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Could we BE any more excited to dive into the world of Chandler Bing’s ten greatest hits? Prepare for sarcasm, awkwardness, and a dash of Chandler’s signature wit. From the Yemen ruse in season 4 to the iconic “The One with the Proposal” double whammy in season 6, we’ve got the cream of the Chandler crop.

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10 “The One After the Superbowl Pt. 2”

Our first deep dive into Chanlder’s best moments starts with one of Friends’ most viewed episodes. A staggering 52.9 million people tuned in to watch following Superbowl XXX. Episode 13 of season 2 follows Chandler bumping into an old friend and subsequently going on a date with the friend. Who is the friend? Well, it’s none other than Julia Roberts. Roberts plays Chanlder’s old school yard friend Susie Moss.

Susie reminds Chandler of an event from their fourth-grade school play. Chandler lifted her skirt during the play, leading to her unfortunate nickname, “Susie Underpants.” Despite the childhood mishap, the two decide to go on a date.

The humor kicks up a notch when Susie suggests that Chandler wear her panties on their date, a proposal that he accepts with a mix of confusion and intrigue. The date takes a turn for the wild when Susie lures Chandler into the restaurant’s bathroom under the pretense of intimacy. Instead, Susie leaves him stranded in a bathroom stall, wearing nothing but her panties.

As Susie leaves the bathroom with Chanlder’s clothes, he replies, “I hope you realize you’re not getting these underpants back!” This is her revenge for the fourth-grade incident, leaving Chandler to navigate his way out of the jam in a hilariously awkward fashion.

9 “The One Where Ross and Rachel… You Know”

In season 2, episode 15, we witness Chandler Bing’s commitment to relaxation. While spending his Days of Our Lives paycheck, Joey splurges on two armchairs and a big-screen TV. The result? A hilarious yet relatable saga of two buddies who vow never to leave their newfound thrones.

Phoebe, the voice of reason, can’t help but mock their devotion to the chairs. “I can’t believe two cows made the ultimate sacrifice so you could watch TV with your feet up,” she quips. Chandler defends the decision with his signature wit, claiming they were “chair-shaped cows” unfit for the wild.

The banter continues as Joey raises a concern: What if they need to pee? Chandler’s solution? Cancel the sodas. The trio of Phoebe, Chandler, and Joey engage in a battle of perspectives, with Phoebe advocating for the “three-dimensional people” outside. But for Joey and Chandler, inside is good, and outside is bad.

Chandler dismisses a potential fire alarm as they resist attempts to break their lethargy. “It’s not warm yet. We still have time,” he declares. “The One Where Ross and Rachel… You Know” stands out as a testament to Chandler Bing’s hilarious and unforgettable moments in the Friends series.

8 “The One Where Chandler Can’t Remember Which Sister”

Chandler’s escapades at Joey’s birthday party take a hilarious turn in season 3, episode 11. After drowning his sorrows in Jello shots following Janice’s return to her ex, Chandler finds himself in a chaotic situation. Drunk and philosophical, he contemplates speed dialing while complimenting one of Joey’s seven sisters on her “huge breasts.”

The next morning, Chandler faces the consequences of his drunken actions. Unable to recall which sister he got intimate with, he delivers classic Chandler one-liners and laments the group’s “woo-hooing.” The following confusion among the friends as to which sister Chandler could have been with adds to the comedic chaos. Monica then scolds Chandler for risking Joey’s wrath.

The episode reaches its peak when Chandler apologizes to Joey’s sister, Mary Angela. But, whoops, it’s not Mary Angela he is apologizing to. Chandler’s mix-ups lead to comedic misunderstandings and his signature self-deprecating humor. Friends fans remember this episode as an outstanding showcase of Chandler’s wit and the sitcom’s ability to turn awkward situations into comedic gold.

7 “The One with the Hypnosis Tape”

Rachel, fed up with Chandler’s smoking habit, introduces him to a hypnosis tape that promises to break the cigarette spell. Chandler, always the witty skeptic, tries everything to kick the habit, including sticking the tape on like a stop-smoking patch, which promptly falls off.

Hilarity ensues as Chandler listens to the hypnosis tape in his sleep. The soothing voice encourages him to embrace a new identity—that of a “strong, confident woman who does not need to smoke.” The result? Chandler struts around like a diva, borrowing Monica’s Chapstick with newfound grace and confidence. His towel-clad entrance into the living room baffles Joey, but the laughter doesn’t stop there.

Joey, the ever-entertaining sidekick, decides to have some fun with Chandler’s hypnotic vulnerability. He records a message on the tape to get Chandler to make Joey cheese sandwiches and buy him expensive pants. Chandler bolts upright in bed and stares at his tape player.

In season 3, episode 18, Chandler’s attempt to quit smoking becomes a sidesplitting saga of self-discovery and unexpected consequences. The episode showcases Matthew Perry’s comedic timing and enduring charm.

6 “The One with the ‘Cuffs”

Season 4, episode 3 takes an unexpected turn when Chandler ends up half-naked and handcuffed to a chair in Rachel’s boss’s office. As Joanna, Rachel’s boss, rushes off on an unexpected meeting, Chandler is handcuffed as part of a saucy gag.

The ensuing comedy involves Chandler answering the phone with his nose and flipping through a lingerie catalog with his teeth. The situation escalates when Rachel, armed with a key to Joanna’s office, discovers Chandler in his half-naked glory.

Soon, Chandler is begging to be let out of the handcuffs. At one point, Rachel shouts, “…you got yourself into those cuffs, you get yourself out of them.” Chandler quips, “I can’t get myself right out of them. You must have me confused with the Amazing Chandler.”

The episode showcases Chandler’s ability to turn awkward situations into laugh-out-loud moments. With memorable lines and physical comedy, this Chandler-centric episode is one of the most hilarious moments in Friends’ history.

Bonus Fact: When Chandler is handcuffed to a filing cabinet after Rachel uncuffed, then re-cuffed him, the filing cabinet opens, hitting Chandler in the back of the head. The drawer was not supposed to open. Matthew Perry’s and Jennifer Aniston’s reactions were real.

5 “The One with the Dirty Girl”

Chandler shows his softer side as he navigates the tricky waters of gift-giving in season 4, episode 6. Faced with the challenge of buying a birthday present for Joey’s girlfriend, Kathy, Chandler goes above and beyond. Purchasing an early edition of Kathy’s favorite book, The Velveteen Rabbit, Chandler’s effort is both thoughtful and hilariously excessive.

The episode unfolds with Chandler nonchalantly describing his quest to find the book, involving bookstore visits, talks with dealers, and even calls to the author’s grandchildren. His deadpan humor shines as he insists on the rarity of the gift while warning against touching it due to “destructive oils.” Meanwhile, Rachel and Phoebe point out the underlying message: “I secretly love you, roommate’s girlfriend!”

Chandler then learns that Joey purchased Kathy a humble gift, a pen that doubles as a clock. Chandler is torn between keeping the grand gesture or letting Joey take credit. Chandler’s awkward attempts to downplay his feelings add charm to the episode.

Ultimately, Chandler sacrifices his gift for Joey’s relationship. The episode culminates in a memorable moment when Kathy expresses gratitude to Chandler, not Joey. Chandler’s tongue-tied “Uhl… ell” response captures the essence of his bumbling yet endearing character.

4 “The One with All the Rugby”

In season 4, episode 15, Chandler faces the ultimate challenge – breaking free from his ex-girlfriend Janice. As Chandler gets his nails done with Rachel, Janice, now divorced and ever-persistent, makes a surprise appearance at the salon. In his classic dry humor, Chandler declares, “I can’t stand the woman,” leading to a wacky plan to escape her clutches.

The dialogue between Chandler and Janice unfolds as Janice lists potential relocation cities, only to be met with Chandler’s deadpan response of Yemen. The elaborate scheme continues with Chandler packing up his belongings and attempting to “purchase” a pretend ticket to Yemen at the airport.

The episode climaxes as Chandler, faced with Janice’s ongoing chase, boards the plane to Yemen. Janice lovingly declares her commitment to writing him every day at “15 Yemen Road, Yemen.” Chandler’s deadpan humor and Janice’s unwavering persistence make this episode stand out in the Friends series. It showcases Chandler Bing at his finest—clever, sarcastic, and always trying to escape the clutches of his ex-love.

3 “The One with the Proposal Pt. 2”

In the saga of Chandler Bing’s memorable moments, one shines above the rest—the proposal debacle in season 6’s two-part final. Chandler takes center stage as he continues to badmouth marriage to throw Monica off his proposal plans. However, he is unaware that Richard, Monica’s ex, has plans to win her back.

While on a date with Monica, Chandler delivers a monologue on the unnaturalness of marriage, citing pigs’ promiscuity as evidence. Monica questions his sincerity, leading to a dramatic confrontation. The mess escalates when Joey reveals Richard’s unexpected marriage proposal to Monica. Ending his ruse, Chandler proclaims, “I’m gonna get the ring! I’m gonna get the ring! I’m just going to propose!”

Chandler rushes to confront Richard in his apartment. However, in an unexpected turn, Richard becomes an unlikely ally, urging Chandler to go after Monica. Ending with “don’t let her go.”

The emotional rollercoaster culminates in a heartwarming proposal, complete with Chandler’s signature humor and Monica’s tearful acceptance. The engagement brings a triumphant end to the episode, sealing Chandler’s fate as the lovable, if not slightly neurotic, romantic hero of Friends.

2 “The One Where Chandler Takes a Bath”

Season 8, episode 13 brought us one of the top Chandler Bing moments. Monica, in her infinite wisdom, introduces Chandler to the concept of a relaxing bath. Chandler, being his usual sarcastic self, questions if Monica is high.

The banter between the two is classic Chandler, dismissing the idea of baths until Monica draws him one complete with candles, bubbles, and a plastic Navy ship. The result? Chandler, in the tub, realizing the flower smell isn’t so bad, accompanied by the line: “I’m going to need a bigger boat.”

As the scene progresses, we witness Chandler’s journey from a bath skeptic to a guy obsessed with getting into the tub. The bathtub becomes a hub for confessions and surprises, including Joey’s crush revelation and the announcement of Rachel and Ross’s baby’s gender.

This episode is a shining example of Chandler’s comedic brilliance, turning everyday activities into hilarious adventures. It’s a tribute to Matthew Perry’s flawless timing and delivery that made Chandler Bing an unforgettable character. So here’s to Chandler, the unexpected bath enthusiast, and the joy he brought into our lives.

1 “The One with the Mugging”

Chandler Bing’s foray into the advertising world in season 9, episode 15, is a rollercoaster of awkward hilarity. As he excitedly announces his new gig at Central Perk, Chandler’s news is met with cheers. Still, the bombshell drops when he reveals it’s an unpaid internship. Classic Chandler.

Decked out in a tie and briefcase, Chandler, the “intern,” faces the skepticism of his much younger colleagues. The comedic genius unfolds as Chandler struggles with the lingo—”kicks,” “skids,” and heaven forbid, “slorps.” His first assignment is to create a pitch for prototype sneakers with wheels. Joey, ever the enthusiast, offers $500, proving once again that Chandler’s misadventures are pure gold.

The sitcom genius hits its peak during a presentation where Chandler, with a bruised body, pitches an ad targeting kids. The punchline? “Not suitable for adults.” The irony of Chandler’s struggle to fit in and stand out is pure comedic gold, making it one of the most memorable moments in Friends history. Could Chandler BE any funnier?

+ “The One with the Embryos”

In this season 4 episode, an unexpected wake-up call forces Monica and Rachel to confront Chandler and Joey about the “cock-a-doodle-do-ing” going on in their apartment. Obviously, the female chick they bought is now turning into a rooster, according to the vet. They are just waiting for a second opinion.

Later, Phoebe leaves as she is preparing for the implantation of her brother’s and his wife’s embryos. The rest of the gang then deviates into a who knows who best moment after Joey says Monica is only upset because, since it’s her laundry day, she’s wearing her “old lady underpants.” With his typical wit, Chandler pipes in with, “I can check that for you.”

With a $10 bet on the line, Chandler and Joey guess the five remaining items in Rachel’s grocery bag. When they do, the stakes climb to $100, and they turn to Ross to create the questions. With the teams set, we learn any number of interesting facts and tidbits about Chandler, including the name of his father’s all-male Las Vegas burlesque show, his pet peeve, and the name on his TV Guide subscription.

With a tie game, they move to the lightning wound, but not before the stakes climb even higher. Chandler and Joey will give up the animals if they lose, but Monica and Rachel will have to give up their apartment. This “Apartment Switch Quiz” gives us plenty of laughs and reminds us of what Matthew Perry brought to the role of Chandler Bing.

You will be missed, Matthew!

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