Top 10 Matthew Perry 'Chandler' moments on 'Friends'

Matthew Perry, who was found dead at the age of 54 last week, was best known for starring on the series, Friends, as Chandler Bing. Of all the characters, Chandler was always the hardest to pin down, which made him the most interesting of the bunch. He wasn’t exactly a nerd, like David Schwimmer’s Ross, nor an endearingly arrogant, working-class actor, like Matt LeBlanc’s Joey. Chandler started the series as a self-deprecating (and often self-loathing), commitment-phobe data analyst and ended up as a much happier advertising copywriter married to Monica (Courteney Cox) and the adoptive father of twins – a transformation that so many of those who grew up on the show could identify with. It was Chandler who delivered many of the show’s most beloved zingers, but the moments when he displayed genuine emotion and vulnerability were often the show’s most touching scenes. 

Perry had a career in other movies and television shows, and he was particularly good as a smarmy politician on The Good Wife and a Republican lawyer on The West Wing. But he struggled with drug addiction for decades, which likely kept him from having the post-Friends career he might otherwise have achieved. 

His acting as Chandler was a key part of the special sauce that made the series such a huge hit. Chandler’s preppy exterior, corporate job, and cynical sense of humor hid the scars of his chaotic childhood. Perry played this complex character so well, he made it look easy. But there’s a saying in Hollywood, that death is easy but comedy is hard, and comic acting as consistently fine as Perry’s is incredibly difficult to pull off. Perhaps Perry’s own turmoil helped make his performance as Chandler so compelling – and while it’s impossible to mention all his great moments, here are some of the episodes on Friends that showcase Perry at his finest.

Best Chandler moments on Friends

1. Season 1, episode 7 – “The One with the Blackout”: It was before we knew much about Chandler when a blackout hit New York and he had the weird but good luck to get, as he put it, “trapped in an ATM vestibule with Jill Goodacre.” Goodacre, a Victoria’s Secret model, played herself as Chandler’s insecurity paralyzed him and he couldn’t manage to do anything right with her. His scenes are narrated in voiceover, as he is nearly frozen, making himself look dumb and weird when all he wants is to seem cool. It features one of the funniest lines in the history of the series, when he turns down her offer of gum, then changes his mind, telling her, “Gum would be perfection.” His expression after she kissed him goodbye and he couldn’t tell her how much he’d like to see her again was priceless sad-sack comedy. 
2. Season 2, episode 13 – “The One After the Superbowl, Part 2”: The United States and the world had fallen in love with Friends by the second season and the show had a post-Superbowl episode, which fans celebrated in watch-parties. It featured a number of A-list guest stars, among them Julia Roberts, who happened to be the world’s biggest movie star, as well as Perry’s girlfriend. She played Chandler’s old classmate Susie Moss. Chandler hoped Susie wanted to start dating, but it turned out she only wanted to take revenge on him for a prank he had pulled on her years ago. What he thought would be a steamy tryst turned into a disaster when she got him to strip and left him in the bathroom of a restaurant dressed only in her underwear.  It was a hilarious comic setpiece and they both played it brilliantly. 
3. Season 3, episode 11 – “The One Where Chandler Can’t Remember Which Sister”: After Chandler has a few drinks too many, he hooks up with one of Joey’s sisters – only afterward, he can’t remember which one. There is a great scene where Chandler has dinner with the Tribbiani family and is secretly trying to figure out which sister he fooled around with. People think of the 1980s as the decade of big hair, but Joey’s sisters – in the 1990s – were no slouch in that department. The contrast between them and the preppy Chandler is priceless. 
4. Season 3, episode 25 – “The One at the Beach”: The Ross-and-Rachel story was the centerpiece of this episode, but this season finale marked the real beginning of the Monica-and-Chandler romance. Monica, feeling down about not having a boyfriend, laughs out loud when Chandler offers to date her. “Am I not boyfriend material?” he asks, to which she replies, “You’re Chandler!” Chandler is miffed, but she manages to apologize. There was undeniable chemistry between the two and fans took note, anxiously waiting to see if this was the beginning of a beautiful more-than-friendship. It was, although it took a while to get there. 
5. Season 4, episode 3 – “The One with the Cuffs”: Perry’s talent for physical comedy was front and center in this episode, in which he dates Rachel’s boss and finds himself handcuffed to her office desk. It could have been sitcom fluff, but he is simply so funny, you’ll never forget it. 
6. Season 4, episode 15 – “The One with all the Rugby”: Trying to break up with his nasal, annoying, yet endearing girlfriend, Janice, he made up a crazy story about being transferred to Yemen for work. Chandler went all in on the lie, even buying a ticket to Yemen and boarding the plane.
7. Season 5, episode 1 – “The One After Ross Says Rachel”: This episode marked the start of the season dedicated to Monica and Chandler’s secret romance, and Monica always brought out the best in Chandler, both comically and dramatically. In the season premiere, the lovers try to find some privacy in London and it’s sexy fun from start to finish. 
8. Season 5, episode 14 – “The One Where Everybody Finds Out”: Going all out to keep their romance a secret, Chandler and Monica construct an elaborate bluff where Chandler pretends to be into Phoebe and finally has to admit the truth. It’s a classic farce but with heart.
9. Season 6, episode 25 – “The One with the Proposal, Part 2”: This episode showed Chandler at his most vulnerable and endearing. While Chandler was known for his punchlines, his romantic dance with Monica to Eric Clapton’s “Wonderful Tonight” might bring a tear to your eyes. 
10. Season 7, episode 24 – “The One with Monica & Chandler’s Wedding, Part 2”: There was a lot going in the episode where Chandler and Monica finally got hitched, and fans everywhere were rooting for him not to mess things up. Of course, he kind of got cold feet, but eventually realized that they were meant to be together. This was one of the best-loved TV weddings of all time.