Matthew Perry’s 10 Most Iconic Chandler Moments On Friends

Throughout 10 seasons and 200-plus episodes, Friends star Matthew Perry kept audiences laughing as Chandler Bing. Armed with sarcastic wit to his signature intonations, he used humor to combat discomfort, delivering some of the NBC sitcom’s most iconic one-liners from 1994 to 2004.

“Hi, I’m Chandler. I make jokes when I’m uncomfortable,” he quipped in an oft-memed Season 6 scene. And Perry’s all-time favorite Chandler quote couldn’t be any funnier. “You have to stop the Q-tip when there’s resistance,” as his character joked after Joey (Matt LeBlanc) made one of his classic airhead comments.

When news broke that Perry died on Oct. 28 at 54 years old, fans looked to Chandler’s relatable comedy once again to soothe their heartbreak. As celebrities and viewers alike flocked to social media to share their favorite memories of Perry, several classic Chandler scenes also began recirculating online. (For those re-watching their favorite Friends episodes on Max, the streamer added a tribute card to Perry at the start of each season.)

Below, revisit some of Perry’s most iconic Friends moments that are comforting fans in the wake of this sad loss.

His Model ATM Mishap(s)

During a New York City power outage in Season 1’s seventh episode (“The One With the Blackout”), Chandler gets trapped in an ATM vestibule with Victoria’s Secret model Jill Goodacre.

True to form, Perry’s character awkwardly tries to impress her. After several mishaps, the beauty eventually uses the Heimlich maneuver to save him from choking on used chewing gum. Perry’s masterful physical comedy was further punctuated by the fact he delivered most of his lines (his inner thoughts) in a voiceover.

Julia Roberts’ Revenge

Continuing the theme of being stuck in an embarrassing situation, Season 2’s “The One After the Superbowl: Part 2” features guest star Julia Roberts as Susie “Underpants” Moss, an old elementary school classmate with a score to settle. After luring him into a restroom during a dinner date, Susie gets her long-awaited revenge for a fourth-grade prank by leaving Chandler trapped in a stall wearing only “panties.”

Fun fact: Perry revealed in his 2022 memoir, Friends, Lovers and the Big Terrible Thing, that he and Roberts were dating in real life at the time.

Being A “La-Z-Boy” With Joey

After Joey (Matt LeBlanc) gets a big Days of Our Lives paycheck in Season 2’s “The One Where Ross And Rachel... You Know,” he invests in a big screen TV and two leather recliners.

He and Chandler get a little too comfortable, though, and don’t move for days. They even devise a scheme to have their takeout delivered to Monica (Courteney Cox) and Rachel’s (Jennifer Aniston) apartment, forcing them to hand-deliver the food across the hall.

Chandler In A Box

Hilarity ensued in Friends Season 4’s Thanksgiving episode (“The One With Chandler in a Box”) when Joey “sentenced” Chandler to spend six hours in a wooden crate, as punishment for kissing his girlfriend, Kathy (Paget Brewster).

“You can’t tell, but I’m easing the tension by mooning you guys,” Chandler announces from inside the box during the crew’s holiday meal, proving Perry didn’t even have to physically appear on screen to score major laughs.

His Escape To Yemen

The running gag is that nobody knows what Chandler’s job is, but on-and-off girlfriend Janice (Maggie Wheeler) takes a particular interest in Season 4’s “The One With All the Rugby.”

To avoid breaking her heart, he lies about being transferred to Yemen for work (“15 Yemen Road, Yemen,” to be exact). The ruse goes way too far, though, when Janice — who can’t figure out why his friends don’t seem to care he’s leaving — insists on taking him to the airport. After trying everything to fake his departure, Chandler is so desperate to escape his ex that he drops $2,100 on the plane ticket, announcing, “Well, then I guess I’m going to Yemen!”

His ’80s Flashback Hair

Hardly his only flashback hair-don’t, Chandler’s ’80s A Flock of Seagulls style in Season 5’s “The One With All the Thanksgivings” may be the most hilarious.

As the title suggests, the episode revisits past holidays, including when Ross (David Schwimmer) brought college roommate (and lead singer of their band) Chandler to the Geller family home for Thanksgiving 1987. In Season 2, he also mentioned that his “Flock of Seagulls haircut was tickling” someone’s chin all the way back in 1982.

Seducing Phoebe

While going to great lengths to keep his budding romance with Monica under wraps, Chandler makes a hilariously reluctant attempt to “seduce” Phoebe (Lisa Kudrow) in Season 5’s “The One Where Everybody Finds Out.”

But because they didn’t know that they knew that they already knew (or something like that) about the fling, Phoebe plays along, with both seeing who can hold out the longest. After an awkward kiss, Chandler caves and confesses that he loves Monica — and she’s even hiding in the bathroom to hear him use the l-word for the first time.

Monica’s Proposal

Season 6’s aptly titled “The One With the Proposal” had fans celebrating (after shedding some happy tears, of course) when Chandler and Monica both get down on one knee. After Monica surprised him with a candlelit apartment, he takes over when she can’t get through her proposal speech without sobbing.

Though Chandler was the sarcasm king, Perry won hearts here with his (tear-filled) sensitive performance while still inspiring a few laughs.

The Cheesecake Bandits

Chandler and Rachel turn to the life of crime in Season 7’s “The One With All the Cheesecakes.” After a cheesecake was accidentally delivered to Chandler’s door, he and Rachel become so obsessed that they steal a second one from outside their downstairs neighbor’s door.

Their rock bottom arrives when Rachel drops her half on the hallway floor — and knocks Chandler’s out of his hands for taunting her — prompting the pair to grab their forks and begin eating it directly off the ground.

Chandler Couldn’t Smile

In Season 7’s fifth episode, “The One With the Engagement Picture,” Monica discovers that Chandler can’t smile normally, ahead of their professional photo shoot for a local newspaper announcement. Despite Monica’s best teaching efforts — and multiple trips to the portrait studio — Chandler just can’t seem to get the hang of smiling without looking like a “creep” or a “moron.”

Joey eventually replaces him in the final shot, but the episode puts Perry’s physical comedy chops at center stage once again.