The Five Best DREAM ON Episodes of Season One

Welcome to a new Sitcom Tuesday and the start of our series on the best of Dream On (1990-1996, HBO), one of the premium cable network’s earliest and most fondly remembered comedies. As of this publication, only the first two years have been released on DVD.


A divorced editor at a small Manhattan based-publishing house has a unique perspective on life, love, and parenting. Dream On stars BRIAN BENBEN as Martin Tupper, WENDIE MALICK as Judith Tupper Stone, CHRIS DEMETRAL as Jeremy Tupper, JEFF JOSEPH as Eddie Charles, and DENNY DILLON as Toby Pedalbee.


When Dream On premiered on HBO in the summer of 1990, the premium cable channel had only one notable situation comedy to its name – 1st And Ten (1984-1991) – and despite that series’ healthy run, the limited viewership and critical attention paid to HBO in this era kept the show from making a significant impact on the company’s burgeoning brand. It wasn’t until after the 1988 WGA Strike, when audiences turned outward for content they weren’t getting on the script-dependent broadcast networks (sound familiar?), that the time was right for cable to attract a healthy following, allowing for a comedy series that would showcase what non-network television had to offer, while getting to define its style and notions of quality. Over the next six weeks – yes, I will be giving each season of this series its own post, even though a few could be combined to make fuller lists – we’ll be exploring the best episodes from the channel’s first truly successful situation comedy, which I will posit as having helped to determine HBO’s ongoing comedic modus operandi, without actually getting to define our perception of it; that honor would go to the more critically and commercially successful The Larry Sanders Show (1992-1998, HBO), coverage of which will begin immediately after Dream On. As always, we’ll be discussing the show’s strengths and weaknesses, while tracking qualitative changes in its seasonal output. We begin this week with the impetus for its creation: the MCA Universal Library of old cinema and (largely) forgotten television. Looking for a way to make use of this vast collection of media history, which included everything from She Done Him Wrong (1933) to episodes of Schlitz Playhouse Of Stars with folks like Ronald Reagan, director John Landis bought a concept pitched by novice TV scribes Marta Kauffman and David Crane, who would go on with Dream On‘s Kevin S. Bright to create Friends (1994-2004, NBC), scheduled for coverage next year.


Their concept involved using these vintage clips as “thought bubbles” to punctuate the action and reveal the inner workings of the lead character, a divorced book editor living in Manhattan. The idea was genius; while feeding into the trend of televisual literacy and self-awareness of the medium that we’ve been exploring on this blog since last year with It’s Garry Shandling’s Show and Married… With Children, the clips would also serve a motivated purpose in the show: revealing character. But because the series would predicate its premise on the use of pre-existing material, which is a very basic gimmick (simply because it’s not, by itself, character-driven), there are some preliminary guidelines to be discussed regarding how the show best actualizes this part of its concept. I often liken the “thought bubbles” to icing on a cake, adding sweet (comedic) flavor to an already nourishing and substantive dessert: a delicious layer added to a filling, delicious foundation. In other words, a scene can’t be entirely reliant on Martin’s punctuating vintage media thoughts for its comedy – the action must be worthwhile in itself – and the clips can’t be the force that dictates (or completely overshadows) a scene’s purpose, for they themselves need a base of support. As mentioned above, these cutaways work best when they reveal more about Martin than they do about the nature of a specific scenario’s comedy. We should be able to enjoy a moment without a clip, but after seeing one, feel like something meaningful has been added. Ultimately, as with Murphy Brown’s use of politics, although these asides can threaten to distract from where the series needs to be focused (character), they remain an integral part of the show’s identity – and any episode that doesn’t make good use of them is not living up to its promise to the audience. Fortunately, Dream On is generally smart about the way it invokes its premise – again, through character – and the only real concerns are situational.


The use of MCA Universal’s Library of vintage entertainments (and what this suggests about television’s ongoing evolution), along with the apparent inability to keep from showing awareness of both the history and the mechanics of TV, is very apropos for what we now think today about HBO, whose material is marketed as smart television for aware viewers. In this regard, Dream On hits a part of its brand definition target exactly – in the same way that The Larry Sanders Show will do through its television-related premise, affirming the intellect (even if this pertains only to the medium) that the channel will forever aim to project through its identity. And yet, on the subject of identity, we can’t ignore how Dream On simultaneously doesn’t adhere to elements of the HBO brand — elements that we’ll see introduced as early as August in the aforementioned The Larry Sanders Show, specifically the darker and seemingly irreverent sensibilities that feed into the channel’s anti-broadcast network directive. In the case of this series, the incorporation of beautiful black-and-white clips from decades past helps to foster a sense of magnificent romanticism that stands in contrast to the harsher “realism” that HBO comedies, including the series that we’ll be discussing after Dream On, usually proclaim. This sense of sentiment is also fueled by the series’ creators and head writers, Kauffman and Crane, two New York playwrights with little prior experience writing for television. Their most famous work will be the previously mentioned Friends, and it’s interesting to pinpoint the similarities between these two shows. Aside from sharing the same setting, both Friends and Dream On are very concerned with relationships, and from this focus comes a progressive and ever-present emotionality; feelings, unlike on many current HBO comedies, matter – and this will be a major defining point for Dream On, representing a rich conflict, both inside and out.


But this is part of the series’ charm, for its comedy is dependent on the tension that exists between the natural romanticism – coming both from these writers’ and the inherent cinematic/televisual mythos of the “thought bubbles” — and the ever-important sense of realism, that, even by 1990, was a fundamental part of how HBO aimed to market itself, defining its material against the networks’. On Dream On, this taste of reality is exhibited through iconically premium cable offerings – limitless profanity and gratuitous nudity (mostly of Martin’s topless episodic conquests). Yet this is usually shtick, not substance (and something, incidentally, The Larry Sanders Show mostly avoided). Now, in the same way that pre-existing clips can serve as a gimmick, I’m also wary of such “adult” themes, for they too can distract from the construction of comedic material motivated through character. However, the clips themselves – the subject of Dream On’s conception – need the HBO-imposed aesthetics to really leave an impression, and vice versa. For example, Martin being intimate with a character played by Teri Garr is neither amusing nor character-revealing, but Martin being intimate with a character played by Teri Garr while imagining the notorious barge scene from DeMille’s Cleopatra (1934) is both amusing and character-revealing. (This is in reference to the Season Three premiere.) These beats require each other, for the appeal comes from their contrast. Also, because Dream On has an individualized sense of the romantic that doesn’t naturally fit with (and actually sometimes undermines) the channel’s half-cultivated brand, which purports itself as realism-driven, the series is able to stand out and create a comic identity that, in spite (but really because) of the tension, fits on the dissident HBO, helping to increase the company’s creative profile while readying it for the real brand ambassador, The Larry Sanders Show. In future weeks, we’ll explore how Dream On‘s growing imbalance between romance and realism, itself a half-true motif, impacts quality. (If we ever cover Sex And The City, a similar discussion will be had.)


Frankly, Dream On is a show that merits viewing largely because of its style – the juxtaposition of glamour with grit – which is a function of the premise. But, as mentioned above, the show uses its gimmicky construct to remain largely character-driven, and this is a credit to Kauffman and Crane, who will reinforce their commitment to character-centric excellence (and the battle to maintain quality therein) on Friends. In Dream On, character is clearly the show’s prime concern. But, when it comes to the comedy – particularly in this first season, although I fear it will persist throughout the entire run – episodic success is derived mostly on the potency of an idea itself (what I’ve labeled a “Victory in Premise”). This observation isn’t to note that most ideas fail to be motivated and centered around the characters, because the majority are. But the supremacy of certain ideas speaks to a concern that’s never really solved: the inequity of humor as it pertains to the characters. That is, while every regular here has substance and value narratively – well, they will; the first season is all about Martin and the novelty of the premise – they’re never all capable of inspiring stories with a substantial number of laughs. Naturally, the kid (played by Brian Demetral), despite tapping emotional areas for Martin, is not always good for comedy, and Martin’s ex-wife, Judith, played by the funny Wendie Malick, is hit-and-miss (we’ll have more to discuss about her usage in the weeks ahead), while Martin’s secretary Toby (Denny Dillon) and his best friend Eddie (played here by Jeff Joseph, but recast next season with an actor who shares better chemistry with the entire ensemble) are generally hilarious. This will be the case throughout the run and will come to define some of the series’ weaknesses. Here, it’s still too early to say this concretely, as, once again, the first season is all about both our leading man, played with palpable humanity by Brian Benben, and the infectious, creative joy of the concept. Dream On will become funnier and more character-concerned in the years ahead. But, in the meantime, I have picked five episodes that I think exemplify this season’s strongest.


Originally I intended to cover Seasons One and Two together, as they boast a total of 29 episodes. I would have chosen 13 installments, theoretically breaking down as six from the first year and seven from the second. But because Season Two is much stronger than One, I decided to give the second year a slot designed for its predecessor; I figured, because it was the same post, it’d still add up to 13 — there’d be no problem. Then I made the choice to split these entries during drafting, ultimately opting to keep intact this lopsided episode count — five and eight — as this breakdown best represents my thoughts on the two seasons’ finest. So, here are my picks for the five best episodes of Season One. (They are in AIRING ORDER.)


01) Episode 3: “Sex And The Single Father” (Aired: 07/22/90)

Martin lectures Jeremy about sex.

Written by Marta Kauffman & David Crane | Directed by Arlene Sanford


Following two initial episodes that adequately showcase the series’ premise — divorced book editor with a preteen son and lingering feelings for his ex-wife; got it — along with the foundational gimmick of the older clips as the protagonist’s “thought bubbles,” this installment is the first to, quite frankly, bring something comedic to the figurative table. While the show’s use of sex, a function of its HBO-ness, will remain gratuitous for the first half (at least) of its existence, it’s always an important part of the series’ identity — giving something for the show’s romantically tinged sensibilities to juxtapose (as a source of comedy). Also, this offering is notable for introducing Libby Friedman, a recurring character (we’ll see her about once a year) played by the funny June Gable, best known to sitcom fans as Joey’s agent Estelle on Friends. It wasn’t an easy choice, but because of its initial solidification of several elements, it’s my MVE.

02) Episode 5: “Angst For The Memories” (Aired: 08/05/90)

Martin writes a play about his relationship with Judith.

Written by Marta Kauffman & David Crane | Directed by Arlene Sanford


One of the things that will become fodder for more in-depth discussion in the weeks ahead is the show’s treatment of the relationship between Martin and his ex-wife. Kauffman and Crane, not surprisingly, really play up the depth of feeling that exists between the two characters — right from the pilot — and these early seasons, in spite of possessing no narrative desire to reconcile them (which will eventually happen — we’ll, of course, discuss), clearly makes that a possibility. Now, I’ve already mentioned how I find Judith (and Jeremy) comedically lesser presences than the rest of the cast, so the key in their episodes is to keep the action entirely character-driven, and not governed by any unwieldy sentiment or serialized goals. In the case of this offering, it merits mention because it’s actually funny; the musical sequence is a standout.

03) Episode 10: “Trojan War” (Aired: 09/09/90)

Nina encourages Martin to get tested for AIDS.

Written by Dava Savel | Directed by Betty Thomas


This is the second of three episodes that we’ll refer to as the “Nina Trilogy,” as they’re narratively concerned with the romance that develops between Martin and a woman in his building, Nina (Julie Carmen), whom he meets, in the offering prior, in the laundry room. Although her three outings are generally well-liked, by these first year standards, I think they inevitably contend with more story points than character beats, and with this installment as the exception, they’re not as comedic as they need be. Fortunately, this outing is indeed the exception, for the subject matter is inherently comedic — just imagine Martin having to go to the clinic and get tested for STDs  (there are some great laughs here) and the script actualizes the tension between fantasy and reality within the narrative: the glamour/griminess of sex.

04) Episode 13: “Doing The Bossa Nova” (Aired: 09/30/90)

Martin has an affair with his new boss.

Written by Jeff Greenstein & Jeff Strauss | Directed by Arlene Sanford


Although the office will really become a setting for comedic excellence in the following season, when the show introduces Michael McKean as Martin’s boss, Gibby Fiske, this prescient episode illustrates why it was such a smart decision to enhance the career aspects of Martin’s life — it’s a terrific source for both story and laughs — and regardless of McKean’s presence, we would have certainly seen more of the office anyway. Not only does this setting allow more time for the irascible Toby, who gets considerable play and development over the next two seasons (yet already shows her comedic potential here), but the seemingly glamorous world of publishing is just ripe for the dose of harsh reality that HBO is so eager to apply; thus, the series’ premise is truly invoked. Also, this episode is the first with the recurring Vernon Factor (Lou DiMaggio).

05) Episode 14: “Premarital Ex” (Aired: 10/07/90)

Judith turns to Martin on the eve of her wedding to the perfect Richard Stone.

Written by Marta Kauffman & David Crane | Directed by Arlene Sanford


In complete transparency, there were really only four episodes that asserted the necessity of their inclusions on this list; those were the four above. This installment got bumped up so that I could at least have five episodes to highlight for this season, and my rationale is that, although this is the least amusing entry on today’s list and it does flirt with the light serialization that may prove problematic in years ahead (stay tuned), the outing is important for three specific reasons. One, it’s the place to which the year has been building and reveals where Kauffman and Crane find their heart: the relationship between Martin and Judith. Two, this installment allows Martin and Judith to become closer over the next few seasons (despite the divorce). And three, it’s the “road map” that reveals where the series will “wind up,” such that there are few surprises…


Other notable episodes that merit mention here include: “Death Takes A Coffee Break,” in which Martin dates a 20-year-old, and “… And Sheep Are Nervous,” in which Martin dates a seemingly perfect woman. 



*** The MVE Award for the Best Episode from Season One of Dream On goes to…

“Sex And The Single Father”




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

2 thoughts on “The Five Best DREAM ON Episodes of Season One

  1. Just reading this post brought back memories for me. I need to dig out my S1&2 dvd set which I bought 10+ years ago when it was first released. I don’t think I watched HBO until a few seasons in – probably around LARRY SANDERS’ start. Really unique for what was being produced at the time, and I guess I just ignored the Kauffman/Crane FRIENDS connections. Will have to watch for an eye towards similarities.

    Thanks for covering this rare show. I know it’s not as popular as SEINFELD or THE GOLDEN GIRLS. But it too deserves to be enjoyed and celebrated.

    • Hi, Elaine! Thanks for reading and commenting.

      I’m very glad to be covering DREAM ON and I hope you’ll stay tuned for these next five weeks!

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