The Ten Best LIVING SINGLE Episodes of Season Three

Welcome to a new Sitcom Tuesday! This week, we’re continuing our coverage on the best of Living Single (1993-1998, FOX), which is currently available on DVD and HBO Max.

Starring QUEEN LATIFAH as Khadijah, KIM FIELDS as Regine, KIM COLES as Synclaire, ERIKA ALEXANDER as Max, JOHN HENTON as Overton, and T.C. CARSON as Kyle.

Season Three has a handful of memorable episodes relative to the series’ baseline, but it’s a qualitative comedown overall because there are more gimmicks (particularly casting stunts that have nothing to do with the “situation”), and its plotting is even more stagnant as far as these leads and their relationships are concerned. That is, they still don’t motivate story as much as their well-crafted personas should, so they don’t evolve like we expect of regulars on rom-coms, where emotional change (or an acknowledged lack thereof) is an implicit condition of pursuing love in ongoing narrative structures. Again, this deficiency is both due to — and ends up with — the leads not driving action, and plots instead being more detached: a little more generic, a little more gimmicky. That’s why the relationship-led arcs that we do have also fail to connect, and not even the solid Synclaire/Overton bond is well-explored this year — they’re just treading water until an unimaginative May Sweeps proposal… Three’s biggest disappointment, however, is its failure to mine all the dramatic and comedic possibilities suggested by its official coupling of antagonistic lovers Kyle and Max, whose romance was teased in Season One and then ignored for most of Two. Now that they’re paired, we should look forward to stories that have fun juxtaposing their brilliantly conceived personas, enabling them, frankly, to evolve as a result of their pairing (or not evolve, if that’s the point)… like Sam/Diane, Ross/Rachel, etc. Sadly, it seems as if this show is unable or unwilling to conceive ideas directly for them, as they essentially get sidelined again until their February Sweeps breakup… which on one hand comes out of nowhere, but on the other hand feels like it could have existed at any point during this arc, for there’s been little dramatic continuity. This is a shame, for I reiterate: these characters are too well-defined to not be better involved in story — especially in story like this, which is ideally connected to the series’ “Singles in the City” premise — and, even worse, they’re now becoming less realistic because of this strained usage… And yet, if those are macro concerns, Living Single is always written well enough to remain basically good on the micro level — with a consistent episodic quality, and few outright duds. It’s just that Season Three constantly reminds us of why this enjoyable show can’t quite clear the hurdle to overarching greatness.


01) Episode 55: “Come Back Little Diva” (Aired: 08/31/95)

Regine throws a housewarming party; Kyle and Max adjust to their new relationship.

Written by Yvette Lee Bowser | Directed by Ellen Gittelsohn

Season Three’s premiere must follow through on Two’s cliffhanger, with Regine moving out of the apartment after a fight with Khadijah. Ordinarily, I wouldn’t enjoy this contrived narrative notion, for we expect it to be short-lived and therefore inherently irrelevant to character. However, because Living Single generally has a problem with how its leads motivate story, I appreciate that this little arc is hinged on the differences between Regine and Khadijah, whose oppositional personalities inform and help drive the conflict. Accordingly, this feels like a decent usage of them within narrative, even though the narrative itself is unideal… What’s more, any concerns about this story are allayed by the script (the last credited to series creator Yvette Lee Bowser), which is not only comedically sharp — the opening laundromat scene is among this series’ finest — it also knows to sufficiently wrap up this arc, buyably and with enough laughs that flatter the characters. Additionally, I also appreciate this installment for its subplot, which directly acknowledges Max and Kyle’s new relationship — one of only a few stories this year that actually seeks to explore how their dynamic changes as a result of their coupling. Thus, this is a smart show that does what this series is supposed to do with its regulars, and for that reason, it’s my choice for this year’s MVE (Most Valuable Episode). There’s no other segment that I think handles its leads in story as well… and with plenty of big hahas to boot. (The amusing Chip Fields appears in her recurring role of Regine’s mother.)

02) Episode 58: “Grumpy Old Man” (Aired: 09/21/95)

Kyle is depressed about turning thirty.

Written by Becky Hartman Edwards | Directed by Henry Chan

This underrated outing is perhaps the best display of the Kyle/Max relationship as it exists in Season Three, for we get a clear understanding of their romantic rapport when he is depressed about turning thirty and she continues to harass him about it, until a wonderful final scene (again, in the laundromat) where she shakes him out of his funk by showing him what really matters. If there’s any entry here that advocates for their pairing (like previous seasons used to do), it’s this one. Also, I think Kyle’s reaction to growing up is very in-keeping with the Gen X ideal of sustained youth that permeates this era’s “Singles in the City” series, and unlike some other sitcoms with this similar plot, Living Single delivers it particularly funny and believably — and I don’t say that often, for remember, this show’s problems with story tend to hinder the dimensionality and honesty of its characters. So, this is a welcome outlier.

03) Episode 59: “Rags To Riches” (Aired: 09/28/95)

Regine gets a job at a discount store; Overton has a doppelgänger.

Written by Jim Pond & Bill Fuller | Directed by Rae Kraus

There are two fun ideas here in this installment — with its A-story having the most relevance for character, as Regine inadvertently lands a job at a discount store, making her incredibly miserable as she’s now forced to deal with products and a clientele that she feels are beneath her. That’s, as usual, not exactly driven by her own choices, but it’s comical because of what we know about her personality. Additionally, this development is used as the springboard for getting her a new job — as the wardrobe mistress of a soap opera: a career that flatters her ego and opens her up for different types of stories. (This is smart, although it’s too bad we won’t again see John O’Hurley — better known as Seinfeld’s J. Peterman!) Meanwhile, this subplot finds the group discovering a porn star who looks just like Overton… a one-joke gag that allows for many easy one-liners. (It’s a notion Friends would employ several year later, but with more support from its “situation” — a recurring character.) Also, Chip Fields appears again.

04) Episode 60: “The James Bond” (Aired: 10/05/95)

Khadijah and Synclaire disagree over money, while Kyle is jealous over Max’s black book.

Written by Warren Hutcherson | Directed by Leonard R. Garner, Jr.

Another excursion that seems to be underrated, “The James Bond” contains two stories that actually put regulars in conflict, yielding comedy based on their contrasting, or in one case, too-alike, characterizations. The A-story involves a windfall afforded to both Khadijah and Synclaire, and a disagreement over how to spend the money — Khadijah, true to her definition, wants to buy something for her business, while Synclaire, true to her definition, wants to take an acting course. These contrasting ideas speak precisely to who each character is, and there’s an insightful takeaway at the end, with Khadijah and Synclaire talking about the latter’s increased assertiveness. Meanwhile, the subplot is among this year’s best Kyle/Max showcases, as Kyle is jealous that Maxine has one more entry in her black book than he does in his. This is a great B-story because it emphasizes their equally competitive natures — a trait that makes them both compatible and incompatible. (The recurring Shaun Baker appears.)

05) Episode 65: “Mommy Not Dearest” (Aired: 11/16/95)

Max’s mother visits; Khadijah seeks to return a lost wallet.

Written by Becky Hartman Edwards | Directed by Ellen Gittelsohn

CCH Pounder guest stars in this episode as Max’s emotionally distant mother — a character whose very presence, just as we saw with Regine’s and Khadijah’s moms back in Season One, adds to our understanding of her “daughter,” for parents are so intrinsically linked with “growing up” and therefore a “backstory” that they help give a sense of history to whatever principal they’re there to support. That’s exactly what happens in this outing and why I highlight it, for meeting Max’s mother helps make Max a more believable, fully rounded character… and this is needed because, while funny, she can sometimes feel like the most caricatured of the group. As for the subplot, it’s a chance to bank some gaudy guest star cameos (by Burt Ward and Dean Cain) — and if it was the focus of this offering, I wouldn’t be featuring it here.

06) Episode 67: “Let It Snow, Let It Snow, Let It Snow… Dammit” (Aired: 12/14/95)

Overton takes the group up to his family’s remote Canadian cabin for Christmas.

Written by Jim Pond & Bill Fuller | Directed by Rae Kraus

The only other outing here that I also considered for MVE, this is one of the year’s best ensemble shows, because it transplants the entire cast — plus Regine’s date — to Overton’s family’s Canadian cabin for Christmas, and putting all the regulars in close proximity is always fun, for it enables the simple juxtaposition of well-defined leads bouncing off each other. In terms of story, there’s a routine idea where Regine’s beau finds more kinship with Khadijah rather than her, but the real joy comes from the running gag of Overton and Synclaire getting in trouble with the ranger, and the turnaround for Kyle and Max, both of whom are invigorated by this setting and become romantic — a hilarious reversal of expectations, predicated on our awareness of their usual behavior. So, there’s a lot of good stuff here, validating the “hangout” aspect of the series’ premise. (Michael Boatman and Dorian Gregory guest.)

07) Episode 70: “Likes Father, Likes Son” (Aired: 02/01/96)

Regine unknowingly dates both a father and his son.

Written by Daniel Margosis & Robert Horn | Directed by Ellen Gittelsohn

With an inherently comedic logline about Regine unknowingly dating both a father and his son — played by real-life duo Mario and Melvin Van Peebles — this installment is naturally poised to be a riot, not just because of this amusing idea, but also because it’s centered around Regine, the only character for whom this story could work (especially at this point in the season, when Max is still ostensibly with Kyle, although not for long — their breakup episode originally aired on the same evening). Meanwhile, this script relishes in spitting out many jokes related to its comical A-story, and while it’s perhaps a little more circumstantial than I’d like, I can’t deny that it’s laugh-out-loud funny too. In fact, this is one of those half hours that I would miss if I didn’t include it on my list, simply due to its sheer comic memorability.

08) Episode 72: “Tibby Or Not Tibby” (Aired: 02/08/96)

Overton’s uncle doesn’t approve of Synclaire; Kyle and Max deal with their fresh breakup.

Written by Kriss Turner | Directed by Henry Chan

J. Anthony Brown plays Overton’s respected Uncle Tibby in this solid offering that takes a typical sitcom idea and plays with it unexpectedly, for heretofore Synclaire and Overton’s relationship has been smooth sailing, since they’re so obviously compatible (and have such great chemistry). So, to see a guest character — someone who has history with Overton and matters to him a lot — finding fault with Synclaire is an unexpected surprise, for while we typically only get this on shows with couples who are genuinely more of a mismatch, it’s exciting to watch someone as likable and well-intentioned as Synclaire have to justify herself for a change. It’s a position she’s not normally in… Additionally, I really appreciate the subplot, which provides some rare — and belated — continuity to the Kyle/Max arc, addressing their breakup in a way that is probably most meant to establish these characters’ new “status quo.”

09) Episode 76: “Woman To Woman” (Aired: 03/21/96)

Max learns that her college friend is a lesbian and about to marry a woman.

Written by Jim Pond & Bill Fuller | Directed by Rae Kraus

Among this season’s most popular outings, “Woman To Woman” reminds me of a classic Golden Girls segment — “Isn’t It Romantic?” — where Dorothy’s old friend reveals that not only is she a lesbian, but she also has a crush on Rose. It’s a beloved entry, thanks to the sensitivity exhibited by the characters regarding their guest’s sexual orientation — a sign of that series’ trademark Lear-ian liberalism, and how its specific era sought to display it. Living Single — a decade later — reacts similarly, but with more willingness to be potentially insensitive for comedy, as the conflict becomes even more personal when Max is upset to learn that her best friend both hid her sexuality (only from Max), and also that she had a huge crush on Max the whole time — an act of simultaneous duplicity and intimacy that complicates Max’s understanding of her friend. It’s an interesting idea — again, very “Singles in the City” to deal with crushes and orientation — and it’s another show that allows Max to not be as cartoony as she sometimes seems, compared to others. (Karen Malina White and Merrin Dungey appear.)

10) Episode 80: “Compromising Positions” (Aired: 05/09/96)

Regine’s mother catches her having sex; Overton plans to propose to Synclaire.

Written by Warren Hutcherson | Directed by Gil Junger

Season Three’s penultimate showing sets up the year’s finale, which contains a lot of big events that sort of overshadow both the characters and the comedy. I much prefer this installment, which follows Overton’s desire to propose to Synclaire, offering a story where he tries to get her the perfect ring — a goal that takes him to the apartment of an old widower (played by Jack Carter). It’s a funny, but gentle, and ultimately well-written storyline, with Overton in pursuit of a relatable objective that flatters the series’ rom-com identity. Its subplot is similarly premise-validating, as Regine’s hilarious visiting mother (Chip Fields) catches her having sex on the roof with her latest boyfriend — another classic “Singles in the City” idea from this era that yields the expected laughs and helps make this a winning display of Living Single’s charms.


Other notable episodes that merit mention include: “Glass Ceiling,” which has a dull and unideal A-story but a great guest appearance by Dorien Wilson and a fun B-story where Regine’s painter beau is going to render a nude portrait of Max, and “Whatever Happened To Baby Sister,” which reveals more about Khadijah and boasts continuity for Kyle and Max’s breakup. I’ll also cite several outings that are popular because of their gimmicks — “On The Rebound,” in which Khadijah dates Grant Hill, “He Works Hard For The Money,” in which Kyle becomes the escort of a famous actress played by Eartha Kitt, “The Following Is Not A Sponsored Program,” in which the group TLC appears in a dream, and “A Raze In Harlem,” which has 1920s fantasy scenes that allow T.C. Carson to sing again. Lastly, I’ll single out “Baby, I’m Back… Again,” for its Regine subplot, “Wake Up To The Breakup,” which contains Max and Kyle’s split in a well-written scene, ending an arc that otherwise wasn’t, and “Shrink To Fit,” merely for the comic notion of Overton’s clown fear.


*** The MVE Award for the Best Episode from Season Three of Living Single goes to…

“Come Back Little Diva”



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

2 thoughts on “The Ten Best LIVING SINGLE Episodes of Season Three

  1. Another one of my fav seasons. The James Bond is definitely among my top 5 as it shows development in Synclaire and Khadijah. I even like Tibby Or Not Tibby for the scene when Overton threw his uncle out.

    I can’t wait for next week. Two of my favorite episodes appear there.

    • Hi, Track! Thanks for reading and commenting.

      I think LIVING SINGLE’s quality continues to erode as its shortcomings become more evident – so much so that this season isn’t preferrable to me compared to the first two – but I appreciate Three’s fairly consistent quality (relative to its own output) and I share your enthusiasm for the enjoyable entries here.

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