In his role as Chandler Bing, Matthew Perry was the master of sarcastic comments and witty jokes. His delivery was always spot-on, and his charm was annoyingly sweet and funny. Friends would not be the same without Perry’s Chandler Bing.
Here are the 15 episodes of Friends where Matthew Perry shines.
1. The One With the Blackout
Season & Episode: Season 1, Episode 7
Date Aired: November 3, 1994
In this episode, Chandler is stuck in an ATM with a supermodel because of a city-wide blackout. As he tries to flirt with the celebrity, Matthew’s voice-over of Chandler’s thoughts is hilarious and painfully cringe-y at the same time.
His acting performance is top-notch, though, and you’ll feel embarrassed for him.
2. The One Where Heckles Dies
Season & Episode: Season 2, Episode 3
Date Aired: October 5, 1995
Mr. Heckles is the grumpy neighbor who always scolds Rachel and Monica for being noisy. When he passed away, he left all his earthly possessions, all of which were junk, to the girls. While going through Mr. Heckles’ things, Chandler discovers eerie similarities with him.
Perry brilliantly acted out Chandler’s fear of ending up alone like Heckles. His eyes and non-verbal gestures showed his desperation to find someone to be with.
3. The One Where Eddie Won’t Go
Season & Episode: Season 2, Episode 19
Date Aired: March 28, 1996
Eddie becomes Chandler’s new roommate after Joey moves out. Chandler quickly realizes Eddie is unhinged and creepy, so he tries to kick him out.
Throughout the episode, Perry portrays Chandler as disturbed and freaked out by Eddie’s strange behavior, like his mood swings and watching Chandler sleep.
4. The One Where No One’s Ready
Season & Episode: Season 3, Episode 2
Date Aired: September 26, 1996
Ross struggles to rally the gang for his museum gala, but no one cooperates. Chandler and Joey argue over who has the right to sit on a specific chair, which seems ridiculous.
Matthew Perry was a joy to watch with his contagious energy. His delivery of the line “Get up!” in different intonations is impressive.
5. The One Where Chandler Can’t Remember Which Sister
Season & Episode: Season 3, Episode 11
Date Aired: January 9, 1997
Heartbroken and drunk, Chandler tries to forget Janice by hooking up with one of Joey’s seven sisters. The next morning, he can’t recall which sister he fooled around with, which makes him fear Joey’s wrath even more.
Matthew Perry entertains as he shifts from a lovably broken-hearted drunk to a panicked friend. His clumsy antics are charming and genuine.
6. The One With the Hypnosis Tape
Season & Episode: Season 3, Episode 18
Date Aired: March 13, 1997
This episode of Friends has an outdated joke about homosexuality: Chandler tries to quit smoking by listening to a hypnosis tape Rachel recommends. The tape makes him act more feminine, which makes people think he’s gay.
Matthew effortlessly brings out his feminine side for the role. Wrapped in a towel, he skillfully applies lip gloss while smacking his lips. His portrayal isn’t overly girly but also isn’t lacking in authenticity.
7. The One With the ‘Cuffs
Season & Episode: Season 4, Episode 3
Date Aired: October 9, 1997
Rachel discovers Chandler handcuffed in her boss Joanna’s office. It turns out Chandler is dating Joanna and got chained to the desk while she was in a meeting. Throughout the episode, Chandler begs to be released while Rachel fears getting fired if she frees him.
Seeing Matthew Perry in handcuffs will make you roll on the floor laughing. The funniest moment, where Perry accidentally hit his head while pulling a drawer, was actually not in the script.
8. The One With Chandler in a Box
Season & Episode: Season 4, Episode 8
Date Aired: November 20, 1997
To make amends with Joey after falling in love with his girlfriend, Chandler agrees to stay inside a wooden box for six hours to prove their friendship’s worth.
It’s tough to be funny without being visible in the scene. But Matthew Perry pulls it off, gaining sympathy with just one finger showing from the box.
9. The One With All the Rugby
Season & Episode: Season 4, Episode 15
Date Aired: February 26, 1998
Chandler doesn’t like breaking up, and even though he wants to end things with Janice, he doesn’t want to hurt her. So, he decides to tell her he’s been reassigned to Yemen.
Matthew Perry clearly portrayed Chandler’s desperation to escape Janice. His irritated and frustrated expressions add unexpected humor to his actions.
10. The One Where Everybody Finds Out
Season & Episode: Season 5, Episode 14
Date Aired: February 11, 1999
After Rachel and Phoebe learn about Monica and Chandler’s relationship, a battle begins. Phoebe tries to seduce Chandler, who pretends to fall for her advances.
Perry displays his acting skills by portraying Chandler as awkward yet confident when dealing with Phoebe’s advances. When he finally admits his love for Monica, his expression is sincere and convincing.
11. The One With Rachel’s Sister
Season & Episode: Season 6, Episode 13
Date Aired: February 3, 2000
With Monica sick at home, Chandler takes on the responsibility of caring for her and making sure she gets enough rest. Perry was extra funny in this episode as he raised mockery and sarcasm to another level.
Courtney Cox also shines, matching Perry’s sarcasm with funny lines and actions.
12. The One With the Proposal (Parts 1 & 2)
Season & Episode: Season 6, Episodes 24 & 25
Date Aired: May 18, 2000
When Richard interrupts Chandler’s proposal plan to Monica, Chandler pretends to hate the idea of marriage. Matthew Perry’s sudden change from arrogance to fear of losing Monica is remarkable.
His comedic timing and line delivery were perfectly aloof and fit the scene’s vibe.
13. The One With Monica and Chandler’s Wedding (Parts 1 & 2)
Season & Episode: Season 7, Episodes 23 & 24
Date Aired: May 17, 2001
Monica and Chandler’s wedding is a momentous event for the gang, but it’s not all happiness for Chandler, who gets cold feet.
Perry captures the overwhelmed look of a groom soon to be wedded, from running away to lighting up a cigarette to hyperventilating.
14. The One With the Birth Mother
Season & Episode: Season 10, Episode 9
Date Aired: January 8, 2004
This episode highlights Matthew Perry’s versatility as an actor. Departing from his usual goofy character, he delivers a deeply emotional scene.
His heartfelt monologue about Monica had some jokes in between that still suit his character.
15. The Last One
Season & Episode: Season 10, Episode 17
Date Aired: May 6, 2004
In the final episode, Perry stays true to his character. The show concludes with Chandler having the last word. When Rachel suggests getting coffee, his response “Where?” is the most “Chandler-esque” reply ever.
Chandler’s blend of sadness and sarcasm suits the scene perfectly. It’s the ideal ending for this beloved and iconic character.