The Ten Best THE NANNY Episodes of Season Five

Welcome to a new Sitcom Tuesday! This week, we’re continuing our coverage on the best of The Nanny (1993-1999, CBS), which is currently available on DVD and HBO Max.

The Nanny stars FRAN DRESCHER as Fran, CHARLES SHAUGHNESSY as Mr. Sheffield, DANIEL DAVIS as Niles, LAUREN LANE as C.C., NICHOLLE TOM as Maggie, BENJAMIN SALISBURY as Brighton, and MADELINE ZIMA as Gracie. With RACHEL CHAGALL as Val, ANN GUILBERT as Yetta, and RENÉE TAYLOR as Sylvia.

As discussed last week, I think the criticisms typically reserved for both this and the final season of The Nanny should be pushed up to include Four, the year where the series undermined its characters and alienated its premise from story by not pairing its core couple when the plotting warranted a shift, prolonging a disruption to their “status quo” in an attempt to preserve it… even though, failure to follow this natural progression corrupted its usage thereafter. In fact, a lot of the complaints with Five and Six operate under the series’ own fallacy — that the show no longer works because the leads are coupled and the premise is over. But, again, I disagree. The problem with this series’ pairing of Fran and Maxwell is NOT that they’re paired. That’s silly; we’ve seen enough sitcoms with rom-com elements — CheersFriends, That ’70s Show, etc. — to know that motivated changes in relational dynamics increase dramatic tension, as there’s new situation-based fodder for episodic story, meaning a Fran/Maxwell romance should still evoke the premise within plot, only now in a fresh way. Indeed, the problem with how this series pairs its central duo is that, once it does so, it doesn’t explore how this evolution affects the characters. That is, instead of stories where Maxwell and Fran must adjust to being romantic, enduring interpersonal conflicts with each other, drama with other members of the family, and the basic clash of “his world” vs. “her world,” The Nanny continues to traffic in gaudy gimmicks with flashy guest stars, ridiculous centerpieces where Fran Drescher hopes to channel Lucille Ball (but gets the Lucy Carmichael version — the one free of any grounding objective that could buyably link action to character), and outrageous narrative notions that aren’t driven by these leads. So, the opportunity for good sitcommery from this earned movement is squandered, and all it brings is BAD sitcommery… not to mention predictable beats in a narrative arc — engagement, marriage, and (next season) pregnancy: formulaic sitcom fare that isn’t much enlivened by the particulars of this “situation.” Oh, sure, there are a few episodic distinctions near the end of Five — after a terrible first half that awkwardly keeps the couple’s relationship in suspended animation, not quite rejecting it, only pausing it for the next Sweeps — but there’s just not enough credible situation comedy here, especially compared to the first three years.


01) Episode 102: “The Morning After” (Aired: 10/01/97)

Mr. Sheffield distracts Fran with a decorating assignment after their romantic encounter.

Written by Caryn Lucas | Directed by Dorothy Lyman

Season Five’s premiere is less egregious than its predecessor’s, for it explicitly has Mr. Sheffield conspiring to distract Fran from following up on their romantic encounter in Four’s finale, allowing the main characters to have a more consciously active participation in the series’ stalling tactics than they did before. In that regard, it’s less insulting to the audience and not as damaging to the leads — frankly, that damage is already done — and in fact, this funny script actually gets some comedic mileage out of the idea, thanks in large part to a guest appearance by Roseanne Barr (fresh off her own sitcom) as Fran’s decorator cousin. She has a great rapport with the Fine women, and literally helps divert us — better than Jason Alexander in Four’s opener — from the series’ continued slow-walking of its primary coupling.

02) Episode 103: “First Date” (Aired: 10/08/97)

Mr. Sheffield and Fran’s first date is ruined by her negative history with Elton John.

Teleplay by Frank Lombardi | Story by Sarah McMullen and Frank Lombardi | Directed by Dorothy Lyman

If the premiere sought a little buffer before diving into the idea of Fran and Mr. Sheffield being in an exclusive relationship, this year’s sophomore outing looks to add some genuine movement, as the pair goes on their first official date — well, with the rest of the family in tow. This is a big moment for the twosome, and considering that the trajectory of their closeness is part of the series’ premise, it looks as if this might be a classic show… But alas, The Nanny reveals everything we discussed above to be true, forsaking this opportunity to find conflict related to a change in the leads’ “situation,” and instead pushing a gimmicky Lucy-esque narrative where Fran disguises herself as Grandma Yetta so Elton John won’t recognize her as the annoying woman who once said “yoo-hoo” to him. Of course, the sight of Drescher in Yetta’s garb is inherently funny… yet this is not great situation comedy, for the story is not derived from differences between the leads or their given circumstances, but from some external scenario that also enables a stunty cameo. It’s exactly what these last few years all do, in a nutshell.

03) Episode 111: “From Flushing With Love” (Aired: 12/17/97)

Niles sides with C.C. against Fran when she gets a weekend off and he doesn’t.

Teleplay by Dan Amernick & Jay Amernick | Story by Sean Hanley and Dan Amernick & Jay Amernick | Directed by Dorothy Lyman

The first half of this offering is far superior to the latter, where the family takes a boat ride at Niagara Falls and Mr. Sheffield is so moved that he proposes marriage… only Fran couldn’t hear it because of the loud waterfall. That’s a gaggy notion that attempts to find humor in the series’ continued prolonging of forward momentum in their relationship — which, incidentally, has been in limbo after the Elton John entry, for they’re not dating exclusively… which is, again, a missed opportunity. (That is, why go from quasi-single to engaged with no in-between? Think of all the stories that are ignored!) However, I really highlight this installment for the first half, where Niles teams up with C.C. against Fran because he’s mad that she always gets her way with Mr. Sheffield — a fun idea that reverses their usual dynamic, and thus plays upon our knowledge of the “situation” as it typically exists. (Note: Spalding Gray’s Dr. Miller appears.)

04) Episode 112: “Rash To Judgment” (Aired: 01/07/98)

Another romantic date between Fran and Mr. Sheffield is ruined — this time by a rash.

Written by Ivan Menchell | Directed by Dorothy Lyman

Still in some kind of nebulous state, Fran and Mr. Sheffield go out on another date — and once again, this conflict comes not from anything related to their characterizations or the premise that creates for them a “situation,” but from some trivial episodic roadblock: Fran has gotten a rash from her mother’s cooking. And after she goes to get the rash treated — by an inept doctor played by Happy Days’ Scott Baio — she has an allergic reaction and swells up, with Drescher donning prosthetics for an over-the-top sight gag that, yes, earns easy laughs… but, as usual, is unideal sitcommery, for movement in the central relationship is sidelined and prolonged… but not for something that actually stems from the characters and how they’re defined — only from this comical gimmick. (Michael Bolton and Fred Stoller also guest.)

05) Episode 116: “The Engagement” (Aired: 03/04/98)

Word spreads fast that Maxwell is finally ready to propose marriage to Fran.

Written by Rick Shaw | Directed by Dorothy Lyman

As the title indicates, this is the “big event” show where the leads’ bond officially changes — following the dreadful prior entry where Maxwell nevertheless re-confessed his love for Fran and didn’t retract it — and so there’s an inflated sense of value for both character and premise that elevates this one above a lot of the year’s output. Fortunately, its script is pretty strong too — sentimental clip packages aside, and notwithstanding the contrived conflict where Maxwell is mugged (another dilemma that is not motivated by the characters) — for there are some great bits, like the fantasy sequence where Fran imagines what she, Maxwell, C.C., and Niles will look like in old age, and a wonderful phone call scene, where news of his upcoming proposal spreads through the family. It’s a lot of fun — one of the better teleplays for a segment that is naturally momentous, finally evolving (believably) the characters’ status quo.

06) Episode 117: “The Dinner Party” (Aired: 03/11/98)

Fran feels out-of-place now that she’s officially introduced into Maxwell’s ritzy world.

Written by Ivan Menchell | Directed by Dorothy Lyman

This is the first of three installments that come close to laudable sitcommery, with stories that examine how a change in the central relationship could affect the series’ premise at large. In other words, these episodes manage to involve the show’s “situation” by using this year’s big development, proving that a tweak in a rom-com’s status quo can actually work for a series, by increasing narrative opportunities connected to the characters and their dynamics (which, in the case of The Nanny, speaks directly to the premise). This particular outing explores the prospect of Fran forever being a fish-out-of-water in Maxwell’s world, as her formal introduction as his soon-to-be-wife is met with snobbery and rejection. That’s a rich conflict that engages their premised differences, and while I’m less enthused about the climax where Fran is nice to a homeless man (Dick Martin) who turns out to be an eccentric millionaire — that’s all led by coincidence — at least there’s something of the right idea before it, indicating that The Nanny very well could have maximized its core coupling for true situation comedy.

07) Episode 119: “The Reunion Show” (Aired: 03/25/98)

Fran and Maxwell prepare for their future as a couple — like whether or not they’ll have kids.

Written by Suzanne Gangursky & Sean Hanley | Directed by Dorothy Lyman

With the engagement still fresh, this series offers another rare excursion that can be celebrated as actual situation comedy, for after an initial scene with Fran attending her high school reunion — where Ray Romano makes a cameo as Ray Barone — Fran and Maxwell talk about some of the important things that will change in their lives after they marry… with the main topic being whether or not they’ll have kids. Now, we pretty much expect her to get pregnant — she wants it, and this sitcom already doesn’t know how to handle their coupling unless it’s funneling them into an engagement arc, so we can assume another unimaginative storyline will follow — but it represents an opportunity for the series to mine drama related to this new development in their “situation.” Similarly, the subplot where Gracie fears she’ll be sent to boarding school is a good example of how this year could have concocted more stories featuring the kids, and how they are adjusting to this new arrangement. No, this isn’t a stellar half hour, but it’s dramatically rooted in the series’ circumstances — and that’s a rarity. (Leila Kenzle also appears.)

08) Episode 121: “The Pre-Nup” (Aired: 04/29/98)

Fran and Maxwell disagree over whether she should sign a pre-nuptial agreement.

Written by Frank Lombardi | Directed by Peter Marc Jacobson

My choice for this season’s Most Valuable Episode (MVE), “The Pre-Nup” is the third and final outing on this list that I think actually attempts to examine how this seminal change in the main couple’s relationship affects their broader “situation,” utilizing known elements of the premise for a story that’s directly related to The Nanny and its basic identity. It starts with a conflict between Fran and Maxwell over a pre-nuptial agreement — a point of contention that makes sense, given the class disparity that is a big part of their dynamic, referencing not only the fact that he was/is her boss, but also that she is far away from her upbringing when inside his wealthy, upper-crust world. It’s great to see these ideas come back up again in story — along with the notion that, despite her closeness to the kids, she’s not actually their mother, she’s just a “proxy mother.” That’s addressed when Brighton is at the hospital and Fran can’t get in to see him. Naturally, she dresses like a nun to sneak in — a display of this year’s comic ethos and willingness for broad physical comedy — but it’s not a threat to the show’s aesthetic realism, because it’s supported by an aspect of the premise: her love for the kids, even though, again, she’s not their mother… well, until the end of the show when plans are made for her to adopt them. So, this is an above-baseline sample of the series, for it’s one of the few installments from The Nanny’s last few seasons that is willing to explore an evolution in the lead characters’ relationship, thanks to a story that showcases how said evolution affects other aspects of the setup. And with the series’ bold sense of humor also reinforced — plus an indulgence of guests, as the high-energy Whoopi Goldberg also appears as a couples’ photographer (along with Ray Charles as Yetta’s recurring fiancé, and both Jessica Tuck and Kathryn Joosten in small roles) — both the “situation” and “comedy” feel specific here to this show and its own ideals.

09) Episode 122: “The Best Man” (Aired: 05/06/98)

Fran is worried that Maxwell will find out about her romantic past with his brother.

Written by Rick Shaw | Directed by Dorothy Lyman

Maxwell’s brother Nigel (Harry Van Gorkum) returns in this half hour, which exploits drama from the fact that he once proposed to Fran — in a subpar fourth season entry that primarily didn’t work because it shied away from a heavy emphasis on Fran and Maxwell… the latter of whom never found out about the potential coupling, until now. This offering somewhat makes up for Nigel’s previous showing, for at least its script is referencing a known happening — something that’s been established — as the foundation for its story, and with a conflict created via these relationships. So, this isn’t quite as gimmicky as many of the others produced here in Five, as it’s more rooted in elements unique to the series… okay, until the gratuitous Marla Maples cameo, that is, but beggars can’t afford to be choosers in Season Five.

10) Episode 124: “The Wedding (II)” (Aired: 05/13/98)

Fran has cold feet on the day of her wedding.

Written by Caryn Lucas | Directed by Peter Marc Jacobson

Season Five ends on Maxwell and Fran’s two-part wedding — which originally aired in a single hour-long block, and while the first half is largely dominated by clips, Part II treats us to the main attraction: the actual event. Now, there is an attempt to use Maxwell’s visiting sister to put doubts in Fran’s mind about the couple’s compatibility — it doesn’t quite land at this late hour, but it does speak to the two leads’ significant differences, suggesting that the show might be interested in pursuing more conflict related to said differences later on… Unfortunately, that will prove rare, but it’s a fascinating prospect, and adds a situation-based wrinkle to what is otherwise a fairly straightforward wedding show, enriched mostly by the big laughs that come from Fran’s outrageous family, especially, as always, Sylvia and Yetta. Other guests include Sophie Ward, Chris Hogan, and Darryl Hickman. (Incidentally, this original broadcast featured a quick but gimmicky I Love Lucy fantasy. It’s not in the syndicated, DVD, or streaming edits.)


Other notable episodes that merit mention include: “Call Me Fran,” where Maxwell starts calling Fran by her first name, revealing a relational shift, “Immaculate Concepcion,” which has a unique conflict predicated on the idea that the Sheffields might not be able to afford their lifestyle (with C.C. leaving her sanitarium stay — a clever cover for the actress’ real-life pregnancy — to sow additional doubt), and the aforementioned “The Wedding (I),” which has some laughs but is largely sentimental, incorporating plenty of flashback clips. Meanwhile, I’ll also take this time to cite “The Bobbie Fleckman Story,” where Fran Drescher has fun playing dual roles, “The Ex-Niles,” where Niles temporarily goes to work for Aunt Freida (Lainie Kazan), and “Fair Weather Fran,” which introduces Ray Charles in the recurring role of Grandma Yetta’s new fiancé — one of this season’s peripheral arcs.


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

“The Pre-Nup”



Come back next week for Season Six! And stay tuned tomorrow for a new Wildcard!

10 thoughts on “The Ten Best THE NANNY Episodes of Season Five

  1. I’ve enjoyed your coverage of THE NANNY. Gave me an excuse to watch this series again for the first time since it originally aired. Three thoughts I had watching season 5: 1) I guess there really is a limit to how long you can milk a “will they or won’t they” situation before the audience just loses interest; 2) You can almost forget Fran is still employed as a nanny, since in many of these later shows, the kids are lucky to get one short scene per episode, just to remind us they’re still around; 3) Maybe it’s just me, and I can’t explain why but the more I see of Sylvia and Yetta, the less I like them.

    • Hi, Randy! Thanks for reading and commenting.

      I agree with you — these are things we’ve been talking about since, in particular, Season Four…

      1) The manipulative narrative tactics that Season Four (and Five) employed to avoid evolving the series’ status quo — when the characters’ depictions already warranted a shift — undermined both their depictions and the premised central relationship, as strained logic halted the audience’s emotional investment and ensured that all sexual tension went limp.

      2) By now, the series is also no longer utilizing its “situation” often in story, for even after the central couple pairs — and there’s fresh narrative opportunity — it’s still not genuinely exploring how this development affects the leads and/or the various aspects of the premise. Instead, we get gimmicks like stunt casting and formulaic arcs — a cheap, bad form of situation comedy.

      3) Without the premised understanding of Fran’s family being an extension of her persona — via how she clashes *in story* with the rest of Mr. Sheffield’s world — the broad depictions of these peripheral players feel only like overused distractions, gimmicks in their own right.

      These are self-induced failures that relate to how THE NANNY is essentially offering poor situation comedy in the latter half of its run — a darn shame, given its otherwise smart design (and resulting early successes).

    • Hi, esoteric1234! Thanks for reading and commenting.

      What a nice compliment — glad you’re enjoying these posts!

  2. I remember watching the wedding live with the “I Love Lucy” scene–such an obvious comparison for the series by this point given Fran’s antics but very cool the way they did it with her literally inside the scene. I know it’s not in syndication but is it not on the DVD either?

  3. I’m not going to lie I’m not the most sentimental but the engagement episode was so well done

    Probably one of the episode I stuck to my mind

    • Hi, Track! Thanks for reading and commenting.

      Yes, if you’ve been rooting for the pairing of THE NANNY’s central couple, it’s certainly a memorable episode!

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