Matthew Perry’s 10 best moments as Chandler in Friends

On Oct. 28, 2023, the world truly lost an amazing person, actor, and comedian. Matthew Perry died at the age of 54 after he was found unresponsive in his hot tub. However, medical examiners are still working to determine what the exact cause of death is.

The beloved Friends actor struggled with addiction for years. It’s so sad that he came out with his book in November 2022, shared his difficult journey with everyone, got clean, and now has unexpectedly passed. We will definitely miss him. In his memoir, Perry shared that he wanted to be remembered as someone who helped people. Because he could relate to others who went through similar situations as he did. Well, that’s definitely one of the things we’re going to remember him for.

The actor was also a comedic genius, and that was showcased the most on Friends (streaming on Max). Many times, he would ad lib certain lines or was asked to write the jokes for his character Chandler. And they’d make the final cut! That’s how quick and witty he was. A true talent! With his untimely passing, we’re taking a look back at some of Matthew Perry’s most memorable moments as Chandler. There’s too many to list here, but we’ve rounded up 10 of our favorites! Here’s a list, and we go more in-depth into some of these moments further below:

1. Chandler tries to stop smoking (season 3 episode 18)
2. Chandler is handcuffed (season 4 episode 3)
3. Chandler kisses Monica, Rachel, and Phoebe goodbye (season 5 episode 2)
4. Phoebe vs Chandler in seducing game (season 5 episode 14)
5. Chandler makes up a game to give Joey money (season 6 episode 6)
6. Chandler trying to propose to Monica (season 6 episodes 24 and 25)
7. Chandler can’t smile for professional photos to announce he and Monica’s engagement (season 7 episode 5)
8. Ross: “I went to that tanning place your wife suggested.” Chandler: “Was that place, the sun?” (season 10 episode 3)
9. “What did I marry into?” (season 10 episode 11)
10. Matthew Perry gets the last line of the series – Rachel: “Ok, should we get some coffee?” Chandler: “Sure. Where?” (season 10 episode 18)

Best Chandler moments on Friends

We don’t go in-depth for all the moments we listed above. I’m sure you avid Friends friends, like me, will immediately remember the references just from reading the list. The ones we’ve shared below are some of my favorites because it shows how funny and talented Perry is, portrays Chandler’s character growth and sweet side when it comes to Monica, and how he’s a great best friend to Joey. Read on below!

The one where Chandler tries to stop smoking – season 3 episode 18

In “The One With the Hypnosis Tape,” Rachel tries to help Chandler stop smoking by giving him a hypnosis tape to listen to while he’s sleeping. However, the recording is catered to women, which leads to a hilarious episode of unexpected side effects. Chandler starts acting like a woman – from wearing chapstick, to giving Monica advice about her date, and being overly excited when her date arrives. And it’s Perry’s wonderful acting that really brings these scenes to funny fruition!

The one where Chandler is handcuffed – season 4 episode 3

In “The One With The Cuffs,” Chandler starts dating Rachel’s boss, Joanna. But she has a wild side, which leads him into some trouble – getting handcuffed in her office without his pants on. He asks Rachel to help him, but in a hilarious scene she realizes that if she lets him go, her boss will know Rachel did so and fire her. I don’t know what it is, but the way Perry portrays Chandler’s face, the sarcastic lines, and then his physical comedy of having to jump with Rachael dragging him to the filing cabinet to recuff him just makes me laugh every time.

The one where Chandler is a true friend – season 6 episode 6

Throughout the series, Chandler really proves how good of a friend he is to Joey. He constantly lends him money, pays for acting classes, and more. It seems like he was also the one mostly handling the bills. But as Chandler decides to move in with Monica, this puts a strain on Joey. Though he doesn’t want Chandler to continue helping him pay for things in the apartment, which makes Chandler feel guilty. And so, Chandler comes up with the game of “Cups” to trick Joey into “winning” money to secretly help him out. The point of this is that it shows how much Chandler cares about his best bud. He went through all of that just so he doesn’t have to worry about Joey. And it’s really one of the most likable traits about Chandler.

The one where Chandler tries to propose – season 6 episodes 24 and 25

We, as well as Monica of course, know that Chandler had commitment issues. However when he started to fall in love with Monica, that all went away. That is until he got scared before the wedding. But, that’s a different story. Before that, Chandler was ready to take that next step in their relationship and propose to Monica.

His plans get thrown off when none other than Richard pops up at the restaurant at the wrong moment with a date of his own. And so to throw her off, Chandler starts to act like he never wants to get married. And of course, this is when Richard goes back to see Monica and tells her he still loves her.

Thinking he’s lost his shot with the woman he loves, Chandler rightfully freaks out and is devastated. But Monica had a surprise of her own. She gets down on one knee first, but the two sort of end up proposing to each other. It makes my heart melt every time! And these two back-to-back episodes really showed Chandler’s emotional growth and how far he’s come into becoming an adult in a committed relationship. I love it!

The one where Matthew Perry gives us the last laugh – season 10 episode 18 (series finale)

The final episode of Friends was truly emotional. It was bittersweet for us fans, but also for the cast who’d been working together for 10 years. But even as we’re feeling sad that such a great series is coming to an end, Matthew Perry still managed to make us laugh until the very end.

In the final scene, Rachel asks if Chandler and Monica have time to grab coffee with the group before they head to their new house with their babies. Chandler responds with, “Sure. Where?” in a hilariously sarcastic line. Of course we all know that there’s only one place for this group to go. And that’s Central Perk.

Though in a moment everyone is emotional, both Chandler and Perry make us laugh. And it truly does come down to the actor because the “where?” line wasn’t in the script. It was Perry who came up with it! Though Perry himself didn’t feel good that day, he managed to do what he did best, and got a laugh out of everyone before the episode comes to a final close. And for that, we’ll always appreciate Perry for what he brought to the show, and who he was as a person.

Check out all of Matthew Perry’s best moments as Chandler on Max, as all 10 seasons of Friends are streaming on the platform.