Chandler Bing's Best Episode From Each Season Of Friends, Ranked

When "Friends" premiered in the fall of 1994, it marked both the beginning and the end of a pop culture era. The sitcom, centered around six twenty-somethings hanging out in New York City, was a departure from the family and workplace comedies that had come before it. But it was also a multi-cam traditional sitcom, shot in front of a live studio audience, with a laugh track to underscore the physical gags and one-liners. Maybe that's why "Friends" was so broadly appealing. It was fresh yet familiar, edgy yet wholesome, archetypical and not. 

More essential to the show's success than even the iconic settings of Monica's apartment and the Central Perk Cafe were the characters. Fans could describe them in one-dimensional terms. Ross (David Schwimmer) is the nerd. Phoebe (Lisa Kudrow) is the kook. Joey (Matt LeBlanc) is the himbo. Rachel (Jennifer Anniston) is prissy. Monica (Courteney Cox) is neurotic. Chandler, however, is harder to quantify. He's sarcastic, yes, but the late Matthew Perry created a character that's extremely specific and unique in his quirks, yet still extremely relatable. Though he doesn't get quite as many of the series' major storylines — at least not until his secret romance with Monica — Chandler is arguably the funniest member of the cast and the emotionally vulnerable core of the friend group. Clip reels might hone in on Chandler's most meme-able moments and catchphrases, but Perry's range lent depth and interest to the character's journey that can only be appreciated by a rewatch. These are Chandler Bing's standout episodes in each of the series' 10 seasons, ranked according to IMDb. 

Monica and Chandler's marriage is arguably one of the healthiest that's ever been portrayed on a sitcom, and Season 9, Episode 22, "The One With the Donor," is proof. They've been trying to conceive for a year, to no avail. A visit to a fertility clinic in the previous episode revealed that, though they're perfect for each other in every other way, they aren't reproductively compatible. Since Monica wants to carry a child, surrogacy isn't an option, which means they're in the market for a sperm donor. Chandler isn't just willing to raise a baby that doesn't have his DNA, he initiates the process by inviting over his hunky co-worker, Zach (John Stamos). Again, there's an undercurrent of what feels like homophobic humor (which is a criticism that's been leveled against the show), but isn't; that Chandler thinks Zach is so "sperm-tastic" means he's commendably secure in his masculinity. 

Over the course of a too-invasive dinner, Chandler and Monica grill Zach about his family's physical and mental health history. Chandler concludes that, even if his little swimmers could do the job, Zach would be the way to go. But Monica — though she's taken by Zach's tidiness — sees things differently, and decides she'd rather adopt. The couple is excited at the prospect of having a child sooner rather than later, and Chandler looks forward to messing it up in their own specific way. 

Season 7, Episode 5, "The One With the Engagement Picture," is pretty straightforward and one-note, but that doesn't make it any less funny. The new character detail we learn about Chandler Bing in this episode makes for the kind of visual gag that the viewer can't help but laugh out loud at, and anyone who's ever been displeased with what the camera captures can feel for him. 

When Monica's parents want a photograph of the happy couple for the wedding announcement they're going to run in the newspaper, Chandler warns his fiancée that he's incapable of taking a good picture. Phoebe inspects their candid vacation photos and confirms it. Hearing about Chandler's unphotogenic-ness is one thing, seeing it in action is another. Their first sitting — in front of a watercolor blue background at a mall-like studio — is a disaster. Chandler simply cannot smile naturally on cue. Each attempt becomes a more painfully uncomfortable and borderline inhuman grimace. 

Joey, who has experience posing for headshots, tries to give him some advice. He tells Chandler to look down for three seconds, then look up at the last moment to make his expression seem less forced. But their second appointment goes no better, and in the end, Monica's parents publish a toothy photo of her and Joey instead. 

Whether Chandler is properly manly enough is a running thread throughout the tapestry that is "Friends." There's a whole episode (Season 1, Episode 8, "The One Where Nana Dies Twice) devoted to the idea that everyone thinks Chandler could plausibly be gay. But whatever Chandler's "quality" is, he gets more in touch with it as the show progresses, and what could read like borderline offensive jokes in early seasons become more layered and nuanced story beats in later ones. Season 8, Episode 13, "The One Where Chandler Takes a Bath," is a case in point. 

At the start, a newly married Chandler is hung up on hooking up with his wife on the balcony. But Monica wants to relax with a soak in the tub. Chandler doesn't get it because he's not a bath person, and he emphasizes that baths are just "stewing in your own filth." Monica makes it her mission to convince him otherwise. She draws him a bath with bubbles, essential oils, rainbow votive candles, and Enya playing in the background. And, to "butch it up" a bit, she buys him a plastic boat. Chandler's instantly won over ... particularly by the brand new and pleasurable sensation of the effervescent bath salts. But he's bummed out to discover that fixing the perfectly relaxing bath is harder than it looks. 

The shenanigans conclude when all six friends congregate in Monica and Chandler's bathroom, with him still naked in the tub. Refreshingly, Chandler is neither embarrassed by his love of flowery-smelling baths or his little plastic boat. 

Most long-running shows get a little hard-pressed for good ideas as they wind down. "Friends" fell into that trap, too, particularly with the messy love lives of Ross, Rachel, and Joey. One of the bright spots in the final season, however, was Monica and Chandler's efforts to adopt a baby. In Season 10, Episode 9, "The One With the Birth Mother," the hopeful parents travel to Ohio to interview a woman who could be the answer to their prayers. Erica (Anna Faris) starts asking them questions. Chandler is as witty and Monica is as confident as ever, but it quickly becomes clear she has them confused with another couple. She thinks that Monica's a reverend and that Chandler's a doctor. He's about to correct Erica when Monica stops him in his tracks and starts (mis)quoting the Bible. Erica chooses them to be her baby's parents, but Chandler feels conflicted about their dishonesty. 

In this episode, Chandler is as clever and quippy as always but also deeply earnest. Though his wife is willing to lie for the chance to raise Erica's child, Chandler is willing to risk the adoption to clear his conscience. When he confesses, Erica rescinds the offer. But Chandler follows her into the hallway and gives a monologue about Monica that would put all other husbands to shame. He tells Erica that he hates to admit it, but she's always right, and that it kills him he can't give her the baby she wants so badly. Sensing how devoted they are to each other, Erica reverses her decision and makes the Bings' dream come true.

Until Season 4, Chandler's love life had been played mostly for comedic effect. We're only able to take him seriously as a love interest for Monica later on because he's so charismatic in the arc involving Joey's girlfriend, Kathy (Paget Brewster). By Season 4, Episode 7, "The One Where Chandler Crosses the Line," it's already been well established that Chandler has a massive crush on Kathy, whom Joey met in acting class. Joey likes Kathy, but he isn't ready to be exclusive, as he makes clear to his roommate when he schedules two dinner dates with two different women on the same night. As it happens, he can't make it to his dinner with Kathy, so he asks his best bud to step in. 

And step in he does. Alone in the apartment together, Chandler and Kathy's chemistry becomes palpable. She offers to give him a haircut, which only makes the situation more sexually charged, culminating in a goodbye kiss. Chandler stays loyal(ish) to Joey and tells Kathy they should forget about the kiss and ignore their feelings, even if it means they're both unhappy, but Kathy's not sure she can. The episode is plenty laugh-worthy, even when Joey finds out, and that humor carries over into the next episode, "The One With Chandler in a Box." It's the genuineness of Chandler's affection for Kathy and his struggle to do right by his friend that give "The One Where Chandler Crosses the Line" more weight. Though the relationship with Kathy doesn't last, it shows the audience what a good catch Chandler Bing is.

Season 1, Episode 7, "The One With the Blackout," is the kind of tried-and-true sitcom premise that allows for some otherwise unlikely scenarios to occur. When all of Manhattan and some of the surrounding boroughs go dark, the friends — save for Chandler — are stuck in a candlelit apartment. Ross tries to work up the courage to ask Rachel out ... which he can't do before suave, cat-owning Italian, Paolo (Cosimo Fusco), makes her acquaintance. Chandler is trapped before the automatic glass doors of an ATM vestibule (or is it an atrium) with Victoria's Secret model Jill Goodacre. 

The set-up is a showcase for Chandler's particular brand of awkward, self-deprecating comedy. He spends most of his time alone with the intimidatingly gorgeous woman talking to himself in his head. When he's forced to interact with her after she offers him gum, he repeatedly embarrasses himself, first by replying that "gum would be perfection," and then by rejecting her offer because the gum isn't sugar-free. He accidentally spits out the wad trying to blow a bubble to impress her, then puts the wrong gum back in his mouth and has to be rescued by the model when he chokes in disgust. The encounter goes so badly, that it endears Jill to Chandler, which is exactly how the audience feels about him as well. When the episode ends, both the viewer and Chandler get the sense that, had he gone for it, she would've been open to his advances. But all he'll ever have is a good story ... and maybe the security footage. 

Chandler and Joey get into yet another best friend's squabble in Season 3, Episode 2, "The One Where No One's Ready." Ross has to attend a paleontology fundraiser at his museum, and he's invited Rachel and the rest of the gang to attend. But their table's right in front, and it'll look bad if he arrives late. To his utter dismay, his friends are all lounging around in their sweats and undergarments with exactly the runtime of an episode left until it's time to leave. Rachel can't decide what to wear. Monica is hung up on calling back her ex-boyfriend, Richard. Phoebe gets hummus on her dress. And Chandler and Joey are fighting over a chair. 

"The One Where No One's Ready" depicts Chandler as stubborn, childish, and petty ... which are definitely elements of his personality. When he returns from the bathroom, Joey has taken his seat. Chandler doesn't believe that leaving to pee means the seat is now ready to be taken by someone else and he refuses to accept Joey's counterargument. For once though, Joey gets the upper hand. When he heads to his apartment to change into his tux, he takes the chair cushion with him. Then, when he discovers that Chandler hid all of his underwear as an act of revenge, he does "the opposite" and dons all of Chandler's clothes, sans boxers or briefs. Joey has the more visually memorable outfit, but Chandler's exasperation at not getting his way is what makes the whole chair bit work. It happens again in the post-credits scene in which Chandler loses his seat at the museum fundraiser. 

It is a foregone conclusion that Chandler and Monica are going to be engaged by the end of this two-part episode — which serves as the finale of Season 6. What happens in between, however, is where all the comedy and drama come in. Chandler has made reservations at Monica's favorite restaurant, where he intends to pop the question over a bottle of her favorite champagne. Coincidentally, Richard (Tom Selleck) — Monica's hyper-masculine and mature ex — brought a date to this particular culinary establishment, too. The self-aware potential husband-to-be introduces himself by saying, "I'm Chandler. I make jokes when I'm uncomfortable." His proposal thwarted, Chandler tries to preserve the surprise by suddenly claiming to be anti-marriage, just as Richard declares he's still in love with Monica. 

Chandler's ruse gives Matthew Perry a chance to play the character as a "complex fellow who's unlikely to take a wife," as Joey puts it. Once the roommates determine that Richard's a real obstacle, the race is on to present Monica with the ring. But first, Chandler shows up at Richard's apartment where he correctly deduces his girlfriend has been. In confronting Richard, he gets a practice run at his speech. Rather than fight him for Monica, Richard encourages Chandler to go get her. When he gets back to the apartment complex, Joey tells him she left upset that they want different things. But the joke's on him ... if you can call an enormously romantic gesture a joke. In the confusion of Chandler's botched plan, Monica got the opportunity to turn the tables and surprise her best friend in one of the sweetest engagement episodes in TV history. 

Season 2, Episode 14, "The One With the Prom Video," is often cited as one of the best episodes of "Friends." It's most famous for Ross and Rachel's kiss after Rachel learns Ross once planned to accompany her to the prom when her date failed to show, and for being the installment that introduced the concept of "the lobster." But the subplot features a classic Chandler and Joey conundrum. 

Now that Joey's gainfully employed, he repays Chandler the money he owes him and throws in an engraved gold bracelet for good measure. It's painfully obvious from the moment Chandler lays eyes on the bauble that it's not his style. He tries to stash it in a drawer, claiming he'll save it for special occasions, but Joey insists he sport it on the regular. The rest of the friends have fun making snarky comments at Chandler's expense for once. Ross says it's not too flashy for a Goodfella. But Joey happens to walk in just as Chandler's ranting (in character as Mr. T) about how much he hates the bracelet, which he calls a woman repeller. 

Joey's understandably hurt, so Chandler agrees to keep wearing it ... except he's lost it en route to their apartment. He spends hundreds of dollars to replace it, only for the original to be found shortly thereafter at the coffee shop. In possession of two bracelets that he doesn't want, Chandler improvises on the spot and gives one to his best friend, so they can be "bracelet buddies." The ordeal shows Chandler — hilariously — at his most flummoxed and well-meaning.

Ross and Rachel may have been the will-they-won't-they that fueled "Friends" in its first few seasons, but Monica and Chandler's tryst-turned-true love became the show's more satisfying romance. There are myriad great Chandler and Monica moments, starting with the revelation that Chandler's hiding under her sheets in "The One With Ross' Wedding." Who knows and who doesn't know about their relationship complicates things from the Season 4 finale onward, and everything comes to a head in Season 5, Episode 14, "The One Where Everybody Finds Out." 

Leading into the episode, Joey and Rachel are already privy to Monica and Chandler's secret. Phoebe catches on when she sees Chandler take off Monica's blouse from Ugly Naked Guy's (Jon Haugen) apartment, which Ross is in a bidding war to rent. But rather than confront their friends, Phoebe and Rachel hatch a plan to coerce Monica and Chandler into coming clean. A sultry-voiced and sexually forward Phoebe attempts to seduce Chandler, who flirts back with competitive coaching from a completely unthreatened Monica. 

At this point in the series' run, Chandler is a legitimate leading man — on the show and in real life. But for this episode, he's back to being an inept lover, even more so than he was at the show's start. Team Chandler and Monica "lose" after one cringe-worthy kiss when he shouts out — for the first time — that he's in love with his long-time friend.