A look back at Matthew Perry’s best moments as Chandler Bing on Friends

Actor Matthew Perry died Oct. 28 from an apparent drowning at the age of 54, sending shockwaves across Hollywood.

Though Perry had a number of memorable roles under his belt, he was most beloved for his role as the sardonic and quick-witted Chandler Bing on the hit 1990s sitcom Friends, the NBC juggernaut that propelled Perry and costars Courteney Cox, Jennifer Aniston, Lisa Kudrow, Matt LeBlanc, and David Schwimmer into superstardom.

In his 2022 memoir Friends, Lovers, and the Big Terrible Thing, the late actor recalled his instant connection to the character after reading the script. "It was as if someone had followed me around for a year, stealing my jokes, copying my mannerisms, photocopying my world-weary yet witty view of life," Perry wrote. "It wasn't that I thought I could play 'Chandler;' I was Chandler."



Below, EW revisits some of Perry's best moments as the transponster.

The one where Chandler helps pivot a couch


After Rachel (Aniston) helps Ross (Schwimmer) shop for a new couch for his apartment, the frugal Ross decides to forego delivery charges and carry the piece of furniture three blocks to his pad — hesitant Rachel in tow. Transporting the couch up the narrow staircase, however, proves to be problematic, so Ross instructs Rachel to hunt down some backup in the form of Joey (LeBlanc), but since he's available, she brings Chandler instead. ("Chandler? You brought Chandler? The next best thing would be Monica!") As the trio work to get the couch upstairs, Ross continually screams to "Pivot! Pivot! Pivot!" An exasperated Chandler yelps at Ross to "Shut up! Shut up! Shut up!" ("The One With the Cop," Season 5, Episode 16)

The one where Chandler proposes to Monica


After Chandler tries to surprise Monica (Cox) by pretending he never wants to get married, things go haywire. He emotionally bares it all to Richard (Tom Selleck) before coming home to find their apartment full of candles and Monica waiting for him. She drops to one knee to propose, but she's overcome. He kneels too, trying to take over but is equally verklempt. "You make me happier than I ever thought I could be," he manages to say. "And if you let me, I will spend the rest of my life trying to make you feel the same way." It's one of the most swoonworthy proposals in pop culture history — and that's in large part because of Perry's vulnerability. The actor was hysterically funny in an ensemble stacked with comedy greats, but it was his humanity that allowed him to move Chandler from winking wing-man to leading romantic hero. Nowhere is that more touching or deeply felt than in this tear jerking proposal. ("The One With the Proposal, Part Two," Season 6, Episode 25)

The one where Chandler tells Monica he loves her while she has a turkey on her head


After Monica tells Chandler the truth about how he lost his toe, she tries to cheer him up by putting a turkey on her head, complete with sunglasses and a hat. His grouchy mood is quickly dispelled with a laugh and an offhand, "This is so great, I love you." Monica slow turns in response as Chandler panics. Perry plays the quiet admission (a contrast to romantic grand gestures) with a comfort that underscores the chemistry of the Monica-Chandler pairing. He tries to undo his slip, even though Monica and all of us watching know he meant it. This moment showcases the subtlety of Perry's work and effortlessly funny line delivery across 10 seasons. ("The One With All the Thanksgivings," Season 5, Episode 8)

The one where Chandler and Phoebe attempt to seduce each other


When Phoebe (Kudrow) and Rachel find out about Chandler and Monica's secret romance, the two hatch a plan to get the pair to confess to the relationship. Joey, relieved that he no longer has to keep it a secret, proposes that the gang confront the couple, but the girls instead put a plan in motion for Phoebe to flirt with Chandler. It doesn't take too long for Chandler and Monica to catch on to the fact that their friends know that they know that they know, putting in motion a chaotic game of seduction to see who cracks first. ("The One Where Everybody Finds Out," Season 5, Episode 14)

The one where the TV Guide arrives for Chanandler Bong


Monica and Rachel wager their apartment during a game of trivia against Chandler and Joey, who believe that they know the girls better than the girls know them. With Ross as judge and quiz maker, the stakes become higher when the girls ask the guys to get rid of their pet duck and rooster should they win. Fine! As long as the girls agree to trade apartments should the guys emerge victorious. It's hard to choose from the standout moments, including the girls having no idea what Chandler's job is (a recurring gag on the show — and no, the correct response is not transponster!), but one particularly memorable moment involves Rachel incorrectly answering that the TV Guide arrives to the boys' apartment under Chandler's name. The correct response? Miss Chanandler Bong. ("The One With the Embryos," Season 4, Episode 12)

The one where Chandler gets stuck in an ATM vestibule with model Jill Goodacre


One of Chandler's first featured storylines, Perry proves why his talents elevated Chandler from a supporting figure to a series lead. When a citywide blackout traps Chandler in an ATM vestibule with model Jill Goodacre, Perry has to deliver much of his performance through his physicality, his thoughts played in voiceover — his discomfort exposed in a subtle turn of his head as he mentally debates whether he's in a vestibule or an atrium. His goofy approach toward Jill and subsequent retreat has rom-com energy, while also possessing plenty of his signature awkward sweetness. His self-deprecating voiceover's contrast with his physical humor makes these early scenes memorable, from his phone call to Joey through gritted teeth to his accidental gum spitting. When Chandler chokes on chewing gum and Jill saves his life, we understand Perry's physical comedic timing is as acute as the verbal alacrity he established from the pilot. ("The One With the Blackout" Season 1, Episode 7)

The one where Chandler and Rachel eat cheesecake off the floor


Rachel and Chandler very rarely got to share a storyline that revolved around the two of them, but Aniston and Perry make the most of their partnership here. After Mrs. Braverman's cheesecake is mistakenly delivered to their apartment, Chandler and Rachel eat it and become obsessed, devising increasingly absurd justifications for being "dessert stealers." Things escalate when the cheesecake ends up on the floor and Rachel and Chandler get down on their hands and knees with their forks. It's one of Chandler's more absurdist storylines and Perry lets loose with lines like "I'm taking it back" and his mock empathy at Rachel's cheesecake spill. His zany energy here makes us wish that he and Aniston shared more one-on-one screen time. ("The One With All the Cheesecakes," Season 7, Episode 11)

The one where Chandler kisses all the girls goodbye


Perry gets the punchline in this episode's cold open as he deadpans "I've had a very long, hard day," when Joey walks in on him in a bubble bath with a glass of wine (Monica is hiding beneath the water). But things get even more wacky when Chandler accidentally kisses Monica goodbye in front of Rachel and Phoebe. To cover it up, Chandler then kisses Rachel and Phoebe on the lips as well. The way Perry yells "Pheebs" and then practically skips out of the room is the stuff of comedic genius. He has to double down when the girls walk in on him and Monica making out, planting messy, prolonged kisses on them both. It's the commitment to the bit, both in the context of the story and in the acting choices, that make it one of the show's funniest moments. ("The One With All the Kissing," Season 5, Episode 2)

The one where Chandler stays in a wooden box


Chandler does his best to deny his feelings for Joey's new girlfriend Kathy (played by Paget Brewster), but the two are drawn together like magnets. During Kathy's birthday, it's Chandler who swaps Joey's gift (a pen) for a more meaningful one (a special edition of her favorite childhood book The Velveteen Rabbit), and Kathy knows this. The two resolve not to act on their feelings so not to hurt Joey, but later share a passionate kiss, which leaves Chandler racked with guilt. Determined to earn Joey's forgiveness, Chandler agrees to stay in a wooden box all of Thanksgiving. ("The One With Chandler in a Box," Season 4, Episode 8)

The one where Chandler is duped by a jaded Susie, played by Julia Roberts


While on set for a movie starring Jean-Claude Van Damme and Ross' former pet monkey Marcel, Chandler runs into a woman named Susie (played by Julia Roberts, Perry's real-life partner at the time) he knew in the fourth grade. She flirts with Chandler and asks him out on a date — but the poor chum is unaware that Susie is still scorned by a traumatic experience in grade school, when a young Chandler lifted up her skirts and made her the laughing stock of school. Over dinner at a fancy restaurant, they rendezvous in the bathroom, where Susie tricks Chandler into stripping naked so she could run off with all of his clothes and turn the tables on the humiliation. ("The One After the Superbowl: Part 2," Season 2, Episode 13)

The one where Chandler travels to Yemen to avoid Janice


While out and about with Rachel, Chandler runs into his overbearing ex-girlfriend Janice (Maggie Wheeler), who reveals to him that she's recently divorced. As it turns out, Janice still has feelings for Chandler. Unable to cut her loose, Chandler concocts a lie about having to move to Yemen for work. Desperate to spend the little time that they have left together, Janice buys Chandler luggage for the big move and even insists on accompanying him to the airport, where he attempts to obtain a fake ticket before ultimately buying one — and an expensive one at that. Still unable to shake the lovelorn Janice, who refuses to leave until he boards the plane, Chandler reluctantly gets on the flight and makes his way to the Middle East. ("The One With All the Rugby," Season 4, Episode 15)

The one where Chandler convinces Erica to let him and Monica to adopt her baby


After lying to a pregnant Erica (Anna Faris), Monica and Chandler are on the verge of losing the baby they so desperately want. But Chandler chases after Erica, apologizing for their lies and explaining why she should still choose them to adopt her baby. First, he sings Monica's praises before nearly breaking down admitting his fertility issues. Perry delivers a moving speech about Monica's innate motherhood — and it works! He pivots nimbly from his emotional words to the sweet and funny victory dance he gives Monica as he tells her the happy news. It's Chandler in one of his purest moments. ("The One With the Birth Mother," Season 10, Episode 9)

The one where Chandler has a work laugh and is also named Toby


Before their secret romance is found out by their best pals, Monica accompanies Chandler to an office party in a season 5 episode ("The One With Chandler's Work Laugh"), where she learns that her beau has an off-putting work laugh he employs around his new boss Doug. Another episode in season 8 ("The One With Rachel's Date") also sheds light on Chandler's kooky work dynamics. Ross learns that Chandler's coworker Bob (Chris Parnell) has been calling him Toby for several years. Chandler explains that he was unable to initially correct him as he was in a hurry to get somewhere, and Bob later asked "Toby" if he wanted a donut, and Chandler wanted a donut and therefore answered as Toby. It would be much too humiliating to correct Bob now, Chandler explains — especially after Bob learned that a Chandler had blocked him from a potential promotion.

The one where Chandler wins over Monica's parents


Despite knowing them for years, Chandler has never been able to win the approval of the Gellers. Ross realizes why when Judy (Christina Pickles) makes a remark about Chandler being "stoned." He reveals that he blamed Chandler for his own pot smoking back in their college days. It leads to Ross and Monica one-upping their tattle tales, but the kicker comes when Judy thanks Chandler for sticking by Ross during his "drug problems." "You're a wonderful human being," she tells him, which evokes a look that is somewhere between shock and smug vindication. His ready embrace of the Gellers is funny, yes, but it plays because it's indicative of Chandler's true core need — to be loved by those around him. ("The One Where Ross Got High," Season 6, Episode 9)

The one where Chandler reads his wedding vows


Monica and Chandler's wedding could not BE more of a mess, but their vows are the stuff of fairy-tales, particularly when Chandler goes off script. "Monica, I thought this was going to be the most difficult thing I ever had to do," he starts. "But when I saw you walking down that aisle, I realized how simple it was. I love you; any surprises that come our way, it's okay because I will always love you. You are the person I'm meant to spend the rest of my life with. You want to know if I'm sure?" He answers her by sealing it with a kiss. Perry's solid, surefooted delivery makes the moment all the more romantic, as we see his usual sarcastic, frenetic energy calmed by a man never more sure of anything in his life. ("The One With Monica and Chandler's Wedding," Season 7, Episode 24)

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