The Ten Best FRIENDS Episodes of Season Five

Welcome to Sitcom Tuesday and the continuation of our coverage on the best of Friends (1994-2004, NBC), one of the most popular American television comedies of the past 30 years. The entire series has been released on DVD, Blu-ray, and is streamable on several online platforms. [For these posts, I studied the uncut episodes as they appeared on the original DVDs.]

Friends stars JENNIFER ANISTON as Rachel Green, COURTENEY COX as Monica Geller, LISA KUDROW as Phoebe Buffay, MATT LeBLANC as Joey Tribbiani, MATTHEW PERRY as Chandler Bing, and DAVID SCHWIMMER as Ross Geller.

Season Five is, like Four, among the years I most commonly see cited as the series’ best. Frankly, it’s also one of the easiest to enjoy — and for the most part, I do, considering it in league with its three predecessors as a contender for the show’s finest. But, as with every season since, say, the 1996 calendar year, the characterizations are getting unfavorably broader — Rachel is more manic, Monica is more obsessive, Phoebe is more cutting, Joey is more ignorant, and Ross is more bumbling. (Interestingly, the exception is Chandler, who’s getting less sarcastic, and more emotionally well-rounded.) And yet… for the bulk of Season Five, the scripts motivate this heightened comedic posturing with enough traces of humanity to keep us from divesting. And, indeed, earned laughs serve as a justifying agent for moments where the character work might otherwise seem strained. That is, the heightening has extended to the comedy, and for the first three-quarters of the season, there are no consequences of a significant nature. On the contrary, Five offers classic, memorable installments — many of which, unsurprisingly, contend with the blossoming (secret) romance of Monica/Chandler, which the writers had allegedly been discussing since Season Two. If you’ll remember, I opined that the addition of another central couple within the ensemble was necessary given the writers’ refusal to re-pair Ross and Rachel, who were established as the series’ emotional foundation and drove a lot of the heavier stories (read: Sweeps episodes) in the first four seasons. Disinterested in writing for them again as a duo, perhaps rightly recognizing that conflict is inherently more fun, the show then hungered for a new couple through which it could channel its rom-com sensibilities… Accordingly, Monica/Chandler reinvigorates the show as intended, taking over for Ross/Rachel and supplying the scripts with an emotional bedrock that had long been missing. This return to a storytelling that reinforces Friends‘ premise-based romance, coupled with the novelty of a new love, is why Five is one of the easiest years to enjoy. That would stand regardless of quality.

Fortunately, the year’s quality does warrant praise — particularly for the treatment of Monica/Chandler, which isn’t teased (or teased out) in the same way Ross/Rachel were, providing an emotional contrast: stability. Oh, sure, the creators insist that Monica/Chandler was intended to be “temporary” — a shot of adrenaline, not unlike last year’s apartment swap or Phoebe’s pregnancy arc — but the nature of Ross/Rachel in this period belies the need for something of equal permanence, and whether or not the show began by hedging its bets, I think it’s already clear by the year’s third outing (the 100th) that this is, in fact, going to be a serious development. From there, the reveal of their romance is plotted out like textbook Friends — timed for the weeks where ratings matter most: Joey discovers in November, Rachel in the first episode back in January, and then Phoebe (and Ross) in February. It’s a little too perfect, but it is well-built, designed to maintain the tension and excitement surrounding a hush-hush affair of growing depth, indicating a terrific understanding of what the show needs at this point in its existence… Yet aside from benefiting the show in a wider sense, Monica/Chandler is also great for their characterizations: a blending of their established emotional arcs — her pilot-born quest for romantic fulfillment (quickly shown to be a “picture perfect” idea of a husband and family), for which she rejected Richard but which she now has to reject, in part, to be with Chandler, and his long-term struggle with commitment in the form of emotional vulnerability (which was developed within the show’s first two seasons and then came to certain crisis points with Janice and Kathy), when he opted to commit, and then actually grew. In both cases, Chandler and Monica (no longer starved for stories — she’s in a permanent relationship now) grow simply by being together. And more than anything, that’s a reason to not only root for their pairing — we do so instinctively, because we’re invested in them both — but to laud the show for it.

Monica/Chandler also takes the heat off Ross/Rachel, which is still “meant to be”… just not for a while. We’ve discussed this ad nauseam before, but here, I’ll reiterate that I agree the show works best, structurally and episodically, when it employs a design that doesn’t prioritize Ross/Rachel at the expense of the others. In Four, the prolonging of their reunion didn’t preclude them from anchoring key moments (like Sweeps) — even if that meant dedicating the back half of the year to setting up the preordained London trip and the Ross/Rachel yarn that would power the year’s ballyhooed finale. (Three did the same thing, but on a smaller scale, and when Four’s premiere dashed the possibility of their re-coupling, it showed us, believably, why: neither had grown enough since their break-up.) So, when the fourth year ended, much like the third, with a cliffhanger centered around Ross/Rachel, their reconciliation seemed again a possibility. But with hindsight, we know that it never was, especially now that Monica/Chandler could fill the show’s weekly romance quota. Thus, Five’s first few episodes have two goals. One, ending the Emily arc — ostensibly because Baxendale was pregnant. (But really, how much longer could this ill-defined complication have stuck around, anyway?) And two, explaining why Ross/Rachel still aren’t getting back together. The show doesn’t do either well — but Emily’s demise matches how the arc was established, so I’m not going to complain about the cessation of a storyline that never worked outside the cliffhanger. As for Ross and Rachel, motivating the latter’s dead-in-its-tracks pursuit of Ross is harder, given the prior finale, but the show removes the football quickly (unlike Six). And even though we don’t truly understand why they’re not getting together — for we know his marriage is going to be short-lived (as the show’s premise isn’t changing) — both characters behaved sans motivation/growth within the arc, so we’re less invested in their reconciliation at this moment; they shouldn’t be together now, honestly… and for the first time ever, the show doesn’t need them to be either.

So, with Ross/Rachel settled early, the rest of the year can turn itself elsewhere — it doesn’t even need the pair for Sweeps. In fact, with few exceptions (like the year’s finale — discussed below), Ross/Rachel is indefinitely paused… and it’ll stay that way for much of Seasons Six and Seven, perhaps to those years’ detriments. Here though, because we have a fresh and novel coupling in Monica/Chandler, Ross/Rachel simply can afford to become a secondary concern. (And the handling of the Emily story makes us glad that we’re “on a break” from them… for a little while, anyway; remember, they’re still thesis-deigned.) Instead, Five goes back to their personal arcs. Rachel is allowed to progress in her career (a symbol of her individual growth) by moving to Ralph Lauren, after a misbegotten arc with Danny, a temporary love interest that serves her characterization no better than Joshua’s did. (The less said about it, the better…) And Ross, after losing his wife, his home, and his job within a month, finds his persona at a “pivot” (pun intended) point; he’s always been somewhat of a lovable loser — from the pilot, when he had to deal with the dissolution of his first marriage — but he often was a victim of circumstance. Now, the show amps up Ross’ aggression (it starts as part of a motivated storyline — “anger issues” — yet persists for the remainder of the series) and makes him more of an active participant in his own conflicts. He’s wilder, goofier, and more episodically driven (that is, he has comedic ambitions that so obviously serve a functional weekly purpose) than ever before. In other words, he’s broader. This change is sometimes a bitter pill to swallow, but Schwimmer relishes the enhanced opportunities that come from this broadening — he’s an expert at physical comedy — and for the most part, his efforts justify the evolution.

I’m not sure if the same can be said for Phoebe, who also undergoes a radical personality change — a fact that gives credence to my belief that Monica/Chandler’s pairing carries some responsibility for the concurrent character alterations. (More on that below…) First though, I posited last time that the pregnancy storyline, which concludes here in the series’ 100th outing, was perhaps the apex of Phoebe’s pursuit of family, for she gave one to her new one. But, that wasn’t the end of her arc, so now she, too, has to pivot. After getting a taste of a family, she has to go out and make one for herself. That’s her goal for the rest of the series. However, Friends is terrible about tracking this — and doesn’t give her tangible growth for years. Even in Five, before this lack of development is as crushingly obvious, Phoebe’s personal arc is not as satisfying as we’d anticipate — she meets her father in a single middling entry that’s barely addressed again, and then has her first multi-episode romance (actually a big deal) with Gary the Cop (Michael Rapaport). This relationship starts out interestingly but ends abruptly with a strange, cop-out ending… and without any visible ramifications for her in the weeks that follow. (Frankly, the show doesn’t offer any emotional substance to Phoebe until her arc is finally allowed to progress in Season Nine. We’ll be following this notion of non-progression, for all the regulars, later; stay tuned…) But, hey, at least Phoebe has an arc in Season Five; Joey, on the other hand, doesn’t get much. He basically plays the wandering minstrel, fulfilling episodic story by carrying a lot of the Monica/Chandler “secret relationship” load, while his characterization broadens and he becomes an easier source of quick humor — usually in relation to others.

Having Joey act in response to Monica/Chandler is telling, because it presages a side effect of this coupling (which isn’t fully obvious until Season Six): that Joey and Chandler are spending far less one-on-one time together. This, as we’ll explore in future weeks, is a shame… But that’s not the only change we’ll be observing, for the existence of this romance has additional consequences — like the eviction of Rachel from Monica’s, a development that further cultivates other relationships besides Rachel/Monica and Joey/Chandler, which have thus far been the core friendshipsWe’re talking now of Rachel/Phoebe (who become roommates), Ross/Joey (who hang out more often), and Rachel/Joey (which starts when she moves in with him, and then turns into something different several years later). All of these new combos provoke already developing character trends. For instance, when Joey is with Ross, he becomes dumber in contrast; when Ross is with Joey, he becomes hyper in sympathy; when Rachel is with Joey, she becomes sillier for compatibility; and when Phoebe is with Rachel, she takes on a harder edge as a means of attitudinal delineation. To that last point, the signs of Phoebe’s more-quick-to-anger persona are the most evident in Five, originating at the end of her pregnancy (with the mood swings) and popping up situationally (like when she turns into “Street Phoebe”), before it becomes permanent in Six. Unlike with Ross, however, I’m more bothered by this pivot’s severity… Also, we can already see changes for Monica and Chandler. While he becomes less extreme and more modulated — a sign of his growth, which seems like it would bring a reduction in humor, but thanks to the writing, actually just makes his comedy more nuanced — Monica’s shrilly obsessive need for order goes into overdrive, as the series hopes to derive conflict for Monica/Chandler within their relationship (so they don’t become “boring,” which was the fear with Ross/Rachel). It’s glaring throughout Five, and will become more so in Six, when it’s harder to invest in her truth, even if we still support their relationship…

As noted above though, the characterizations in Five are generally not bothersome — they’re merely heightened for comedic opportunity (as opposed to heavy-handed story goals), and while Joey and Phoebe don’t have their emotional arcs well-realized, there’s still a feeling of forward momentum, even for the otherwise paused Ross/Rachel (because they’ve got individual material), as Monica/Chandler’s growth symbolizes a season of character value… until, well, the last quarter of the year, when the writing begins a more obvious resettling, setting the stage for bigger changes at the top of Six… Now, there was a slight staff reorganization starting with the year’s 19th— promotions for writers who were sticking around for Season Six, which would otherwise be without several key scribes. But there’s no other connected external or internal excuse as for why, starting with the year’s 20th, the stories become forced and the players go broader (Monica and Phoebe both get pretty mean, Joey loses many IQ points). They simply do… And I can’t sugarcoat anything: these last few episodes are bad, with one of the weakest finales of the entire run (rivaled only by the Barbados trip), and it’s the main reason that my fondness for Five is limited. I only have two positive things to say about the year’s last (two-part) episode, set in Vegas. One, at least Five doesn’t spend half the year trying to explain it, and only uses the excursion prior to the (double-length) finale for set-up, thus keeping the stink of Vegas off the rest of the season. Two, I like that there’s some reconciliation of Chandler’s reduced fear of commitment in his story with Monica, indicating how much he’s already grown… Unfortunately, it comes in a labored teleplay filled with juvenile characterizations that insult the intelligences of Ross and Rachel, showcase Phoebe at her ragey, umotivated worst, and bring Joey to the HEIGHT of his stupidity (unmatched until the final season, when this kind of audacious laugh-seeking imbecility becomes less situational than fundamental).

What’s more: the whole thing, a seeming “on location” (but not really on location) attempt at keeping up with last year’s London brouhaha, is contrived only for the final cliffhanger, where Monica and Chandler stop short of getting married — a development worthy of an eye-roll, for the script has to toil to get there — when they see Ross and Rachel stumbling out of the chapel instead. Egads, folks. This represents the worst example of the show trotting out Ross/Rachel to deliver a big Sweeps moment, trying to maintain the audience’s investment in their pairing even if the next season has no intentions of actually putting them together, because not only is it unmotivated by the text, but their relationship hasn’t been the focus of the season since the start. A Ross/Rachel cliffhanger simply isn’t earned. In terms of storytelling, this is bad for several reasons — irrespective of how it’s handled in Six. (Spoiler alert: not well.) It’s a gimmick that arises situationally from what’s been forced into the weekly plot. Shock value all the way. Beyond feeling ill-motivated though, it’s also extraneous — Monica and Chandler have become the new provider of Friends‘ romantic stakes, and even though Ross/Rachel have a “birthright” claim on this power, including them as the focus now feels regressive… especially when that so clearly wasn’t the intent of the fifth season. Also, it’s yet another example of story (or here, a commercialistic cliffhanger) being prioritized over the regulars… And yes, all of my commentary is colored by knowledge of what’s to come, but even if we ignored the aftermath, the lack of motivation is galling and isn’t consistent with the first three-quarters of Five, which is a funny season that moves the characters forward (generally), finds a way to prolong Ross/Rachel without leaving the audience wanting, and boasts a veritably exciting, smart, and character-geared new relationship. It’s basically, then, a strong year… with a bad last stretch that reveals more of what’s to come… But that’s for next week. In the meantime, I have picked ten episodes that I think exemplify Five’s finest. (They are in AIRING ORDER.)

Regular writers this year include: Marta Kauffman (Dream On, The Powers That Be, Grace And Frankie) & David Crane (Dream On, The Powers That Be, Episodes), Adam Chase (Veronica’s Closet, The Weber Show, Better With You), Michael Curtis (Dream On, Veronica’s Closet, Phil Of The Future), Gregory S. Malins (Veronica’s Closet, Will & Grace, How I Met Your Mother), Alexa Junge (Veronica’s Closet, The West Wing, Grace And Frankie), Wil Calhoun (Caroline In The City, What I Like About You, Whitney), Seth Kurland (Mad About You, 8 Simple Rules, Melissa & Joey), Shana Goldberg-Meehan (Mad About You, Joey, Better With You), Scott Silveri (Mad About You, Joey, Speechless), Ted Cohen (Mr. Rhodes, Work It, Veep) & Andrew Reich (Mr. Rhodes, Romantically Challenged, Work It), Gigi McCreery & Perry Rein (Becker, Yes Dear, Wizards Of Waverly Place), and Alicia Sky Varinaitis (Kristin, Nikki, The Buzz On Maggie).


01) Episode 99: “The One With All The Kissing” (Aired: 10/01/98)

Monica and Chandler kiss in front of the group; Rachel wants to tell Ross she loves him.

Written by Wil Calhoun | Directed by Gary Halvorson

This outing is popular, I think, because of the one-joke story with Chandler having to kiss all the women in the regular cast to cover up his accidental slip with Monica — an idea that caters to some of those self-indulgent fan-fictiony desires to explore all the different couple possibilities within the ensemble… Needless to say, it’s an emotional gimmick that’s tenuously character-driven. Also, I think the installment also claims a few incredibly broad characterizations — some of which are jarring because it’s the first real indication of Five’s contribution to the annual uptick in heightening. Most troubling is Rachel, whose feelings for Ross drive the A-story (just like they did in the prior finale), but must be capped off by the end of the half-hour, for the show isn’t going to get them back together. (The tease was just for the cliffhanger.) Indeed, it’s a contrivance — Aniston tries her hardest to pull it off, but the over-the-top comedic strokes don’t quite work; we’re just glad it’s over. Meanwhile, it is actually the Monica/Chandler material that earns the entry its spot — not because of the gag, but because of the sense of excitement at their new pairing, which is fresh and fun and contrasts against Ross/Rachel, who have too much baggage (narratively and textually, from the show’s strained usage of them these past two years). I don’t think there’s any other offering this year that so ably illustrates what a breath of fresh air Monica and Chandler are for Season Five, and that’s why I include it here.

02) Episode 100: “The One Hundredth” [a.k.a. “The One With The Triplets”] (Aired: 10/08/98)

Phoebe wants to keep one of the triplets; Monica threatens to date someone else; Joey has kidney stones.

Written by David Crane & Marta Kauffman | Directed by Kevin S. Bright

Because this is the 100th episode, it gets to be one of the rare IMPORTANT OUTINGS that wasn’t groomed for a Sweeps broadcast, and to its credit, while it does contend with a big event (that seems befitting of a series that is mindful of its commercial interests — it wouldn’t dare let the 100th show go by with a “normal” excursion), the weight of the story doesn’t crush the characters. This is mostly because the Phoebe arc, in which she births her brother’s triplets, has been so perfect for her character, given the objective that we saw develop for her in Seasons Two and Three. Thus, the story feels justified, and thanks to a funny script (the doctor who loves Fonzie is a unique hoot — a genuinely original comedic idea) that also contributes some earned pathos (Phoebe having a hard time giving up the babies is great), it all works. Also, as discussed above, the entry’s use of Monica and Chandler contradicts the creators’ claims of being unsure about how long Monica/Chandler would last, for by this time, the show dedicates a whole story to making them become more serious, and there’s therefore a “pivot” (pun intended) in how the series is using them — not just for laughs or temporary excitement, but for emotional, character-rooted substance: the same thing that Ross/Rachel previously provided…

03) Episode 102: “The One With The Kips” (Aired: 10/29/98)

Monica and Chandler argue on a weekend away; Ross tells Rachel what Emily requested.

Written by Scott Silveri | Directed by Dana DeValley Piazza

In accordance with the year’s broadening, everything is bigger — including the ideas that don’t work. Here’s what doesn’t work about this entry: the Ross/Rachel A-story that has to continue the Emily arc (without her physically being there) and does so with some forced drama that we know isn’t going to have any bearing on the characters. Obviously, the show is not going to uproot its structural premise and keep Ross from seeing Rachel anymore. This whole drama exists for the purpose of episodic narrative (and, okay, to give some weight to the inevitable end of the Emily storyline — which I believe was doomed for a short life anyway, based on the cliffhanger and the series’ rom-com “Ross and Rachel are meant to be together” posturing, but heck, it was ill-conceived and gimmick-led from the jump). The comedy supports it somewhat though, mostly in the emerging backstory about Chandler’s former roommate “Kip,” which holds inherent fascination for the history it suggests about the group… Nevertheless, what really makes this episode worthwhile is the Monica/Chandler subplot, for it’s not only the vehicle that (following the intensification of their dynamic in the 100th) leads Joey to discovering the news — just in time for November Sweeps — it’s also the first indication that their respective personalities (not situational circumstances) can provide conflict in a real relationship. In this regard, it’s an essential narrative usage of these characters. At the same time, it also indicates how Monica has to broaden in order to play this kind of material opposite Chandler — reflecting the other side of the coin honestly, and, for now, humorously.

04) Episode 105: “The One With All The Thanksgivings” [a.k.a. “The One With The Thanksgiving Flashbacks”] (Aired: 11/19/98)

The group recalls their worst Thanksgivings ever — including two with relevance for Monica and Chandler.

Written by Gregory S. Malins | Directed by Kevin S. Bright

Flashbacks on any series — I don’t care what it is — are a gimmick, but they’re a great structural hook for a story-heavy show that wants to maintain some notion of character relevance, for theoretically, these flashbacks tell us something about who they are (or rather, who they used to be). More often than not, though, they’re a way to gin up episodic excitement, employ humor based on hindsight knowledge, and tell stories where the audience already has a vested emotional interest — little work needed. The job of these shows, then, is to justify that they exist for more than their gimmickry — either by actually being revelatory for character or by being hilarious. In this case, I’d argue that the two main flashbacks — featuring Ross, Rachel, Chandler, and Monica — prove their value via comedy. (The others are only driven by a single gag — Chandler’s gay dad, Phoebe’s absurdity, Joey ripping off Mr. Bean — and are collectively adequate.) As for how those two stack up regarding character, I think they supply a forced history with the sole goal of providing an emotional underpinning for Monica/Chandler, in the same way that Ross/Rachel have with the Prom Video (which is, incidentally, the last time we saw Fat Monica — but that was diegetic: it came from a tape, not a “memory”). The reveal of Monica initially liking Chandler and losing weight because of him feels a little too conveniently relayed — like it only exists to make a point about their current relationship. But at this moment, we like their relationship so much that the we’ll go along with it. And, in doing so, this is where I think Ross and Rachel (temporarily) pass their torch to Monica and Chandler — now the latter couple also has a history, and are, in rom-com lingo, “meant to be.”

05) Episode 106: “The One With Ross’s Sandwich” (Aired: 12/10/98)

Ross is enraged when a co-worker eats his sandwich; Joey covers for Monica and Chandler.

Written by Ted Cohen & Andrew Reich | Directed by Gary Halvorson

Another uneven offering, this installment is well-liked because of the comedy thrown at David Schwimmer, whose Ross (as discussed above) enters into a period of misfortune — losing his wife, his apartment, and in this entry, his job. This, as we’ll start to see over the next few years, shifts his characterization permanently, for as a means of giving this natural clown more chances to showcase his ability to handle some of the broader comedy with which others (like Cox) struggle, Ross becomes more of a mess than ever — desperate, manic, and at times, silly. It’s a comedic contrast to the brains that he also continues to exhibit (and which are reinforced by his career choice), but Schwimmer makes a lot of this new angle work (despite the broadening). A great example is this story, which takes the simple, amusing notion of someone eating Ross’ sandwich and uses it to push the character to his breaking point. Ross had been naturally quicker to anger so far this season — a function of his heightened playing, in general — and by calling it out, the show gets to have its cake and eat it, too, making for a seminal Ross showcase. That’s why this excursion is worth highlighting, for Ross’ stuff is fun enough to overcome a Joey storyline — where he continues to cover for Monica/Chandler — that doesn’t adequately earn its broadness. (The “cover” of Monica sleeping with Joey is another fan-fictiony “alternative couple” gag that affronts logic based on how everyone reacts, or doesn’t.)

06) Episode 108: “The One With All The Resolutions” (Aired: 01/07/99)

New Year’s resolutions prove difficult to keep for the group — especially Rachel, who learns a big secret.

Story by Brian Boyle | Teleplay by Suzie Villandry | Directed by Joe Regalbuto

The thematic cohesion of uniting every story under the umbrella of New Year’s resolutions helps both distract from the innate unevenness (the Phoebe/Joey material is obviously less emotionally interesting or comedically valiant than the others) and motivate what is otherwise a gaudy story turn: Rachel’s discovery of Monica and Chandler, which comes in another big show: the first entry of the new year, of course. As with several of the above, there’s a narrative convenience — Rachel is suddenly a gossip because the episode tells us she is, and even though it’s not a stretch based on her characterization, it does feel like something that only exists for the purpose of story… a way to frame her discovery of Monica/Chandler and still keep it a secret. Again, we leap because we want to (although we may NOT want to make these same kinds of leaps later, if the results don’t seem to be as worthwhile)… Meanwhile, the strength of this outing comes from Ross, whose resolution to do one new thing a day is general enough for the show to throw whatever it wants at him — and here, it’s more broad physical comedy, as Ross gets stuck in a date’s bathroom wearing a pair of tight leather pants that he can’t get back on his body. It’s an iconically hilarious bit — and Schwimmer, as usual, plays it to the hilt. More than anything, that’s what makes this outing such a winner. A near-classic.

07) Episode 111: “The One Where Everybody Finds Out” (Aired: 02/11/99)

Phoebe finds out about Monica and Chandler and schemes with Rachel and Joey to get them to confess.

Written by Alexa Junge | Directed by Michael Lembeck

My pick for the best episode of the fifth season, this popular outing would be a tough one to not consider among the series’ best, for the sheer density of laughs is amazing. This is one of those Friends installments that’s just chock-full of hilarious, rapid-fire character moments… which are all the more impressive given the fact that there’s a perfectly timed (for Sweeps) narrative objective, too — getting everyone else to find out about Monica/Chandler and essentially transitioning them from a clandestine liaison to a full-fledged relationship that, in every way, takes the romantic comedy spot currently vacated by Ross/Rachel. (The rom-com intentions are at play already — the “in love with Monica” reveal, which doesn’t seem like much of a reveal given how the year has heretofore built their commitment, is how the outing secures its necessary “heart.”) But, these story machinations are part of that romantic comedy aesthetic, which is also vital to every Friends script that wants to be a legitimate contender for the top spot. (Just think of “…The Prom Video” or “…No One’s Ready” and how they used the show’s romance.) And as a result, if the story idea still seems cumbersome even with the abundant — and I mean abundant — comedy, it would remain earned based on the particulars of this series and its always-encouraged aesthetic. Yes, Phoebe flirting with Chandler is yet another gimmicky “alternative couples” beat, but these two characters (and actors) are so funny and so seldom used together in story that it is riveting. Also, with so many memorable lines and bits, it’s easy to forget how well the entry sets up Ross moving in across the street — which yields a couple of choice gags (both Phoebe’s and Ross’ discovery of Monica/Chandler and Ross’ nude bonding with Ugly Naked Guy) and later proves narratively valuable in the years ahead. A gem.

08) Episode 112: “The One With The Girl Who Hits Joey” (Aired: 02/18/99)

Joey dates a girl who punches him; Ross has trouble with his neighbors; Chandler tries to show his commitment.

Written by Adam Chase | Directed by Kevin S. Bright

This isn’t one of the truly great or unforgettable episodes on this list, but each of its narratives is notable to some degree. The titular A-story with Joey and Soleil Moon Frye as the woman who loves to playfully punch him (to his obvious displeasure) is gaudy and gets easy laughs from its physicality, especially when Rachel kicks back. That supplies the show with some surface laughs. The subplot with Ross making enemies of the rest of his new neighbors in the building — including Willie Garson — is a great middle-of-the-road use of his character in a grounded, believable, comedic premise, and it’s bolstered by the incorporation of Phoebe, for the Ross/Phoebe pairing (something that’ll develop even more in the years ahead, from the way that Monica/Chandler naturally shift the ensemble and force new cast combinations in story) is one of the show’s most amusing dynamics. That’s what I always enjoy most about watching this entry. However, it’s the Chandler story that I think deserves our attention in a critical study, for the simple idea of his having to deal directly with his well-established commitment phobias (something that a relationship naturally calls to the fore) indicates how the Monica/Chandler romance can contribute to his growth. Here, because he loves Monica so much — and has been committing to her gradually — he’s willing to take a step for which he’s not quite ready. That’s real evolution… but it also indicates a problem. If Chandler is willing now to commit to marriage (and the finale also suggests as much, even if the development is unmotivated), then his arc is basically stalled until he does get married, for he’s already narratively ahead of the show. (This is one of the primary reasons that Seasons Six and Seven will feel stagnant; stay tuned…)

09) Episode 113: “The One With The Cop” (Aired: 02/25/99)

Phoebe pretends to be a cop; Ross and Rachel struggle to deliver his new couch; Joey thinks he has a crush on Monica.

Story by Alicia Sky Varinaitis | Teleplay by Gigi McCreery & Perry Rein | Directed by Andrew Tsao

Michael Rapaport makes his first of four appearances as Gary the Cop, Phoebe’s first serious love interest so far. (Well, the show would argue that David was serious, but I maintain that his one-off turn in Season One didn’t effectively make that case.) And while I don’t believe Gary’s installments are exceptional — and vociferously think the way his arc concludes is abrupt and tonally ill-managed — it’s vital to see Phoebe taking steps towards one day possibly having a family of her own… But I’m getting ahead of myself; this entry first introduces them, via an amusing Victory-In-Premise where she picks up a lost police badge and pretends to be a cop. It’s easy, breezy. Meanwhile, the Joey story, of him thinking he likes Monica (another tease) but actually realizing that he craves the kind of serious relationship that Chandler has with her, is a great episodic play towards his overall objective, which is rooted in the kind of selfless love that he idolizes. (If only it was followed up later this year…) However, once again, we turn to Ross for what makes this excursion memorable, as his attempt to move a couch into his new apartment has yielded a famous scene. You know it — this is the PIVOT! PIVOT! episode, and Schwimmer is terrific in the hilarious slapstick centerpieces. (Also, this scene features Rachel — in a rare Ross/Rachel story from an otherwise Ross/Rachel-lite era.) Roundly interesting.

10) Episode 116: “The One Where Ross Can’t Flirt” (Aired: 04/22/99)

Ross tries to flirt with the pizza delivery girl; Joey’s grandma comes by to watch his TV appearance.

Written by Doty Abrams | Directed by Gail Mancuso

Truthfully, I can’t pretend this is one of the list’s funniest. But as a nearly real-time offering, this is the smallest episode from a season that is getting larger in every possible way, and just like the best outings from years ago (such as the Thanksgiving shows and the aforementioned “…No One’s Ready”), this entry thrives because it gives us what we really want: the six of them all together in the same room at the same time. By virtue of this design, it’s an installment worth noting. Fortunately, there’s also enough comedy here to justify including it, like in the A-story with Ross, who is a terrible flirt (something we could have intuited from seasons past) — another place for Schwimmer to do shtick — and the B-story with Joey and his grandma, whom he doesn’t want to learn that his bit part on Law & Order has been cut. Meanwhile, although the story with the women and the earrings isn’t funny, it makes use of both Rachel and Phoebe’s characterizations, and like the other plots for Ross and Joey, it displays them well without broadening them (unlike EVERY OTHER SCRIPT at the end of Season Five). So, thank goodness for this chosen smallness, for while it may be a gimmick in its own right, it doesn’t play into the era’s unfavorable trends. (Lilyan Chauvin and Kristin Dattilo guest.)


Other notable episodes that merit a look include: “The One After Ross Says Rachel,” which is an adequate continuation of the finale and works until the contrived last scene where it tries to convince us that Ross and Rachel would decide to go on his honeymoon together, “The One Where Phoebe Hates PBS,” which boasts an interesting Joey/Phoebe story and some fun hijinks for Monica/Chandler, “The One With Chandler’s Work Laugh,” which contains the annual Janice guest stint (as she dates Ross — funny idea, strained credulity), “The One With Joey’s Bag,” which employs three workable stories (one emotionally resonant, two purely comedic) but lets them down within a mediocre teleplay, and “The One With Rachel’s Inadvertent Kiss,” which claims Victorious Premises for Rachel and Joey.


The Island of Better-Than-Their-Episode Stories:

  • “The One Where Ross Moves In” — Ross moves in with the guys and annoys them
  • “The One With The Inappropriate Sister” — Phoebe collects money on the street


*** The MVE Award for the Best Episode from Season Five of Friends goes to…..

“The One Where Everybody Finds Out”



Come back next week for Season Six! Stay tuned tomorrow for a new Wildcard Wednesday!

14 thoughts on “The Ten Best FRIENDS Episodes of Season Five

  1. i luv this season b/c it was brilliant to put monica-chandler together . many great eps because of it . it gave the show freshness .

    interesting that u dont like the vegas eps . i think s6 premiere is bad and the ross-rachel cliffhanger is 2 but dont mind the show actually . phoebe is funny

  2. I’m going to have to disagree with you regarding the finale. I thought it was quite funny and I felt like the cliffhanger worked and provided some funny moments in season six. Is the finale your least favorite this year?

    • Hi, Charlie! Thanks for reading and commenting.

      I dislike the finale intensely and think it’s up there with the year’s worst, if only because FRIENDS puts so much stock in its season-enders and therefore can’t afford to churn out material that’s less believable and character-driven than it needs to be.

      To elaborate on why I find it disqualifying… I don’t buy that Monica and Chandler would make the decision to get married based on a craps game, I don’t think Ross and Rachel getting drunk is enough to motivate an off-screen decision to wed — primarily because the year has all-but-abandoned tracking their feelings for one another — and I blanch that the subplots for Phoebe and Joey highlight their new aggrandized-and-unmotivated personas (she’s harsh; he’s imbecilic).

      You see, for me, it isn’t just the story-driven nature of the forced Vegas vacation or the machinations of the unearned cliffhanger that’s most bothersome — it’s the exorbitantly broad and unrealistic way these characters are depicted throughout these story beats… However, it should be noted that this is a shift that isn’t unique to the finale, and spans, again, the year’s last five episodes.

      (To that point, I actually like the half-hour that precedes the two-part finale, “The One With Joey’s Big Break,” even less. I appreciate that its A-story tries to find some emotional support within Joey and Chandler’s friendship, but the telling is hampered by one of the most comedically labored teleplays of the year, with TERRIBLE subplots for the others — especially Ross/Phoebe. It’s rivaled, in my mind, only by “The One with the Yeti,” which doesn’t showcase any of the regulars favorably — especially Rachel — and is another candidate for my seasonal least favorite.)

      Meanwhile, I’ll save my thoughts on this cliffhanger’s aftermath for next week; stay tuned…

  3. This is a really good year because Monica and Chandler bring excitement. I love the way that the show builds to the revelation where everyone finds out (in the year’s best episode to be sure.) But I also agree that the final few episodes are disappointing and count the Vegas finale as one of the worst. With London, at least we’d had a good feeling of how Rachel was feeling and why she would go to the UK to pursue Ross. Here, they’re just drunk. And that’s stupid and not character-driven.

    Season Six is one of my least favorites, so I’ll be curious to see what you say about it next week. (Judging by this post, I think you feel similarly.)

    • Hi, Elaine! Thanks for reading and commenting.

      Yes, it should come as no surprise that I find Season Six to signal a significant comedown in quality; stay tuned…

  4. Great commentary. Your point about Chandler being ahead of his arc really made me think about the next few seasons and why they’re not among my favorites. I look forward to reading more of your thoughts! This is some of the best criticism I’ve ever read about this series.

    • Hi, Deb! Thanks for reading and commenting.

      I appreciate your very kind words and am glad you’re enjoying these posts!

  5. I’m in the minority I guess but I don’t like how the Monica-Chandler relationship impacts both characters. She becomes a crazy shrew and he becomes a typical addled spouse (even before they get married). So by this time I think the show’s best days are behind it. And I agree with you about Vegas–it’s a far cry from what this show used to be, even last season!!

    I do love certain episodes here though like TOW Everybody Finds Out and TOW The Cop. Also I’m glad to see you include TOW The Girl Who Hits Joey. I think the Ross-Phoebe story is hilarious. And I think TOW Ross Can’t Flirt is an underrated gem. It’s no TOW No One’s Ready but its more evocative of that kind of simple storytelling that I like.

    • Hi, GaryK328! Thanks for reading and commenting.

      As noted, I appreciate how the Monica/Chandler pairing serves the show’s premise-based needs while also addressing both of those characters’ previously established emotional arcs. But I agree that the accompanying shifts in the characterizations as a result of their coupling (for pretty much everyone but Chandler, whose evolution I find to be, for the most part, more trackable) is a mixed bag of positives and negatives; stay tuned for more…

  6. This has to be my favorite season because of Monica and Chandler. Ross and Rachel had started to wear on me with all the melodramatics. Monica and Chandler reinvigorated the show for me. Thanks Jackson for the great commentary as usual.

    • Hi, Smitty! Thanks for reading and commenting.

      Yes, this year is a breath of fresh air — especially after Season Four!

  7. Hi, Jackson. Interesting analysis of a series I’ve never watched nearly as much as SEINFELD (and I didn’t catch on to SEINFELD until nearly the end of that series because I first discovered it in late-night syndication).

    I apologize about commenting here on a couple of episodes from other seasons here, but I did enjoy part of an S3 episode you said you hated, “TOW Phoebe’s Ex-Partner”, just for the silliness of the cat litter commercial that came out of “Smelly Cat” and for Phoebe’s bitter reaction song to her ex-partner that results from it. I guess I like little moments more than full episodes if the moments make me laugh enough.

    My other “out of season” comment here comes as another example of David Schwimmer’s great slapstick comedy ability, which you mention a couple times here. I forget the episode name, and I don’t feel like digging for it here, but I love the late season bit where Ross tries out a tanning booth and has trouble counting to the right time to turn around (“One Mississippi…Two Miss…Arrgh!”) and ends up being sprayed in the wrong places. I can’t remember any other of that episode’s subplots, but it showed that he could still carry a good comedy scene to the end.

    • Hi, Jon! Thanks for reading and commenting.

      I don’t hate “The One With Phoebe’s Ex-Partner,” but I think it’s a rare occasion from the third season where all three stories are strained to some significant degree. I agree that you’ve pinpointed the two funniest bits from the episode, although I think the A-story nevertheless suffers because we already know, like Phoebe, how it’s going to end (and the telling does little to assuage this limiting predictability). It’s therefore hard to stay emotionally invested.

      Also, the installment you’re thinking of with Ross’ tan is titled, no shock, “The One With Ross’s Tan,” and it’s from Season Ten. Stay tuned to find out if it makes that week’s list… (Spoiler alert: it will!)

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