Matthew Perry's Five Essential Friends Episodes

Over ten seasons on Friends, Chandler Bing evolved from a hyper-insecure, sweater vest-wearing single guy to satisfied family man. But thanks to Matthew Perry's massively winning performance, the character never lost his self-effacing charm or wit. In honor of the Emmy-nominated actor's passing on October 28, here's a tribute to five of his finest showcases on the NBC smash (in order of airing).

"The One Where Rachel Finds Out" (Season one)

In the pivotal season finale of Friends' first season, Perry further cemented Chandler's snarky cadence and charm in a key scene where Chandler accidentally spills the beans to Rachel (Jennifer Aniston) that Ross (David Schwimmer) is in love with her. The setting is rather casual, with the friends sitting on a couch in Rachel and Monica's (Courtney Cox) apartment, when Rachel is surprised to open an elaborate gift from Ross only to have Chandler remind the gang of the last time Ross showed someone he loved them — by gifting her a crystal duck. Having realized what he said all too late, Chandler and Perry forever changed the dynamic of the series and our relationship with one of television's most popular characters. And he did all with two words: "Crystal duck."

"The One Where Heckles Dies" (Season two)

Perry shows off his vulnerable side after Monica and Rachel's downstairs neighbor, the cranky and eccentric Mr. Heckles, suddenly passes away. Rummaging through his apartment, Chandler is aghast to realize he and the old man shared too many similarities — right down to rejecting attractive women because of insignificant flaws. He soon decides to course-correct his life and ask out a coworker. Large head, be damned!

"The One With Chandler in a Box" (Season four)

Week to week, Perry seemed to give every episode the exact amount of whatever it needed to connect with audiences. Even when he was largely off-screen, as seen in this classic fourth season outing that finds Chandler at odds with his best friend, Joey (Matt LeBlanc), over a love interest, Kathy (Paget Brewster), at Thanksgiving. When Joey catches Chandler kissing Kathy and threatens to leave, Chandler is desperate to salvage both the holiday and his friendship. So, he does what only Chandler could do to make it up to Joey: locks himself in a box for six hours, in the middle of Monica's floor.

Perry's impeccable comedic timing steals the episode, even though his character spends most of the runtime out of sight.

"The One Where Everyone Finds Out" (Season five)

Chandler's narrative arc from human quip machine to becoming half of the series' beating heart hit a significant turning point in this all-timer episode, where the gang discovers (much to Chandler's chagrin) that he and Monica are dating. Moreover, than he and Monica are in love, and it all comes out with the help of a game of "sexual chicken" between Chandler and Phoebe (Lisa Kudrow) as the latter tortures the former by pretending to come on to him in an effort to get him to tell the truth about his relationship. The most hilarious display of sexual tension ensues, as Perry and Kudrow engage in a physical comedy showcase that is just as funny now as it was nearly twenty-five years ago.

"The One With the Engagement Picture" (Season seven)

"I don't know what it is, I just can't take a good picture," Chandler admits to Monica and Phoebe at the top of this episode. He proves his point to hilarious results when the couple pose for professional engagement photos. As soon as the camera starts to click, Chandler's natural smile morphs into an uncomfortable grimace. This is some of Perry's subtlest — yet most impressive — physical comedy work.

Friends is now streaming on Max.