The 10 Best Episodes of ‘The Nanny’

Fran Drescher's seminal '90s series is finally available on DVD, and it's infinitely better than you want to give it credit for. Here are ten reasons why that is the case.

Out of all the famous sitcoms from the ’90s, The Nanny might just be the most underrated. With nostalgia for the last decade of the 20th century being exploited in fashion, music, and other art forms, it seems almost conspicuous that Fran Drescher’s CBS show doesn’t get more mentions. Perhaps its self indulgent camp, and the unique qualities of its leading lady — truly one of the boldest casting decisions made in any network television series — more often than not have reduced it to a curio. In part, this must have something to do with the fact that the show has remained largely unattainable since it went off the air in 1999. The Nanny still can be seen in syndication (it was rightfully acquired by LGBT cable channel Logo in 2011) but with the way viewers consume television, changing so drastically in the past few years, the fact that The Nanny isn’t available on any streaming service has left it into semi-obscurity.

At its core, the show was nothing more than another retelling of the Cinderella story, a middle class unemployed hairdresser called Fran Fine (Drescher) arrives at the house of widowed, and very British, Broadway producer Maxwell Sheffield (Charles Shaughnessy) who mistakenly hires her as the new nanny to look after his three children, Maggie (Nicholle Tom), Grace (Madeline Zima, yes this is why she’s now famous) and Brighton (Benjamin Salisbury). After realizing how much “joie de vivre” she’s bringing to the household, Mr. Sheffield lets Fran stay. Needless to say, from the very first episode we can figure out where the plot will take us. However, this doesn’t take away from the joy that comes from watching Nanny Fine navigate the New York dating scene in a series of stylish, outlandish outfits (the show debuted a whole five years before Sex and the City), deal with aging (Nanny Fine is constantly worried about her biological age and tries to pass as younger) and battle sexism (she often has to prove she is Mr. Sheffield’s equal, even if her intelligence is challenged by those around her).

The show, which risked being cancelled after one season, became a worldwide success, perhaps because it’s also essentially a story about the importance of family, both those we are born into, and the ones we form with friends. The show amassed a truly ridiculous amount of guest stars including people like Marvin Hamlisch, Joan Collins, Bette Midler, Celine Dion, Rosie O’Donnell, Shari Lewis and Lamb Chop, Jason Alexander, Elton John, Jane Seymour and Hollywood screen legend Elizabeth Taylor. James Marsden and Jon Stewart also appeared before most people knew who they were. Overall, it’s a show that constantly kept getting better and trying to win the devotion of its audience.

Fortunately, the entire show was acquired by Shout! Factory, who took on the task of producing the very first DVD release containing the entire series, for the first time fans of the show will be able to relive the misadventures of Fran Fine (Fran Drescher) as The Nanny: The Complete Series arrives in stores on May 2015. The beautiful set includes all 146 episodes of the show, spread over 19 discs that exude pure joy; even the artwork bursts with multiple colors, and Drescher’s iconic grin is printed in each and every one of them. To celebrate the occasion as we should, we have comprised a list of the absolute best episodes of The Nanny, based on rewatchability, the outrageousness of Fran’s Emmy-winning costumes, and memorable lines. Newbies and fans alike should find something of worth among these fine (no pun intended) half hours of television.

10. “First Date” (Season five, Episode two)

Mr. Sheffield decides to take Nanny Fine out on a real date and invites her to come to the screening of Elton John’s new film (the legendary musician appears as himself), only to discover that Nanny Fine was once terribly rude to John. Trying to save face and avoid getting Mr. Sheffield in trouble, Ms. Fine disguises herself as her Grandma Yetta. Hilarity ensues. This episode is a remarkable showcase for Drescher’s chameleonic abilities, especially because she is able to play off Ann Morgan Guilbert’s performance as Yetta. Ray Charles also appears as Yetta’s boyfriend Sammy.

9. “The Nanny and the Hunk Producer” (Season four, Episode 20)

Mr. Sheffield wins the Tony Award for Best Play, but soon finds out that with adoration come the tabloids, who start making up stories about him and Ms. Fine starting an affair when he was still married. Ms. Fine is shocked by the fact that they imply she’s 40 years old. In this episode, the writers poke fun at the entertainment industry’s obsession with youth, with Drescher turning in a nuanced critique of her own casting in the show.

8. “The Honeymoon’s Overboard” (Season six, Episode one)

After Maxwell and Fran go missing on their honeymoon (they fall off their yacht), they wake up in a deserted island, where Fran has to go back to her old ways and look after Maxwell, who has fallen ill. After his recovery, they realize the setting might also induce them to some “hot lovin’”, and they reenact a hilarious version of Blue Lagoon. Two chimpanzees steal the episode in the credits sequence. Frank Sinatra’s “Strangers in the Night” has never been used with such efficiency.

7. “Lamb Chop’s on the Menu” (Season two, Episode 20)

Drescher often kept The Nanny as a family affair, and her beloved Pomeranian, Chester, often appeared playing C.C. Babcock’s (Lauren Lane) dog. In this episode, Chester is at the center of controversy when he devours guest star Lamb Chop, potentially destroying Mr. Sheffield’s budding film career. Beloved children’s icon Shari Lewis steals the show bringing her unique blend of sass and warm humor to a show and has Lamb Chop hit on Mr.Sheffield.

6. “Pen Pal” (Season three, Episode one)

In a plot practically borrowed from an Ernest Lubitsch film, Ms. Fine is exhilarated by the idea of meeting her pen pal Lenny, but is worried because she has created a fantastical life for herself, which will only disappoint him. Three seasons in, this is truly the first episode where we realize Mr. Sheffield is madly in love with Ms. Fine, as he pushes her to go on the date with Lenny only so he will get the last laugh and prove her wrong. The show is notorious for a subplot worthy of its own episode in which C.C. and her frenemy, the butler Niles (Daniel Davis) engage in a sexual charade that hasn’t aged a bit.

5. “Where’s the Pearls” (Season three, Episode 21)

The Nanny often borrowed insane plots from soap operas, and in this episode they recur to good old fashioned amnesia, as Ms. Fine suddenly finds herself believing she’s married to Mr. Sheffield after a taxi accident (Rosie O’Donnell was driving). To make matters worse, at the time of the accident, she was carrying very important cargo: Elizabeth Taylor’s priceless black pearl necklace, which also goes missing.

4. “A Pup in Paris” (Season three, Episode 27)

The third season of the show might very well be its best, partly because it was when the show finally found its voice and realized that it should go all out on it, with each episode being more outrageous than the previous. Similarly, Ms. Fine’s outfits got more elaborate by the scene; in this episode, set mostly in Paris, we see her appear in stunning creations that make her look absolutely irresistible, so much that after a bumpy flight, Mr. Sheffield says “I love you”, only to then take it back. In ’90s television talk, this moment was as significant as Rachel and Ross’ “we were on a break”.

3. “Me and Mrs. Joan” (Season four, Episode six)

Joan Collins guest stars as Mr. Sheffield’s stepmother, a woman he defines as a “tart”, who once used to work for his father. Realizing that she is very much alike to this woman, Ms. Fine decides to use it in order to manipulate Mr. Sheffield. Oedipal issues abound in an episode that also oozes sexuality from Collins.

2. “The Car Show” (Season four, Episode ten)

Fine enters a modeling competition to win a car for Grace, and prove she too can give the children gifts, but in order to win she must first learn how to drive a stick shift car. Mr. Sheffield takes her out for lessons and accidentally sets off a trauma of Vertigo proportions that has Ms. Fine screaming for help. Throughout the show, we learn of Fine’s obsession with Barbra Streisand, and in this episode Babs is used as a perfect placebo. Eve though Babs never appeared on the show, her influence is strong. The last season of the show featured “The Way We Were” in the closing credits.

1. “The Rosie Show” (Season four, Episode four)

Talk about ’90s crossovers! Nanny Fine and her best friend Val (the incomparable Rachel Chagall) attend a taping of The Rosie O’Donnell Show where Fran gets accidentally invited to come back on a weekly basis to give parenting advice. Fame begins to get the best of Fine, and Sheffield, fearful of losing her, decides to employ one of the oldest tricks in the book: he tells her that he dreamt a ghost appeared to him and warned him that terrible things would happen if she stayed on the show. The episode is hilarious from start to finish, but it also deals a lot with the show’s obsession with Broadway, as the dream in question is a parody of a sequence from Fiddler on the Roof, and Rosie’s show was famous during the decade for serving as an entry point for Broadway shows to reach audiences beyond NYC.

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The Nanny is certainly a show that needs to be rediscovered. Shout! Factory’s edition also includes select episode commentary from Drescher, a making-of featurette and newly recorded interviews with Drescher and the executive producers. It’s a must for comedy lovers, but good luck getting the theme song out of your head afterwards.