Matthew Perry’s Top Moments Playing Chandler Bing on Friends

Chandler Bing’s on-and-off relationship with love interest Janice (Maggie Wheeler) was the ultimate reflection of his fear of commitment having grown up in a dysfunctional family. Yet, Janice had positive hopes for their relationship, with enough love to go around for both of them. In a last-ditch effort to break up with his annoying love interest, Chandler made up the story of his relocation to Yemen in the Season 4 episode titled The One With All the Rugby. Turns out he underestimated Janice’s clinginess, as not only did she accompany him to the airport with his luggage, but she also insisted on waiting until his flight took off. A defeated Chandler had to spend $2100 on actual flight tickets to Yemen and boarded the flight. Well, better a trip to “15 Yemen Road, Yemen,” than one more day with a clingy ex.

Scared as he was of commitment, Chandler Bing was never one to turn down a feel-good moment, especially after a post-heartbreak vodka. Viewers saw his post-heartbreak crisis play out severally in the 10-season run of the sitcom. However, the most hilarious was his hookup with one of Joey Tribbiani’s seven sisters at his (Joey) birthday party on The One Where Chandler Can’t Remember Which Sister. The next morning, he could not remember which sister he messed with in the storage room. Even after Joey hinted that it was Mary-Angela, Chandler still couldn’t put a face to the name. For all he knew, all seven could very well be clones of each other, in their red lipstick and puffy brunette curls. The family dinner scene where Grandma kept foiling his plans to identify her goes down as one of the most hilarious on Friends.

Friend’s season 6, episode 24 titled The One With the Proposal saw Matthew Perry’s character Chandler Bing shed his protective humor shield and tap into his romantic vulnerability. Divided into two half-hour slots, the first part captured Chandler’s plot to propose to Monica at a restaurant, which was ruined when Monica’s ex, Richard walked in and sat with them through the dinner date.
Scared Monica would discover the surprise before he got another chance to propose, Chandler took Joey’s advice and began acting nonchalant, making it clear he loathed the idea of marriage. His plans backfired, nearly driving Monica back into the arms of Richard. But just when he thought he’d lost his love after a city-wide search, Chandler found himself at the receiving end of the surprise proposal. Notably, the producers intended the emotional proposal to mark the sitcom’s finale given the ongoing studio drama at the time which was eventually resolved. Little wonder it had such memorable elements.

What would you do if you were trapped in an ATM vestibule with one of your favorite celebrities? In Chandler Bing’s case, he was completely star-struck in a role Mathew Perry played to perfection on the Friends episode, The One with the Blackout. It took him nearly choking on someone else’s gum, and having Victoria’s Secret model Jill Goodacre save his life, to find his voice. But through the awkward silence, Chandler’s exploding thoughts dished more comedic banters than a stand-up comedian. There’s just one word for his final expression after she pecks him in the last scene— Perfection!

Bonus points for snagging an Emmy nod! Friends season 8, episode 13 remains one of Matthew Perry’s undisputed best episodes in the 1994-released sitcom. The episode titled The One Where Chandler Takes a Bath featured the iconic bathtub scene where Monica persuades Chandler to enjoy a bathtub bat with fragrance salt and candles. After resisting initially because it was too girly, Chandler eventually tried it out and became hooked. But his attempt to steal one more magical bath session for himself did not pan out well. Even worse, the other five stumbled in on him in the bathtub and had a full-on conversation about Rachel’s (Jennifer Aniston‘s) baby, ignoring his discomfort. The episode snagged Matthew his only Emmy nomination for his role in Friends, with the bathtub scene as its climax.