Chandler's Best Episodes In Friends, Ranked

One of the things that makes "Friends" so great is that each member of the cast has plenty of chances to shine. Whether an episode focuses primarily on a certain character or just gives someone one great joke or moment, no one got short shrift across the series' 10 seasons. Chandler Bing (Matthew Perry) was (and is) no doubt a fan favorite, and he steals almost every scene he's in with a sarcastic remark or flawlessly executed one-liner. But some of the best moments of the show are the ones where Chandler is actually the intended center of attention.

With the shocking death of Matthew Perry in October 2023, revisiting Chandler's appearances on "Friends" has become extremely bittersweet. While Perry had mixed feelings about "Friends" being his primary legacy, there's little doubt that the show — and Chandler-centric episodes in particular — are where the majority of his fans have turned to both mourn and celebrate the brilliant comedic actor. Everyone has their favorite Chandler episodes, but these are the ones that we feel best represent him and Perry's excellent performance.

"Friends" follows a group of pals who, in some cases, have been friends since childhood. And they all spend a ridiculous amount of time together as adults. As a result, they all know a lot about each other — in some cases, probably far too much. So Chandler can't be blamed for taking it a little personally that none of his friends, not even best bud Joey (Matt LeBlanc), know what he does for a living. Not only do they not know his official job title, but they can barely put together more than a couple of words to describe what he does.

That's just one of the many hilarious aspects of the classic Season 4 episode "The One with the Embryos," where the gang participates in a trivia competition featuring personal questions about one another. What makes it a great Chandler episode in particular isn't just his hilarious indignation about nobody knowing his job, but all of the other delightful revelations about the character — from the fact that he's unsettled by Michael Flatley of "Lord of the Dance" fame to how his TV Guides are addressed to "Miss Chanandler Bong." If there is such a thing as deep Chandler lore, "The One with the Embryos" might be the most abundant source of it in the entire series.

It needs to be addressed upfront that the overall handling of Chandler's father (Kathleen Turner) on "Friends" has aged incredibly poorly. It was misguided at the time and has only become worse in retrospect. To the credit of series co-creator Marta Kauffman, she at least owns up to it. "Pronouns were not yet something that I understood," Kauffman told the BBC in July 2022. "So we didn't refer to that character as 'she'. That was a mistake."

Despite Chandler's negative (and at times outright mocking) reaction to his parent transitioning, the episode where they reconcile is one of his most touching. In the episode, Chandler and Monica (Courtney Cox) travel to Las Vegas to invite Chandler's estranged parent to their wedding. The scenes in Las Vegas where the two seem to finally take some long overdue steps toward mending their estranged relationship showcase Perry's often underrated dramatic chops beautifully. It also helps that Chandler is much more supportive after this episode.

Some shows are known for their Christmas specials, others for their Halloween episodes. But "Friends" ended up choosing Thanksgiving as the holiday that became the backdrop to some of its most memorable episodes each season. The one where Monica is literally wearing a turkey on her head when Chandler first tells her he loves her — Season 5's "The One with All the Thanksgivings" — is definitely a fan favorite and just missed our list.

Instead, we went with "The One with Chandler in a Box" as the more iconic Thanksgiving episode where Chandler plays an especially key role. Chandler and Joey's friendship is one of the sweetest in television history, so when something manages to come between them, it's always a big deal. In this case, it's Kathy (Paget Brewster), whom Chandler falls hard for despite her initially being Joey's girlfriend. Things get so messy with the love triangle that Joey threatens to move out of his and Chandler's apartment altogether over it. The result is Chandler locking himself in a wooden box and Perry getting to show off how funny — and how heartwarming — he could be even without relying on his trademark facial expressions and hand gestures to help sell his lines.

Though there was never a truly bad stretch of "Friends," it definitely felt as though the writers weren't quite sure what to do with most of the characters anymore in the last few seasons. One of the biggest examples of this was the misguided attempt to turn Rachel (Jennifer Aniston) and Joey into a romantic pairing, which became even more pointless when Ross (David Schwimmer) and Rachel just ended up together at the end anyway.

As for Chandler and Monica, seeing them settling into married life in the suburbs and preparing to be parents was the logical way to wrap things up for them. Still, it didn't mean that it was all that particularly exciting to watch. The fact of the matter is that Chandler being unlucky in love was always kind of the point of his character, and although he deserved a happily ever after, his character had lost his edge by that point. A notable outlier was Season 8's "The One Where Chandler Takes A Bath," which saw a rare Chandler-centric subplot that involved Monica but wasn't entirely about their relationship. Instead, the episode focuses on Chandler's newfound love of solo bubble baths, though he doesn't how to prepare one as well as Monica can. It was great to have one last example of such an episode before the final curtain fell on the series.

It took Matthew Perry zero time to find Chandler's voice. While it can be argued that most sitcom characters — the overall "Friends" ensemble included — usually don't come into their own until the second or third season, Chandler felt like a fully formed, well-polished character almost right from the start. And nowhere was this more evident than in Season 1's "The One with the Blackout."

The seventh episode of the debut season of "Friends," "The One with the Blackout" was the first true Chandler showcase. Chandler was locked in a bank lobby with real-life Victoria's Secret model Jill Goodacre, playing herself. The choice to have the audience hear Chandler's self-doubting inner monologue throughout the encounter could've come across as lame and gimmicky, but Perry's performance sells it, and it's hard to imagine the episode without it. Not having the safety net of his regular castmates, Perry proved here that he can easily carry scenes on his own — and we totally buy that Chandler actually has a shot with a beautiful lingerie model by the end of it. Of course, he fails to close the deal and lets the woman go with only a kiss on the cheek to show for it. He is still Chandler, after all.

Over the 236 episodes of "Friends," pretty much every possible combination of characters gets at least a couple of memorable scenes and subplots together. Still, some didn't get paired as often as others — including Rachel and Chandler, who get very little substantive screen time with only the two of them. And that's too bad, as Matthew Perry and Jennifer Aniston proved their chemistry was as good as almost any other set of actors on the show in episodes like "The One with All the Cheesecakes."

The episode itself might not be a five-star-earner, but the moment where Chandler and Rachel are on all fours eating cheesecake off the floor is as indelible a "Friends" moment as any. Beyond being a hilariously goofy visual, it also showcases the palpable platonic intimacy between the two that rarely got the opportunity to shine through. Aniston is often underrated as a comedic performer, and getting to have Perry as a scene partner — especially for such a silly set piece — was a great showcase for her talents. It's just an excellent example of how Chandler brought out the comedic best in his friends, just as Perry did for his co-stars.

Whereas "The One with the Blackout" establishes how funny Chandler could be, Season 2's "The One Where Heckles Dies" is where we get our first big taste of the melancholy that underpins Chandler's humor. Following the death of a neighbor of Chandler's (and Joey's, Rachel's, and Monica's as well), the gang was tasked with having to go through the deceased man's belongings and tidy things up. 

In the process, Chandler sees a lot more in Mr. Heckles (Larry Hankin) than he is comfortable with. This leads him to the conclusion that he might also die alone in a cluttered apartment with only strangers to come in and clean up after him. It showcases a whole other side to Chandler that we'd only caught brief glimpses of in the past and helped to make him a much more well-rounded character than just the sarcastic one-liner punchline guy. Perry's performance throughout is perfect, going from resignation to what he sees as his inevitable fate to realizing that he could take this as a cautionary tale in what not to do to end up like Mr. Heckles did.

Janice Goralnik (Maggie Wheeler) was one of the biggest recurring characters in the history of "Friends," starring in 19 episodes across all 10 seasons of the show (including a voice-only role during Season 6). Her on-again, off-again romance with Chandler was never the best or most healthy thing for either of them, but it led to both some of the funniest and also most tender moments for Mr. Bing. Honestly, a list of just the best Chandler-Janice episodes would represent some of the best episodes of the series, period.

That said, we went with "The One with All the Rugby" as the sort of stand-in on this list for the entire Chandler and Janice saga. It has some of the funniest and also saddest scenes between the pair, including Chandler going so far as to buy a plane ticket and even pretending to board a plane to Yemen all in an effort to ditch her once and for all. Given that this was a Season 4 episode and Janice would be back at least once for each of the subsequent six seasons, it clearly didn't stick. But this episode perfectly encapsulates the highs and lows that the complicated couple would experience, as well as how incredible the chemistry was between Wheeler and Perry — few scene partners throughout Perry's entire career brought out the best in him the way Wheeler did.

While we talked up how Chandler and Rachel got a rare subplot together in "The One with All the Cheesecakes," here we are spotlighting yet another episode where Matthew Perry and Jennifer Aniston got a lot of solo time with one another. However, in this case, the bulk of the heavy lifting was being done by Perry — and it also represents some of the best physical comedy he ever got to do on the show. If he wanted to have a career doing Jim Carrey-esque physical slapstick and rubber-faced comedy work, Perry's work in "The One with the Cuffs" proves that avenue was definitely available to him.

Chandler has a brief and very torrid love affair with Rachel's boss, Joanna (Alison La Placa), which leads to Chandler being handcuffed — and not completely dressed — in Joanna's office. Rachel eventually discovers him there, and to use a well-worn phrase, hilarity ensues. Aniston certainly does a lot of great work here, and once again, she and Perry are dynamite together. But this episode belongs to Perry, vamping and chewing the scenery in the best possible sense. Michael Richards as Kramer on "Seinfeld" might have been the king of physical comedy on primetime television in the '90s, but Perry was right there with him when the script called for it. 

Joey tolerates and forgives a lot from Chandler over the years, including being the other guy during Joey's aforementioned relationship with Kathy. But when it comes to Joey's family — in particular, his sisters — even the tightest and longest-running of friendships takes a clear backseat to him being in protective brother mode. And it leads to Joey slugging his best friend right in the face.

Initially, Joey couldn't be happier to find out that Chandler has started dating one of his sisters. Unfortunately, Chandler has no intention of actually having a romantic relationship with said sister. What happened between the two of them was nothing more than an alcohol-fueled one-night stand that Chandler barely remembers. In fact, he remembers so little of it that he doesn't even know which of Joey's sisters he had been intimate with. After trying in typical Chandler fashion — with some hilarious acting work by Matthew Perry in the process — to go along for the ride as he attempts to suss out which sister it was, he eventually has to confess to Joey that he has no idea which of Joey's sisters he had slept with. He also has to fess up that he never intended to have a future with her. The episode sees Perry doing some of the best nervous Chandler performing in the series, which is saying a lot. 

There are two different hourlong episodes of "Friends" that centered on the proposal and eventual marriage between Chandler and Monica. On first airing, they were presented as such, but are often separated into "Part 1" and "Part 2" when shown in reruns or on streaming services. But given that they were initially meant to be one-night events, we are counting "The One with the Proposal" (and "The One with Chandler and Monica's Wedding") as a single entry.

It's always tricky when a sitcom has two regulars suddenly enter a relationship a fair amount of the way into the show's run, but "Friends" deserves a lot of credit for its expert handling of Chandler and Monica's whirlwind romance. The episode where Chandler finally proposes to Monica is expectedly over the top — it's a proposal on a sitcom, after all — but is still fairly grounded and incredibly sweet. Perry and Cox were always great together, and Perry seemed to relish how much he was able to stretch his dramatic chops and show a more vulnerable side to Chandler throughout the character's journey of falling in love with Monica.

Sitcoms love to do wedding episodes. The ceremonies allow for all kinds of hilarious mishaps, they're an excuse to bring back plenty of recurring characters and guest stars, and there's the opportunity for drama as a result of cold feet, last-second jitters, or heartbreak on behalf of another character who wants to switch places with one of the people on the altar. Of course, there's no topping the botched wedding between Ross and Emily (Helen Baxendale) — which, ironically enough, is where Chandler and Monica first hooked up — but most of those boxes are still checked in the best ways for the wedding of Chandler and Monica.

It's debatable how interesting Chandler remains once he's actually married to Monica and becomes a husband in a happy, stable relationship for the show's last few seasons. But the wedding episode sees Chandler firing on all cylinders as a character, hitting both comedic and dramatic heights that represent some of Matthew Perry's best work — on "Friends" or otherwise. Wedding episodes have been done to death, and this one only barely has enough unique angles to stand out among that long sitcom tradition, but it's still a magical moment for fans of the show and of Chandler — and Perry — in particular. His saying "I do" to Monica will surely be a centerpiece of any clip package tribute to the actor's career.