The One With Matthew Perry's Most Iconic 'Friends' Moments

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Chandler Bing Best Moments — Photo:
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Over the weekend, the world lost a brilliant comedian in Matthew Perry. Perry had a résumé stacked with '90s and 2000s rom-coms (one of which was cult classic film 17 Again), successful TV series, and a critically acclaimed memoir titled Friends, Lovers, and the Big Terrible Thing, which candidly detailed his long-time battle with substance abuse. However, the actor was undoubtedly most well known for his portrayal of the beloved Chandler Bing on the long-running sitcom Friends.

Cast of Friends in the Living Room — NBC/Getty Images

The show was a ratings bonanza during its original run, ultimately shifting the television landscape with its witty dialogue, progressive (well, for the '90s, at least) storylines, and spot-on casting. But thanks to re-runs and DVD boxed sets and eventually streaming, the series became a comfort show for millions of Millennials — scratch that — for every generation. It was a comfort show for me. One that I — we — turned to for solace and, of course, laughter during hard times, breakups, periods of grief, bouts of loneliness, any time when you needed to feel like someone was there for you. No matter why or how or when you tuned in, each character became a friend. Chandler, with his self-deprecating humor and physical comedy, could put a smile on our faces when it hadn't been our day, our week, our month, or even our year.

More than 25 years since it premiered, the show continues to be regarded as one of the greatest sitcoms of all time. Although Perry has left Central Perk behind for good, his comedic genius couldn't BE more profound and his legacy will live on. With 10 seasons and more than 200 episodes, Perry told an innumerable amount of brilliant jokes and starred in a myriad of poignant storylines, but these are 10 of Chandler's most iconic Friends moments.

The One After the Super Bowl

Matthew Perry and Julia Roberts Hug and Smile On Set of 'Friends' — Getty Images

Julia Roberts guest starred in this episode that aired after the 1996 Super Bowl. The actress played Susie Moss, a woman from Chandler's past who, unbeknownst to him, asks him out in order to seek revenge for something he did in grade school. She gets it. Chandler is left wearing nothing but a pair of pink women's underwear in a public restroom. In real life, things went a bit better: After acting together in the episode, Roberts and Perry even dated for a bit.

The One With All the Thanksgivings

atthew Perry as Chandler Bing, Jennifer Aniston as Rachel Green, David Schwimmer as Ross Geller, Courteney Cox as Monica Geller Sitting on a Couch — NBC/Getty Images

Nobody does Thanksgiving like the crew on Friends, what with the amateur football games, run-away balloons, and Rachel's vile beef trifle. One character, however, is not so fond of the holiday, a result of many unfortunate memories associated with the day. Season's 5 Thanksgiving episode revisits the Turkey Days of Chandler's past, including one during which a young Monica accidentally cuts off his toe. The '80s flashback brings us Young Chandler's Flock of Seagulls haircut and lines like "righteous mac 'n' cheese."

The One Where Phoebe Hates PBS

When Chandler learns that Monica called him "the best she's ever had," he lets the news go to his head. He gets cocky, brags, and, in a move totally emblematic of the male psyche, breaks out his dorky Chandler dance on top of Monica's coffee table. Monica may have been rightfully annoyed, but fans everywhere are grateful.

The One With Chandler In a Box

Chandler Bing and Joey Tribbiani Hugging Outside of Chandler's Box — NBC/Getty Images

This is another brilliant Thanksgiving episode, but one in which we don't see much of Chandler. Chandler and Joey's girlfriend Kathy fall for each other and get caught kissing, leaving Joey hurt and betrayed. After begging for forgiveness, Joey decides Chandler should spend all day in a wooden box as his penance. Even from a box, Perry delivered comedy gems, like the way he pokes his finger through the air hole.

The One Where Nobody's Ready

Joey Tribbiani Doing Lunges in All of Chandler Bing's Clothes — NBC/Getty Images

This whole episode takes place during the span of 30 minutes of chaos leading up to Ross's big museum event that the whole gang is supposed to attend together. Instead of getting ready, Chandler and Joey begin fighting over a chair. Joey eventually gives up the chair, but takes the cushions with him, which leads to Chandler exclaiming, "The cushions are the essence of the chair!"

The One With All the Rugby

OH. MY. GOD. Chandler Bing and Janice (played by Maggie Wheeler) are one of the most iconic couplings in TV history, even though things didn't work out between the two during her long (and nasal) tenure the show. During one of Chandler and Janice's on-again stints, he tells her they can't be together because he's moving to Yemen. 15 Yemen Road, Yemen, to get specific.

The One With the Blackout

One of Chandler's best moments took place in the very first season. During a city-wide blackout, Chandler finds himself [this next part should be read through clenched teeth] trapped in an ATM vestibule with '90s supermodel Jill Goodacre (who made a cameo as herself). Chandler's inner-monologue narrates the scene, yielding some of his most unforgettable one-liners, including "gum would be perfection" and "I loathe myself."

The One With All the Kissing

After Chandler and Monica have their secret rendezvous in London (IN LONDON?!) at Ross' wedding, the two friends continue their fling in hiding. When Chandler accidentally kisses Monica in front of Rachel and Phoebe, he proceeds to smooch the other ladies to cover up their romance — a "European goodbye thing he picked up in London."

The One Where Everybody Finds Out

Chandler Bing and Pheobe Buffay In Doorway of Chandler and Joey's Apartment — NBC/Getty Images

This episode is pure television gold and eternally quotable. When Rachel and Phoebe find out that Monica and Chandler are secretly seeing each other, the two girls devise a plan to mess with the couple. That is, until those two find out about their scheme and create one of their own, which results in Chandler exclaiming, "Ah, yes! The messers become the messees." Things get more meta when Rachel and Phoebe find out that the couple knows they know. The whole facade comes to a head when Chandler and Phoebe go toe-to-toe in a seduction-off.

The One With the Proposal

Monica Geller and Chandler Bing Kneeling Holding Hands Engagement Episode — NBC/Getty Images

Chandler and Monica's engagement is my Roman empire, and also serves as a great reminder of what happens when you leave men in charge. Chandler attempts to throw Monica off the scent of his upcoming proposal, but takes it too far and ends up convincing her that they'll never get married. During the snafu, Monica turns to ex-boyfriend Richard for clarity, leaving fans wondering if this is the end for the iconic couple. Then comes one of the show's best surprises and most touching moments: After learning about Chandler's plan, Monica arranges her own candle-lit proposal, one that had the characters — and all of us — choked up.

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