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Friends: Best Matthew Perry Episodes

Friends star Matthew Perry recently announced that his memoir, Friends, Lovers, and the Big Terrible Thing, will be published in November. With a title like that, he’s bound to be sharing some behind-the-scenes goodies from our favorite generation-defining sitcom. Along with co-stars Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, and David Schwimmer, Perry is responsible for many iconic moments throughout Friends‘ 10-season run. It’s a difficult task to narrow down his best episodes so forgive us if we forgot your favorites, but these are definitely some of Chandler’s finest half-hours, season by season.

RELATED: Oscar-Winning Guest Stars on Friends Ranked


Season One — “The One With the Blackout”

The One With the Blackout

Chandler Bing stole our hearts from the very first episode with his comedic timing and physical expressions, bringing more than a few giggles from the live studio audience (and those of us at home who spent every Thursday night with our favorite Friends). But some of Chandler’s funniest moments came in the blackout episode when he was stuck in an ATM vestibule with supermodel Jill Goodacre. Most of the laughs come from Chandler’s thoughts, delivered via voiceover. For example, when he turns down a piece of gum from Jill, and then says, “On second thought, gum would be perfection.” In his mind, he’s thinking, “Gum would be perfection? I loathe myself.” He then proceeds to try to look cool and aloof by blowing a bubble, only to accidentally spit the gum out, pick it back up, and put it back in his mouth, only to realize it’s someone else’s gum. And then he’s choking! His voice delivering these lines is nothing short of genius — and hilarious.

Season Two — “The One Where Heckles Dies”

The One Where Heckles Dies

Chandler shows his more vulnerable side in this Season 2 episode, when Monica and Rachel’s downstairs neighbor, the cranky Mr. Heckles (Larry Hankin), dies suddenly, leaving the girls all of his belongings. When the gang is cleaning up the mess in his apartment, Chandler discovers he had a lot more in common with Mr. Heckles than he realized — they were both voted Class Clown, and they both turned down a number of attractive women because of minor flaws, like big gums or in Chandler’s case, large nostrils. Over the course of the episode, Chandler goes from panicking that he’s going to die alone to realizing that he doesn’t have to completely follow in Heckles’ footsteps. He can make his own way in the world. He even decides to date a woman from his office who he’s avoided asking out before now, because of her large head. The credits scene, though, is hilarious, when he’s thinking to himself that his head looks like a golf ball next to hers. Classic Chandler.

Season Three — “The One Where Chandler Can’t Remember Which Sister”

The One Where Chandler Can't Remember Which Sister

Still somewhat in shock that his ex (“Oh. My. God.”) Janice (Maggie Wheeler) is married with a child on the way, Chandler drowns his sorrows in Jell-o shots at Joey’s birthday party and ends up fooling around with one of Joey’s sisters. The problem is, he can’t remember which sister. With Ross’s help, he decides to go over to the Tribiani house and ask for Mary Angela, the one he made out with, in hopes of figuring out which one she is. His plans go awry, of course, when all of the sisters are there for a family dinner. He has some really great lines here and probably deserved the punch to the face delivered by the toughest of Joey’s sisters, Cookie.

Season Four — “The One With the Embryos”

The One With the Embryos

It was in this classic episode that the name Chanandler Bong was first revealed when Ross fashions a trivia game (complete with the lightning round!) to try to decide who knows their friends better: Chandler and Joey or Monica and Rachel. The game is one of the best Friends sequences in all 10 seasons, from the TV Guide being delivered to Ms. Chanandler Bong to the phenomena that scares the bijesus out of Chandler: Michael Flatley, Lord of the Dance. (“His legs flail about as if independent from his body!”) And, the mystery of what exactly Chandler’s job is begins. Spoiler: he’s not a transponster.

Season Five — The One Where Everybody Finds Out

The One Where Everybody Finds Out

Another great Friends-ism was born on this episode: “They don’t know that we know that they know we know.” When Phoebe sees Monica and Chandler “doing it,” the whole messer vs. messee game begins, and it leads to some hilariously awkward interactions between Phoebe and Chandler. Kudrow is fantastic in this episode, but so is Perry, especially when he invited Phoebe over to “feel his bicep… and maybe more.” His delivery of lines like, “It’s very nice,” referring to Phoebe’s bra, and “I’m very excited we’re going to have all the sex” make this one of Chandler’s best episodes. As a bonus, it’s also when he tells Monica he loves her in a very sweet moment.

Season Six — “The One Where Chandler Can’t Cry”

The One Where Chandler Can't Cry

Though the season-ending engagement to Monica is always a goodie, this one is also a fantastic use of Perry’s wit and impeccable comedic timing. When Monica finds out that he hasn’t cried since he was a child, she becomes desperate to find something that will make him tear up. One of his best lines comes in this episode: “Well, that makes me feel all warm inside my cold tin chest.” Finally, he sheds his first tears in decades when he gets sad that Ross and Rachel can’t ever seem to make it work between them, even though it’s so clear to everyone that they’re meant to be together. Of course, once he starts to cry, every tiny thing makes him burst into tears.

Season Seven — “The One With the Engagement Picture”

The One with the Engagement Picture

Monica decides that she and Chandler should have their engagement photo in the newspaper, she discovers that Chandler is not very photogenic — and that’s putting it kindly. Even when he’s smiling or laughing naturally, as soon as the camera starts to click, his smile morphs into a hilarious grimace. It’s some of the best physical comedy showcased by Perry throughout Friends‘ 10-year run. It’s impossible not to laugh at his “smile” in the photos, even as many times as it happens throughout this episode.

Season Eight — “The One With the Halloween Party”

The One with the Halloween Party

Monica hosts a Halloween party and ends up getting Chandler a pink bunny costume. The first moment you see him as a big fluffy pink bunny is hilarious. Monica, on the other hand, looks amazing as Catwoman… but when doesn’t she? She’s the one who picked the costume for Chandler and claims she couldn’t find anything other than a pink bunny. “It was the pink bunny or no bunny at all,” she tells him. “Always no bunny at all!” he responds in his usual deadpan voice. When Ross shows up dressed as “Spudnik,” a potato and satellite, naturally, Chandler makes his classic jokes about how he looks like a doody, saying later that Ross looks “a little flushed.” The arm-wrestling match between Ross and Chandler is epic, and the way Chandler still tries to prove himself to Monica, again and again, is so sweet.

Season Nine — “The One With Ross’s Inappropriate Song”

The One with Ross's Inappropriate Song

While this episode is titled after Ross making Baby Emma laugh for the first time by rapping “Baby Got Back,” it’s also a wonderful episode for Chandler to once again face his insecurities over Monica’s relationship with her old flame, Richard (Tom Selleck). When he and Joey find out Richard’s apartment is for sale, they book a viewing with a real estate agent and Chandler’s insults (mostly to do with Richard’s mustache) are non-stop. Until he finds a video on the shelf with Monica’s name on it. Chandler doesn’t want to watch it, but can’t help himself. It’s heartwarming to see that Monica is finally over Richard, and truly in it for the long haul with Chandler.

Season Ten — “The One Where Estelle Dies”

The One Where Estelle Dies

The final season was full of changes for our six favorite New York City Friends, and this episode saw Monica and Chandler moving out of the city and into the suburbs. They’ve finally found their dream house, and find out at the last minute that there’s another buyer interested. Who else but Janice? Whereas Season 9 saw Monica finally letting go of Richard once and for all, this was Chandler’s chance to get closure with Janice as well. There are some truly great moments and a fond farewell to Janice — and life in the city, too.

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