Matthew Perry’s 5 Funniest Moments on ‘Friends’

Following the death of actor Matthew Perry at age 54, fans are looking back on his body of work and remembering his most iconic role, that of Chandler Bing on the beloved sitcom Friends. For 10 seasons, Perry's performance as the snarky-but-sweet member of the group led to some of the show's biggest laughs and most quotable moments.

We all know classics like "Could I be more sorry?" and "My scone! My scone!" In memory of Matthew Perry and his comedic legacy, here are five other iconic moments from Chandler Muriel Bing.

Chandler meets Jill Goodacre

"The One With the Blackout" from Season 1 saw Chandler locked in an ATM vestibule (or is it an atrium?) during a power outage. Luckily for him, supermodel Jill Goodacre is also stuck in there, and Chandler slowly spirals while trying to overcome his nerves and ask her out. The entire thing plays out almost completely via his inner monologue, giving the audience a glimpse into the insecurity and neuroses that would come to define the character.

Chandler wears panties

In Season 2's two-parter "The One After the Super Bowl," the gang hang out on a film set with the show's biggest celebrity guest stars yet. This rogue's gallery of '90s legends included Jean Claude Van Damme, Brooke Shields, Chris Isaak, and most notably, Julia Roberts, who played Susie Moss, an old classmate of Chandler's. Susie resented Chandler so much for teasing her during their time at high school that she enacted her revenge by seducing him, persuading him to put on a pair of women's underwear, and then absconding with his clothes. The plot culminates in this great moment where Chandler, stranded in a bathroom stall, calls on Ross and Joey for help.

Chandler goes to Yemen

Janice, Janice, Janice. In a bid to finally get rid of his annoying ex-girlfriend, Chandler did the honest, honorable thing. Just kidding. He lied his ass off and told her he was moving to Yemen. This extended sequence at the airport, in which he realizes he can't simply pretend, and has to actually go through with his ruse—buying a $2,000 ticket and boarding the plane—is an exquisite exercise in cringe.

Chandler kisses everybody

Chandler and Monica keeping their relationship a secret led to some of the sitcom's best farcical moments, including this scene where they each forget for just a second that they're not alone. After kissing Monica goodbye, you can see the moment in Chandler's eyes where he realizes what he's done, and has to style it out by kissing a shocked Rachel and Phoebe with equal gusto.

Chandler and Monica get engaged

One of Chandler's finest moments in the show is also one of the least funny. This incredibly earnest scene, in which Chandler and Monica propose to each other, eschews all of the character's trademark sarcasm and bite in order to lay bare the beating heart of the show's most integral romantic relationship (no offense to Ross and Rachel).

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