn't have to precisely emulate Heckles' path in life. He realizes he can forge his own way. In fact, despite her large head, he decides to finally pursue a woman from his office whom he had previously avoided asking out. The post-credits scene is uproarious as Chandler muses to himself about his head appearing like a golf ball next to hers. This is classic Chandler.

Season 3

Still somewhat shocked by the news of his ex, Janice, being married with a child on the way, Chandler seeks solace in consuming Jell-o shots during Joey's birthday party. In a hazy state, he ends up engaging in a flirtatious encounter with one of Joey's sisters, leaving him perplexed about which sister it was. Seeking assistance from Ross, Chandler decides to visit the Tribbiani residence and inquire about Mary Angela, the sister he had the encounter with, in hopes of identifying her. However, his plans take an unexpected turn when he realizes that all of Joey's sisters are present for a family dinner. Chandler's witty dialogue during this encounter inevitably leads to him receiving a well-deserved punch to the face from the most formidable of Joey's sisters, Cookie.

4. "The One With the Embryos"

Season 4

5. "The One Where Everybody Finds Out"

Season 5

Another memorable quote from the show Friends was created in this particular episode: "They don't know that we know that they know we know." As Phoebe catches Monica and Chandler in the act, it triggers a series of amusingly awkward interactions between Phoebe and Chandler. Both Kudrow and Perry deliver exceptional performances in this episode. Perry, in particular, shines as he playfully invites Phoebe to touch his bicep and potentially more. His humorous lines, such as "It's very nice," referring to Phoebe's bra, and "I'm very excited we're going to have all the sex," make this episode one of Chandler's finest moments. Additionally, this episode features a heartwarming scene where Chandler confesses his love for Monica.

6. "The One Where Chandler Can't Cry"

Season 6

7. "The One With the Engagement Picture"

The season finale with Monica is always a delight, but this one showcases Perry's comedic genius and spot-on timing. Monica's quest to make him cry unveils some of his funniest moments. One memorable line from this episode is when he says, "Well, that surely warms up my cold tin chest." At last, tears stream down his face after witnessing the constant struggles between Ross and Rachel, who everyone knows are destined to be together. Once the floodgates open, even the smallest things trigger his outbursts of weeping.

Season 7

Monica, realizing that she and Chandler should have their engagement photo featured in the newspaper, comes to the realization that Chandler does not possess photogenic qualities — to put it delicately. Despite his genuine smiles and laughter, as soon as the camera clicks, his expression hilariously transforms into a grimace. Throughout Friends' 10-year run, Perry's portrayal of Chandler's awkward smiles serves as some of the best physical comedy. Regardless of how often it occurs during this episode, it is simply impossible not to burst into laughter upon seeing his peculiar "smile" in the photos.

8. "The One With the Halloween Party"

Season 8

Monica throws a Halloween party and surprises Chandler with a pink bunny costume. The sight of him dressed as a big fluffy pink bunny is absolutely hilarious. Meanwhile, Monica stuns everyone as Catwoman, but that's no surprise – she always looks amazing in any costume. She admits to Chandler that she couldn't find anything other than the pink bunny outfit. "It was either the pink bunny or nothing," she explains. In his usual deadpan voice, Chandler responds, "Always better to choose nothing!" Ross arrives at the party dressed as "Spudnik," a combination of a potato and a satellite, prompting Chandler to crack his classic jokes about Ross looking like a doody and later teasing that Ross appears "a little flushed." The epic arm-wrestling match between Ross and Chandler ensues, and Chandler's constant attempts to impress Monica are truly heartwarming.

9. "The One With Ross's Inappropriate Song"

Season 9

While this episode, titled

10. "The One Where Estelle Dies"

, showcases Ross's ability to make Baby Emma laugh for the first time by rapping "Baby Got Back," it also delves into Chandler's recurring insecurities about Monica's past relationship with Richard (Tom Selleck). Upon discovering that Richard's apartment is up for sale, Chandler and Joey arrange a viewing with a real estate agent, during which Chandler unleashes a barrage of insults, mostly targeting Richard's mustache. However, his curiosity gets the better of him when he stumbles upon a video on the shelf labeled with Monica's name. Reluctantly, Chandler gives in to his desire to watch it. The moment is heartwarming as it confirms that Monica has moved on from Richard and is wholeheartedly committed to her relationship with Chandler.

10. "The One Where Estelle Dies"

Season 10

The last season brought many changes for our beloved six New York City friends. In this episode, Monica and Chandler make the decision to leave the bustling city and settle into a peaceful suburban life. Excitement fills the air as they discover their dream house, only to be surprised by another potential buyer. To their astonishment, it turns out to be none other than Janice. While Season 9 marked Monica's final release from Richard, this episode provides Chandler with an opportunity for closure with Janice as well. With unforgettable moments and a heartfelt farewell to Janice and the city, this episode encapsulates the essence of Friends. Don't miss out on streaming Friends on Max in the U.S.

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Editor's P/S

Matthew Perry's portrayal of Chandler Bing in the iconic TV show "Friends" was truly remarkable. His comedic timing, witty one-liners, and hilarious facial expressions made Chandler a fan-favorite character. Among the many memorable episodes featuring Chandler, a few stand out as prime examples of his comedic brilliance.

One such episode is "The One with the Blackout" from Season 1. In this episode, Chandler finds himself trapped in an ATM vestibule with supermodel Jill Goodacre during a city-wide blackout. The ensuing chaos and Chandler's inner monologue provide some of the funniest moments in the entire series. From his desperate attempts to impress Jill with his knowledge of gum to his ill-fated encounter with a piece of gum, Chandler's misadventures in the ATM vestibule are nothing short of hilarious.

Another standout episode is "The One with Mr. Heckles" from Season 2. In this episode, Chandler discovers that he has more in common with the recently deceased Mr. Heckles than he would like to admit. As Chandler grapples with the fear of ending up alone like Mr. Heckles, he embarks on a journey of self-discovery and ultimately decides to pursue a woman he had previously avoided due to her large head. The episode ends with a hilarious post-credits scene where Chandler imagines what it would be like to have a head the size of a golf ball next to his girlfriend's large head.