Fun
Frisky
Nostalgic
Intense
Adventurous
Choked Up
Curious
Romantic
Weird
There was a while there on Friends where Chandler was the show’s central character. The Chandler/Monica relationship had taken over for Ross and Rachel as the driving force behind the show’s narrative, and Matthew Perry’s nervous, empathetic performance as Chandler put him front and center while Ross was busy going crazy and Joey was biding his time for that divisive Rachel storyline to kick in. And despite the plethora of gay-panic punchlines and placing bets on whether a given episode was to feature skinny Chandler or bloated Chandler, the character was featured in some of the show’s best moments.
We picked the 10 Chandler-iest episodes for you to stream as a kind of Chan Experience guided tour, from his friendship with Joey to his relationship with Monica to his career as a transpondster.
[You can stream Friends on Netflix.]
'The One With The Thumb' (Season 1, Episode 3)
One early Friends rule: Chandler’s smoking habit is always funny.You hardly ever get subplots about smoking anymore. And you especially don’t get characters talking about how much they love smoking. Chandler’s attraction to the ol’ cancer sticks is one of the best runners throughout the run of the show, and Chandler’s deep longing for his old habit are such a great character detail.
'The One With The Blackout' (Season 1, Episode 7)
The network-wide blackout that NBC used as a sweeps stunt for its Must-See TV Thursday lineup turned into one of the better episodes of Friends‘ first season. Chandler got stuck in an ATM vestibule with supermodel Jill Goodacre, but the real interaction on hand was between Chandler and his increasingly disgusted inner monologue.
'The One Where Heckles Dies' (Season 2, Episode 3)
Friends being a sitcom, you wouldn’t get somber character moments every week, but the episode where the friends’ cranky, strange older neighbor Mr. Heckles died gave the show a chance to peer into Chandler a bit; in particular his fear of becoming that cranky old man without anybody who loves him.
'The One After The Super Bowl' (Season 2, Episode 12)
Any episode featuring Julia Roberts is going to be memorable automatically. The stunt casting in this post-Super Bowl episode was aggressive, but Roberts was clearly the crown jewel. And they paired her with Chandler, for a sexy and scandalous storyline that ended up with Chandler wearing women’s panties (and nothing else) in a men’s room stall as part of the longest-gestating act of revenge since Oldboy.
'The One Where Chandler Can't Remember Which Sister' (Season 3, Episode 11)
Chandler and Joey’s super-close friendship was just begging for something to bust it up, and Chandler drunkenly sleeping with one of Joey’s sisters was just the thing. The extra special twist, of course, is right there in the title. Chandler can’t remember which of Joey’s sisters he slept with. Well, they all look really similar!
[Stream “The One Where Chandler Can’t Remember” on Netflix.]
'The One With The Cuffs' (Season 4, Episode 3)
Chandler starts sleeping with Rachel’s boss, which is bad enough. It gets way worse when fun sex games lead to Chandler being handcuffed, half-naked, in Rachel’s boss’s office. This episode is perfectly emblematic of what a disaster Chandler’s romantic life was before Monica.
'The One With All The Rugby' (Season 4, Episode 15)
While Ross was busy getting beaten all to hell in a rugby game, Chandler was busy trying to break up with Janice without breaking up with her. Which is where he got the brilliant idea to fake a job offer from Yemen. The Chandler/Janice relationship was a great well that the show returned to time and again, and watching Chandler panic as he tries to flee his boundary-pushing girlfriend is brilliant.
'The One With All The Thanksgivings' (Season 5, Episode 8)
The flashback to Chandler’s Miami Vice-obsessed college years ended badly — with his pinky toe severed after a kitchen mishap with Monica. Chandler’s legendary hatred of Thanksgiving was a great recurrent character beat, but this episode is most memorable for Chandler’s first “I love you to Monica.” That it comes while Monica is wearing a turkey on her head, complete with sunglasses and a fez, just makes it all the sweeter.
'The One With The Proposal' (Season 6, Episode 24)
The surprise success of the Chandler/Monica pairing at the beginning of season 5 reached its peak at the end of season 6, with what likely stands as the most romantic moment in the show’s history. (All the more romantic for the fact that Joey gets to take part, if you ask me.) Monica proposing, then having to stop because she got too tearful, then Chandler getting weepy himself — it’s the show at its utmost sentimental, but it’s so great.
'The One Where Chandler Takes a Bath' (Season 8, Episode 13)
It’s the Enya that makes it, really. The Chandler-Monica marriage could get a little squabbly in its domesticity, but their feud over who gets to take a bath is pretty consistently rewarding.
