The Ten Best CHEERS Episodes of Season Five

Welcome to a new Sitcom Tuesday! Today we’re continuing our coverage of the best episodes from Cheers (1982-1993), one of the most consistently written situation comedies of all time and second only to I Love Lucy as my personal favorite. I’m pleased to announce that every episode has been released on DVD. 


The staff and regular patrons of a neighborhood Boston bar share the highs and lows of their daily lives. Cheers stars TED DANSON as Sam Malone, SHELLEY LONG as Diane Chambers, RHEA PERLMAN as Carla Tortelli, JOHN RATZENBERGER as Cliff Clavin, GEORGE WENDT as Norm Peterson, WOODY HARRELSON as Woody Boyd, and KELSEY GRAMMER as Dr. Frasier Crane.


The Diane era of Cheers comes to a gripping conclusion in this, the show’s fifth season, which is perhaps the funniest and most classic-filled to date. The gradual broadening of the series’ humor has reached a nice balance with the writing’s hallmark intelligence, culminating in a season filled with fresh ideas, great character moments, and ultimately, a decent swan song for the show’s most complex character. However, for those fans, like myself, who revere the early seasons for the respect the writing bestows upon the audience — rarely asking that we suspend our disbelief beyond the heightened trivialities that comprise everyday living — this is the year where it’s imperative to accept that the series, now a smash hit, is not only leaving the bar with regularity (and some episodes are set almost entirely elsewhere in the quest for continually fresh stories), but also transitioning its focus from expert character moments to expert laughs (as if you didn’t quite get the memo in the latter half of Season Four). In other words, by Season Five, comedy has become more of the guiding factor in each script, necessitating an increase in the exaggerated farce, the broader beats, and the occasional breaches of truthfulness. However, the show mitigates this hurdle by maintaining a fairly consistent level of quality (which nevertheless leaves room for the occasional dud), and by presenting humor that makes this evolution seem conclusively worthwhile.


But all of these changes are overshadowed by the inevitable departure of Diane, which, despite not being firmly made public until the middle of the ’86-’87 season, actually seems a forgone conclusion from the year’s premiere. Interestingly, once Long made definite to the producers her intention to leave the series (in December of ’86, after the engagement was written and filmed), rumors circulated that the show was going to make Diane increasingly unlikable as a subliminal tactic to break the audience’s investment in the character. Even today, there are many fans who believe that the series does make her progressively more annoying after this development, and even I must admit to feeling similarly during earlier viewings. However, watching the entire series in chronological order and in a more focused context, I now don’t think Diane’s personality is written any differently post-engagement — well, except for the fact that her gradual assimilation into the group, a major arc in the first two seasons, goes into total regression, as she begins to feel more and more like the outsider. (But this idea was already part of several stories in Season Four and noticeable in the scripting of many of the fifth season’s earlier entries — likely due to what’s discussed below.)


Rather, I think Diane is more unlikable (in fact, VERY unlikable) in the first half of the season — before anyone knew officially that Long was leaving — in which Diane actively pursues Sam with an intensity that’s not only too extreme to be relatable, but also comes dangerously close to alienating an audience who is otherwise crusading for their reunion. But because the last two years that Sam/Diane spent apart were more angled by his lingering pursuit of her (or his unspoken knowingness that they would fall back into one another), I can understand the decision to make her, once again, the driving force in a reconciliation. In this case, it wouldn’t be Sam’s lust (or even Diane’s lust) that was drawing them to a reunion — it would be her staunch belief that they were soulmates. It’s actually a sizable change, and I think it makes for a difficult point to accept: now she’s absolutely sure that they’re meant to be — with not even some doubt, like she held in Season Two? You see, it’s not completely buyable, and as a result, we hold it against her, especially when her behavior verges on the stalker-ish extreme. Additionally, we come to like Sam way more than we like Diane; the balance that once existed, and was probably more towards her favor in the first two seasons, has been altered irreparably.

CHEERS, (from left): Ted Danson, Shelley Long, I Do, Adieu, (Season 5, aired May 7, 1987), 1982-93. © Paramount Television / Courtesy: Everett Collection

But that’s not all; after more than four years of their back and forth, the pair’s dynamic is starting to grate, and that’s really the bigger problem with the continued shenanigans of Season Five’s Sam/Diane arc. (In this regard, it’s more understandable why the show felt that it needed to progress the relationship — even at the temporary expense of Diane.) While the first half of the year is the final chapter of this will-they-won’t-they saga, once Sam and Diane are engaged, a development that isn’t totally logical but ultimately works because of the humor with which the show imbues each episode, the scripts are allowed to explore an extended arc that’s fresh, fun, and gives the audience a break from the contrivances that came before. And although we know the end is nigh for Sam/Diane, we also get a tiny reward in their seeming half-season of happiness. This doesn’t completely fix what was done to Diane and their relationship in the beginning of the year, but the lack of sustained irrationality makes for provisional enjoyment — both for those who love them together, believing the development to be right, and also to those who appreciate their dynamic, but still think the development requires a lapse of logic.


Yet while many of the Sam/Diane offerings remain the highlight of the season (because again, the show puts most of its energy on them and therefore their installments have a higher chance of working), the ensemble continues to assert its importance, even besting Sam and Diane in certain outings, while a lot of great decisions are being made to prove that the show can and will have a life after Diane — like mining comedy from Frasier’s relationship with Lilith (Bebe Neuwirth, who appears twice in Season Five) and the expanding universes for each character; we meet Cliff’s mother, see Carla’s new house, visit Norm in the workplace, etc. And, as noted in the beginning of this reflection, there are a lot of classics here. In fact, this year holds the most classics we’ve seen yet! So all of the above nitpicks and complaints must be taken within the context of a season that is still superiorly rendered. As usual, I have picked ten episodes that I think exemplify this season’s strongest installments. For new fans, this list will give you a place to start. For seasoned fans, there might be a few surprises.


Here are my picks for the ten best episodes of Season Five. (They are in AIRING ORDER.) Every episode this season is directed by James Burrows, except two (neither of which has been highlighted below).


01) Episode 97: “The Cape Cad” (Aired: 10/02/86)

Diane follows Sam and his date up to Cape Cod.

Written by Andy Cowan & David S. Williger

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If you’ve been following these posts, you’ll notice that each season has gradually taken us further outside the bar, and as noted above, by Season Five, many of the episodes on today’s list (including this one) spend a significant portion of the action on separate sets. This particular show, which begins immediately after the premiere as Diane accepts Sam’s proposal — even though he’s rescinded it following her initial rejection, concerns Diane’s stalker-ish decision to go up to an inn on Cape Cod where Sam has taken a date. When Sam’s girl leaves early, he tries to keep Diane from finding out. The whole thing is overly farcical, and in fact represents a type of storytelling I wouldn’t have accepted from the series before 1986, but with great laughs and some memorable guest stars, this becomes a hysterical entry, trumping the obvious handicaps.

02) Episode 99: “Abnormal Psychology” (Aired: 10/16/86)

Frasier and Lilith find themselves attracted to one another.

Written by Janet Leahy

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Following her brief appearance last season, Bebe Neuwirth returns as Dr. Lilith Sternin in this episode centered entirely around the passionate undercurrent that exists in her contentious relationship with Dr. Crane. Their lust/hate dynamic makes for fun parallels between Sam and Diane’s, but in this case, both Frasier and Lilith are highly intellectual, allowing for a more evenly matched mutual desire for superiority. The transformation of Lilith and Frasier’s visceral response to one another is a fantastic sight gag, and the entire bar getting hot by watching the two make gaga eyes at each other on live television (while talking about psychiatry, mind you) makes for some really boffo laughs. Among both the season’s (and even the series’) absolute funniest offerings, this was a definite MVE contender. A favorite; a classic!

03) Episode 102: “Young Dr. Weinstein” (Aired: 11/13/86)

Sam masquerades as a doctor to bump Diane’s reservation at a fancy restaurant.

Written by Phoef Sutton

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Sutton’s first script following “Don Juan Is Hell,” a highlight from the previous season, this is one of those exquisite teleplays that makes me wish that I gave out more than one MVE per year. The story involves Sam cancelling a reservation that Diane and a date have made at an exclusive restaurant so he can steal their table while under the name of a renowned heart doctor, just to get back at Diane for her initial boasting. This naturally leads to the delectable moment when Diane is denied a table, while Sam is escorted in without hesitation. However, it’s really the dialogue that makes this episode crackle and pop, as the laughs are rapid and without hesitation. My favorite joke involves Diane’s insistence that Sam and his date “sashay over” to something more their style, “the colonel’s.” Hysterical entry – sublime from open to close!

04) Episode 104: “Thanksgiving Orphans” (Aired: 11/27/86)

The Cheers gang has Thanksgiving at Carla’s.

Written by Cheri Eichen & Bill Steinkellner

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What can one say about a TV classic — one that often makes “best of” lists? I discussed this installment years ago, briefly, as one of the finest Thanksgiving themed sitcom episodes of all time. Now I’m going to double down and report that this may actually be the finest Thanksgiving themed episode of all time. Although most of the action occurs outside of the bar, all of the regular characters are together (at Carla’s new house) and interacting as they normally do — with logic and hilarity. The bit involving Diane and her professor’s annual Thanksgiving feast is amusing, as is the final gag involving a pie-faced Vera (it’s the closest we’ll ever come to seeing her). But of course, the main course is the iconic food fight that erupts at the dinner table as the group waits for the darn turkey to finish cooking. The cast’s evident enjoyment is infectious, and the food fight is such a fun and unique centerpiece to an episode that was already so well written from the start. My favorite of the year — and the one here that most proves Sam and Diane are no longer the show’s sole recipe for success.

05) Episode 105: “Everyone Imitates Art” (Aired: 12/04/86)

Sam gets a poem published in a magazine while Diane’s is rejected.

Written by Heide Perlman

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One of the appealing factors about this episode is that, in a time in which Diane harasses Sam, he now gets to have a little fun with her. As a result, she’s much more likable — even when crazed and caffeinated — than in any of the offerings above. Also, this is another excellently written entry, concerning Diane’s poem being rejected from publication while Sam’s submission is accepted. That’s an easy, but delicious, idea for a story right there. But when Diane reads Sam’s piece, she knows she’s heard it before, leading to a feverish quest to prove that Sam is a plagiarist. Of course, the twist is that Sam submitted one of the old poems she had written for him, meaning that Diane really did get published after all. It’s a bit cutesy, but because the brief possibility of Sam being a better poet than Diane is dangled, it’s all comedically welcome. Fun.

06) Episode 108: “Chambers Vs. Malone” (Aired: 01/08/87)

Sam and Diane end up in court after a botched proposal.

Written by David Angell

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Okay, this episode is problematic. Diane spends the entire first act insisting that Sam will propose to her today. It’s the most obnoxious she is all season (for all the reasons discussed above in my intro), especially because when Sam does propose, she turns him down — again. I suppose her conduct is so frustrating that we can’t help but laugh. But then the question of Sam physically hurting Diane is raised, and that’s an even more difficult line to tread, especially because, no matter how they’ve written her, that idea is not funny. However, by the time we reach the court room scene, the show is in full farce mode (with big laughs everywhere), which seems to justify all that came before. It’s gimmicky, it’s broad, it’s nonsensical. But it’s funny. And because this is such a big moment for Sam and Diane, the larger-than-life-ness is warranted.

07) Episode 113: “One Last Fling” (Aired: 02/12/87)

Sam and Diane give each other a 24-hour hall pass.

Written by Cheri Eichen & Bill Steinkellner

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A lot of the humor in this episode is built entirely on the premise. It’s another pretty easy one from which the show can get laughs — Diane grants Sam a 24-hour break to sow his wild oats before finally committing to her. But when she announces that she too will do the same, he spends his whole 24 hours spying on her. It’s the kind of fare that works well for these two, even though we’ve long become accustomed to what’s likely going to (and does) happen. I’m actually more intrigued by the build-up that gets us there, in which the guys throw Sam a bachelor party, where Woody has the (dumb) idea of having Diane jump out of a cake dressed as a stripper. The bit is very funny, because we know what’s coming, while Sam, who’s shooting his mouth off about being tied down, doesn’t. Another smart Eichen/Steinkellner script.

08) Episode 115: “Dinner At Eight-ish” (Aired: 02/26/87)

Sam and Diane come to dinner at Frasier and Lilith’s place.

Written by Phoef Sutton

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Because the meat of this story takes place not at the bar, but on the single set of Frasier and Lilith’s apartment (the pair have just become POSSLQs), this installment, during those apartment segments at least, feels like the one acts that used to typify the early seasons of the show. It’s just those four characters, arguing about various secrets they’ve kept from one another — specifically, Lilith’s not knowing about Frasier’s serious relationship with Diane (or the fact that they also lived together at one point). Sutton’s script, once again, is a comedic delight, with joke after joke after joke, and all of them true winners, making for yet another one of the smartest offerings from the season, eschewing cheap humor for bits that are rooted in character and their established histories. One of my personal favorites — all jokes from character beats!

09) Episode 115: “Simon Says” (Aired: 03/05/87)

A marriage counselor predicts doom for Sam and Diane.

Written by Peter Casey & David Lee

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And if there weren’t enough episodes around to make choosing an MVE a difficult feat, here comes this installment, guest starring John Cleese (yes, the John Cleese) as a marriage counselor friend of Frasier’s who agrees to give Sam and Diane a session. Naturally, he predicts nothing but disaster for the pair and encourages them not to marry. Naturally, Diane won’t accept his verdict and believing him to be merely testing their resolve, decides to prove to him that his rushed judgment is indeed inaccurate. Everything that’s wrong about the Sam and Diane relationship is revealed in their session with Cleese’s character, and the unfolding ramifications are a veritable scream, perfectly proving his initial point. Cleese won an Emmy for his work in this hysterical episode, which again, is another one of my top favorites from the entire series.

10) Episode 121: “I Do, Adieu” [a.k.a. “I Do And Adieu”] (Aired: 05/07/87)

Diane has an opportunity that may interfere with her plans to marry Sam.

Written by Glen Charles & Les Charles

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Diane’s last episode as a series regular is hard to view comedically because, frankly, we all know what’s coming, and to everyone but Carla, it’s not a very amusing prospect. The idea of having Sumner return is a nice callback to her character’s introduction, and while the rationalization of not being able to both get married and write a novel isn’t fully reconciled within the script, the idea of having this be the only time Diane leaves Cheers with an intent to return is powerful, because it’s different from all the other times where she vows otherwise — and Sam knows it. Sam’s daydream of their life as geriatrics has some laughs, and their final scene of dancing together to Irving Berlin’s “What’ll I Do?” is a tearjerker. Ultimately, a fitting end to this breathtakingly nuanced character’s tenure, bringing back the humanity that this season reduced.


Other notable episodes that narrowly missed the list above include: “The Proposal,” which is worthwhile mostly for the boat scene where Sam is enraged when Diane turns down his proposal (a popular entry that I don’t think is well written enough to overcome the story beats), “Knights Of The Scimitar,” which features some engaging Sam/Diane moments and a moderately amusing Cliff/Norm story, and “Diamond Sam,” in which Sam overcompensates after buying Diane a fake diamond engagement ring (a few nice laughs here, but some saccharine too). There are several other episodes of “honorable mention” quality, but only the three above were seriously considered for inclusion on today’s list.

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While most of the cold opens from Season Five are sufficiently enjoyable, none are of exceptional merit or memorability to warrant mention. Stay tuned next week for Season Six!


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

“Thanksgiving Orphans”

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Come back next Tuesday for the best from the sixth season! And tune in tomorrow for a new Wildcard Wednesday post!