7 ‘Friends’ Episodes That Highlight Why Matthew Perry’s Chandler Bing Was So Beloved

It was hard not to fall in love with Matthew Perry‘s Chandler on Friends. Chandler was our relatable king, our favorite lovable loser, and as Decider’s Brett White wrote, our light of hope for friendless weirdos.

In the original pilot script for the series, Friends co-creators David Crane and Marta Kauffman described Chandler Bing as “droll,” “dry,” and “a wry observer of everyone’s life.” But in Perry’s hands, Chandler became so much more than the sarcastic comments he had to offer. Under Perry’s guidance, Chandler was sweet, Chandler was romantic, and Chandler was vulnerable.

In fact, though David Schwimmer and Jennifer Aniston were clearly meant to be the show’s romantic leads—the never-ending saga of Ross-and-Rachel—the natural chemistry between Perry and Courtney Cox led to the unexpected romance between Chandler and Monica. That relationship breathed new life into the show, and propelled it for five more seasons. And most fans these days agree: Chandler and Monica are way better Ross and Rachel.

It’s no wonder Chandler was a fan-favorite, and why the unexpected and tragic death of Matthew Perry—who was found dead in his hot tub at the age of 54 on Saturday evening—has hit Friends fans so hard. And it’s no wonder so many are turning to their favorite Chandler episodes of Friends for comfort. With over 10 seasons and more than 200 episodes of Friends—all streaming on Max—there are plenty of stand-out moments for Miss Chanandler Bong to choose from, and your favorite may not be on the list. Keeping that in mind, here are just a few of our seven favorite Chandler episodes of Friends.

1. Season 1, Episode 7: “The One with the Blackout”

   Perry’s exaggerated, comedic facial expressions are the star in this early Friends episode, which finds Chandler trapped in an ATM vestibule with Victoria’s Secret model Jill Goodacre, during a New York City black out. Much of the episode features Chandler’s inner monologue via a self-deprecating voiceover from Perry, and damn if it isn’t always hilarious. I still reply “Gum would be perfection,” whenever someone offers me a stick.

   WATCH THE ONE WITH THE BLACKOUT ON MAX

3. Season 2, Episode 13: “The One After the Super Bowl: Part 2”

   Perry worked opposite yet another gorgeous guest star the very next season: Julia Roberts, who plays a former classmate of Chandler’s. Chandler thinks he has a shot with his smoking-hot former friend, but it turns out she was just looking to get revenge on him for humiliating her in the fourth grade. Cue the classic sitcom prank: The woman steals the man’s clothes. Perry flailing around naked in that bathroom stall remains one of the series’ most iconic scenes, and proof that his physical comedy was just as hilarious as his dry delivery.

   WATCH THE ONE WITH THE SUPER BOWL PART 2 ON MAX

4. Season 3, Episode 25: “The One at the Beach”

   Though it’s mostly a Ross-and-Rachel episode, the Season 3 finale also plays an important role in the saga of Monica and Chandler. Monica, bummed about being single, laughs in Chandler’s face when he offers to be her last-resort boyfriend. (“Am I not boyfriend material?” “You’re Chandler!”) Obviously, Chandler is offended. But eventually, the two make up, and the sizzling chemistry between Perry and Cox obviously didn’t go unnoticed by the producers. Even if it took them another full season to get there.

   WATCH THE ONE AT THE BEACH ON MAX

5. Season 4, Episode 3: “The One with the Cuffs”

   Perry once again proved himself to be the master of timing and facial expressions in the episode where he dates Rachel’s boss, and ends up hand-cuffed to the desk in her office. It’s a rare but welcome Chandler-and-Rachel episode. Perry and Aniston play off each other perfectly, with an easy back-and-forth. Perry’s look of incredulity after hitting his head with the file cabinet, seen above, remains one of my favorite jokes of the series.

   WATCH THE ONE WITH THE CUFFS ON MAX

6. Season 5, Episode 1: “The One After Ross Says Rachel”

   Any Monica-and-Chandler lover knows that Season 5 of Friends is the season. It’s the season of the sexy secret! It all starts with this season premiere which finds these two new lovebirds desperate for a moment of privacy during their last few hours in London—because London is the only place they are “allowed” to hook up. But after it becomes clear how badly they both want, they decide to keep the good sex going—eventually blossoming into arguably one of the greatest romances in sitcom history. The chemistry between Perry and Cox just can’t be beat.

   WATCH THE ONE AFTER ROSS SAYS RACHEL ON MAX

7. Season 5, Episode 8: “The One with the Thanksgiving Flashbacks”

   You gotta love the Friends episodes that mock ’80s fashion, and Chandler’s “flock of seagulls” hairdo in this Thanksgiving flashbacks episode might just take the cake. But it’s also such a treat for Chandler fans to see some backstory for his character—including a rude comment he once made about Monica. Don’t worry, he apologizes, and we even get the sweet moment when Chandler tells Monica he loves her for the very first time.

   WATCH THE ONE WITH THE THANKSGIVING FLASHBACKS ON MAX

8. Season 6, Episode 25: “The One with the Proposal: Part 2”

   Every once in a while, the Friends got to display their dramatic chops as actors. Nowhere did Perry do that better than in the heartfelt, tear-jerker Season 6 finale, where Monica proposes to Chandler. Both Perry and Cox will break your heart with their genuine tears, as Chandler stammers out why he wants to spend the rest of his life with Monica. Only cold-hearted robots won’t cry watching it.

   WATCH THE ONE WITH THE PROPOSAL PART 2 ON MAX