The Ten Best DREAM ON Episodes of Season Three

Welcome to a new Sitcom Tuesday and the continuation 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.


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, DORIEN WILSON as Eddie Charles, and DENNY DILLON as Toby Pedalbee. MICHAEL McKEAN recurs as Gibby.


Dream On’s third season, its first full year (26 half-hours, spanning six months), comes when the show’s developed high quality shakes figurative hands with its critical favor, representing to the industry all the seemingly limitless opportunities that cable television would be able to provide for unique, creative content in the coming decades. Today, it offers viewers an early example of what a critically acclaimed HBO sitcom looked like when HBO sitcoms were first critically acclaimed. Of course, by all accounts, Dream On was still a niche show in 1992 – a fate that would be sealed when The Larry Sanders Show premiered in the middle of the season and became HBO’s comedic poster child (and even greater success story). But now the Dream On show was spoken about fondly by anyone smart enough to be “in the know.” So, this collection of episodes came when the series was not only able to claim excellence, but also started to enjoy an enhanced popularity. For in addition to recognition by the CableACE Awards, the season also earned Dream On its only two Emmys – Directing and Guest Acting – for an installment that we’ll discuss in a bit. This ascent in acclaim, which presumes itself right from the beginning of the season, also led to a rise in the series’ level of confidence, as the year operates with a gloss and a steadiness indicative of both a bigger budget and a self-assured creative standing, which means more narrative risk-taking. Here in Season Three, these risks are generally episodically successful – there are more turkeys than last season, but no more than we anticipate from a weekly series – for the show still understands that it must engage with its premise-rooted dichotomies of action and gimmick, romance and realism, and heart and heat, to navigate weekly stories that are, with few exceptions, driven by the characters. In utilizing at least one of these elements, and delivering on behalf of its players, almost every episode has something to enjoy. This is one reason the series was critically well-received during this era: a high “batting average” that (spoiler alert) won’t last into the next season, when HBO’s elevated profile means even more attention for Dream On, even though its quality has begun to diminish.


But while Dream On’s third season, the last with full-time involvement from creators Kauffman and Crane, finds success on the micro level (no small feat, mind you), issues of identity on a macro scale, regarding the general direction of the series as a collective entity, begin to arise. You see, when I wrote above about the year’s “batting average,” I was only telling half the story. Yes, because of how each episode is written, there’s something premise-reaffirming to enjoy in nearly every offering here (although, there are some entries, for reasons to be discussed, that just don’t delight like they should, forming clear hierarchies of worth). But this consistency in appeal is not married to a consistency in tone; it’s quite the opposite, actually, as this year finds the show vacillating not merely between the core dynamic responsible for its comedic identity – romance vs. realism – but also between genre-based narrative extensions of this relationship: farcical comedy and hard-hitting drama. Both, of course, are more hyperbolically realized than in the two seasons prior – representing different extremes that go beyond the show’s figurative umbrella, and which are now starting to exist independently of one another. With regard to drama, Season Three is the first that thinks fluctuations in objective are both justified by the show’s presence on the convention-busting cable and made valuable by Kauffman and Crane’s shared belief that heavy, emotional moments are necessary in a character-driven comedy. Surprisingly, although I don’t aesthetically appreciate a comedy series feeling a substantive responsibility to provide more than laughs (as I think such a desire is often an excuse to shirk the most fundamental responsibility to the audience), I agree with the notion that Dream On needs to have darker moments, both because of its position on HBO, and also because of said character aims. In fact, I think it’s beneficial for the comedy in any series when its scripts use motivated drama to present as many sides of the characters as possible.


What I don’t like, and this season only points toward next year’s bigger issues, is the grandiosity with which both genres are allowed to play. Now, I say this as someone who thinks extremes are necessary in entertainment; that is, it’s important to elicit extreme responses in order to be memorable (be they laughter or tears). But as someone who also thinks such drastic tonal variations can hamper a series’ integrity and lead to overarching identity questions, I’m worried – especially because Dream On has always been a balancing act of various tension-battling aesthetics. Hard-hitting and heavy against dreamy, creamy and light. To little surprise, I prefer the funnier outings, for I find humor the basic necessity in all the shows I discuss here. However, there is definitely a line of broadness, of believability, of identity-cohesion, that can be and is crossed – on both sides. For example, a Kauffman-Crane script, “It Came From Beneath The Sink,” crafts an amusing story about Martin being tormented by a mouse, but nearly cartoons the scenario with a ridiculously sized rodent and some unmotivated hysteria. It’s not meritless, but it pushes for gaggy laughs and stretches credulity – so it doesn’t work for this truthful, character-driven series. On the other end of this figurative spectrum are the too-forceful dramas, and for this example, let’s use another Kauffman-Crane script, the Emmy-winning “For Peter’s Sake,” about Martin working with an author dying of AIDS (which, for my musical theatre fans, also guest stars Gwen Verdon). To this season’s and these writers’ credit, it’s not completely laugh-free. But the subject is so lofty that, in spite of the strength of the performances and the sincerity of the material, the entry can’t be enjoyed alongside 90% of the season. That is, it doesn’t play within the established comedic rules of the series – what the audience is supposed to get from Dream On – so it doesn’t work either. These two contrasting installments may have a micro appeal (something individual to enjoy), but not a macro one (based on the show and the sitcom genre). They both represent parts of Dream On’s identity, but neither is ideal, for they each reject premise-required balance in favor of alienating extremes.


The other identity-related dilemma here centers on the core relationship between romance and realism. This season, more than the first two combined, alternates between suggesting the paramount nature of romance (a Kauffman-Crane focus, proven by Friends) and the channel’s unavoidable emphasis on harsh realism. But it often avoids engaging them simultaneously. While the romance is usually reinforced through the Martin/Judith relationship, which in episodes like “For Richard Or For Poorer” or “The Rocky Marriage Picture Show” (neither of which deliver enough laughs) paints their reconciliation as a genuine possibility, the latter is evidenced by more weightily designed entries like “For Peter’s Sake” or “B.S. Elliot,” where the universal human truths are jaded, shaded, and utterly HBO. I think there’s room for all sensibilities within the show’s premise – just keep it character-driven, please. But given the heightened nature of these alternating depictions, identity questions once again, resurface: Is Dream On the deep, serious show covering subject matter that networks won’t touch? Or is Dream On the goofy, guffaw-wanting rom-com that gets to sneak in a little nudity? Now, I don’t think the show should have to choose, but, frankly, we wouldn’t be asking these questions if it could handle both; otherwise, we’d gladly agree that Dream On was all the above and more. However, hewing toward extremes begins to corrupt last year’s achieved balance and pushes the show into picking a lane. So, sadly, it does. The increase in narrative serialization, especially at the end of this year, suggests the eventual triumph of romance over reality, and while grand fluctuations in tone will continue in Season Four, next year sees the former unseat the latter as the more important element, thus disrupting the series’ foundation. But that’s for later. In the meantime, I’ll note the strength of the characterizations this year (more below), and reinforce its consistent entertainment. Although Season Two best reflects the series’ identity, Season Three has the most best episodes. As usual, I have picked ten that I think exemplify the year’s strongest.


Here are my picks for the ten best episodes of Season Three. (They are in AIRING ORDER.) Remember, installments originally aired in hour-long blocks are considered two separate entries.


01) Episode 31: “And Bimbo Was His Name-O (II)” (Aired: 06/06/92)

Martin’s life is turned upside down as a result of his affair with a senate candidate’s wife.

Written by David Crane & Marta Kauffman | Directed by Eric Laneuville


Continuing the trend that began last year, Dream On launches the season with an hour-long excursion featuring big guest stars and larger-than-life plots. This installment — the second half of which I’m highlighting here (although you should watch both parts) — guest stars George Hamilton as a senate candidate and Teri Garr as his wife, who has an affair with Martin that becomes a public scandal (see: Gennifer Flowers and then presidential candidate Bill Clinton). Naturally, such a lofty story means that the episode, which is very self-aware and features highly-promoted cameos by Flowers, Jessica Hahn, and Rita Jenrette, is mostly a Victory in Premise. And while I don’t think this is the type of storytelling Dream On does best — because it has little to do with the characters themselves — the excursion, especially Part II, boasts excellent use of Martin’s thought bubbles, representing an ability to make difficult stories work within the framework of the series’ premise. Also, it’d be hard to deny that this isn’t among the show’s most memorable — and because it has some big laughs, I couldn’t not feature it here.

02) Episode 32: “Nightmare On Bleecker Street” (Aired: 06/13/92)

Toby has nightmares about her killing Martin.

Written by Stephen Engel | Directed by John Landis


A terrific episode for Toby, whose worth was really proven last year in a couple of comedically delightful offerings, this installment is one of several in Season Three that simply solidifies what an asset she is to the show’s sense of humor; at this point, any episode with a generous helping of Toby usually means a funnier outing than those focused on other characters (like Judith and Jeremy). But this entry gets additional credit because, aside from being quite humorous, the well-constructed narrative intersects Toby and Judith (two characters in different realms of Martin’s life), as the former attends a group therapy session with the latter to discuss the nightmares she’s been having about murdering Martin. Also of note, this is the first script by Stephen Engel, who’ll become one of the show’s head writers. (Plus, TV legend Sheldon Leonard guests!)

03) Episode 36: “Bad Girls” (Aired: 07/11/92)

Martin dates the mother of Jeremy’s rebellious girlfriend.

Written by Michael Curtis & Gregory S. Malins | Directed by Betty Thomas


Adrienne Barbeau is the guest star of note here. (Are you noticing a bit of a trend? Dream On, given its creative cachet as artsy and adult, had no shortage of actors clamoring to come in at this point for episodic support.) She plays the “bad mom” of the “bad girl” that Jeremy has been dating — and of whom Martin disapproves, until he starts dating her mama. It’s fun to see Martin take on a more subservient role in a sexual relationship, and the audacity accompanying the characters of both mother and daughter helps to guarantee that big laughs are on the agenda. Also, on a more fundamental level, it’s a relief to get a story utilizing Jeremy that concerns itself with the comedy, for too often the show feels capable of resting on sentiment with him, and despite often justifying it, it’s never something that I prioritize in a sitcom.

04) Episode 37: “Here Comes The Bribe” (Aired: 07/18/92)

Toby agrees to marry Gibby so that he can stay in the country.

Written by Eileen Conn & Andrew Gordon | Directed by Betty Thomas


An office episode predicated on the optimal usage of both Toby and Gibby, the latter played with invigorating smarm by Michael McKean, this outing engages with one of those “typical sitcom” (I use this pejoratively because any show could do the story, indicating a lack of originality) premises that I usually revile — even though classics like Taxi weren’t above engaging with it either. Yet this installment, because of its focus, sets itself up as one of the year’s funniest, and in another case of Dream On expanding its universe with a well-cast soon-to-be-recurring player, introduces Valerie Landsburg as Gina Pedalbee, Toby’s sister. (Just wait until next season when we meet their mom, played by someone now beloved!) So despite the story, the big-laugh character moments make it all worthwhile. Among this season’s most comedic.

05) Episode 38: “May Divorce Be With You” (Aired: 07/25/92)

Martin learns that his parents are planning to divorce.

Written by David Crane & Marta Kauffman | Directed by Bethany Rooney


I have chosen this to represent the season’s MVE (Most Valuable Episode). It wasn’t necessarily an easy choice, because although there are hierarchies of favor that I could form with most of the installments on this list, none really stand out as being undoubtedly superior to the rest. (However, I’d like to reiterate something noted last week: the best episodes here are funnier and more memorable than the best from Season Two, even though that season, for many reasons previously discussed, remains more collectively desirable due to its identity-cohesion.) I give the edge to this episode because, with a script by Crane and Kauffman, who created the series and know their characters best, it’s the year’s strongest example of the show’s ability to balance both romance with realism, and as discussed at length in my introduction, great big laughs with great big drama. (This balance was not achieved in the aforementioned “For Peter’s Sake.”) Both the comedy and the pathos come from the introduction of Martin’s parents, played deliciously over the next few seasons by Renee Taylor and Paul Dooley, two dynamic character actors who will assert themselves as some of the series’ most rewarding guest players for both humor and story. In this episode, Martin’s folks announce their plans for divorce, which naturally sets up a character-centric conflict as Martin has to come to terms with this news, along with the revelation that his mother is seeing someone else. (That’s where the big laughs come into play!)

06) Episode 39: “Come And Knock On Our Door…” (Aired: 08/01/92)

A woman asks Martin and Eddie to join her in a threesome.

Written by Eileen Conn & Andrew Gordon | Directed by John Landis


With Friends just two years away, Season Three of Dream On — again, the last with Kauffman and Crane running the day-to-day operations — offers several knowing glances to the duo’s more successful series, namely guest appearances by two future regulars: Matthew Perry (in an outing highlighted below as an Honorable Mention) and Courteney Cox, who appears here in this offering as a woman to whom both Martin and Eddie are attracted. The series’ reputation as an exceedingly adult enterprise (partly mandated by HBO) is reinforced through the course that the narrative then takes: she asks them to have a threesome with her. They both acquiesce, which then focuses the story onto what this development does to their friendship. It’s a smart, sexy episode — it’s not one of the funniest — but it’s so in-keeping with the identity that both the channel and show are aiming to project that it feels especially premise-connected.

07) Episode 41: “What Women Want” (Aired: 08/15/92)

Martin competes with another woman for his girlfriend’s affections.

Written by Theresa Rebeck | Directed by Bethany Rooney


As with the above, this is an undoubtedly adult, sexy excursion that helps to reinforce the series’ identifiable brand, boasting even better guest talent, some narrative intrigue, and rich laughs. The premise has Martin dating a woman, played by Jessica Lundy, who’s just coming off a relationship with, as it turns out, another woman, played by the ever-amusing (and unlike any other) Jennifer Tilly, whose character is determined to win her ex-girlfrind back. The switch of having Martin compete not with another man, but with another woman, forms the crux of the story’s value, for this is the type of mature play on expectations that Dream On, given its HBO standing, is able to do freely — and indeed must do for its own identity. The novelty of the story doesn’t overwhelm the comedy, however, and in fact, helps boost the whole proceedings.

08) Episode 45: “Theory Of Relativity” (Aired: 09/12/92)

Martin finds himself attracted to his cousin.

Written by Howard J. Morris | Directed by Art Wolff


Given the success of “May Divorce Be With You,” it’s no surprise that this episode was crafted to reuse Renee Taylor, and introduce more of her family — including Sylvia Kauders, Phil Leeds, and Cliff Norton, all of whom we’ll see a few more times, along with Connie Sawyer. Their presences alone help to elevate this installment to, at least, Honorable Mention variety. But what truly allows the episode to earn its worth is the sexual depravity (and still, the odd relatabiltiy) of the premise, as Martin finds himself mutually attracted to his cousin (Helen Slater, who would star in an unsold Kauffman-Crane pilot, Couples, which some call the “pre-Friends“). The mature premise, coupled with both the laughs that come from the detestability of the notion (made rich by the material afforded to the guest stars) and the character-driven humanity that’s never lost, ensures this as a special, notable entry — better than it initially seems.

09) Episode 46: “Up All Night” (Aired: 09/19/92)

Martin and Toby must stay up all night to help an author recreate a manuscript.

Written by Michael Curtis & Gregory S. Malins | Directed by Paul Miller


This installment boasts a unique energy that’s not found anywhere else in the season — a sort of manic claustrophobia that fuels the comedy and is no doubt fostered by the near unity of time and place that this premise, about Martin and Toby trying to help an author (Fred Willard, always a pleasure to see around) recreate his manuscript after it’s been destroyed by a vengeful wife (Valerie Mahaffey, another one who’s always a pleasure to see around). There’s a bit of a madcap, farcical lunacy to the proceedings, but because the action is so tight, I find myself not having trouble with any believability concerns, as the delirious nature of our protagonist seems to keep the happenings, and the way in which they’re presented, motivated. Also, this outing features the annual appearance of the riotous June Gable as determined author Libby Friedman.

10) Episode 47: “The Guilty Party” (Aired: 09/26/92)

Martin throws Eddie a Bachelor Party on the eve of the latter’s wedding.

Written by Jeff Greenstein & Jeff Strauss | Directed by John Axness


Of all the episodes on today’s list, this was the one whose inclusion was the least assured, and this may be somewhat of a surprise, given that it’s notable for a variety of reasons, including guest appearances by John Kassir (of HBO’s 1st And Ten), Dan Martin, and David Hyde Pierce (then in Norman Lear’s The Powers That Be, which was created by Kauffman and Crane and will be discussed in tomorrow’s Wildcard Wednesday). But the episode lacks a certain guiding focus that, while not something I explicitly desire, can sometimes hinder the storytelling if absent. In this case, there are a lot of funny ideas — the stripper getting a cold, Martin’s friends learning that he sexually experimented with another guy — kind of thrown together to create one evening of bachelor party revelry. In the end, it’s the Martin/Eddie dynamic that tightens it.


Other notable episodes that merit mention here include: “For Peter’s Sake,” the beloved Emmy-winning outing that isn’t totally without laughs, but generally doesn’t strike the necessary tonal balance required to appreciate it as a work of situation comedy (nevertheless, I recommend watching it — there are great performances), “Red All Over,” which introduces Eddie’s bride-to-be, “The Son Also Rises,” which has one single scene of excellence — Martin teaching Jeremy how to use a condom — that’s just as funny as it reads, “Domestic Bliss,” notable mostly for the guest appearance of Salma Hayek, “No Deposit, No Return,” which, again, has one single scene of excellence — Martin going to a sperm bank — that makes the entire outing worthwhile, and, lastly, “To The Moon, Alex!,” which is most notable for the guest appearance of Matthew Perry, but is otherwise hinged too much on the guest character and the machinations of the plot.



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

“May Divorce Be With You”




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