The Eight Best DREAM ON Episodes of Season Two

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.


Crafting coverage for the second season of a successful series is one of my most challenging Sitcom Tuesday endeavors, for despite many contemporary myths regarding the “sophomore slump” (born from the current need to be an immediate runaway hit), the second year of a proven solid situation comedy is not only often better than its predecessor – it’s also routinely the best, representing the moment when a show’s wisdom meets its novelty. (We’ve seen this before – most recently with Murphy Brown and The Golden Girls.) Previously, my knowledge of Dream On has been mostly confined to these first two seasons, the only ones commercially available on DVD, making it difficult to contextualize this year and its quality within the scope of the entire run. But now that I’ve studied the series for this survey, I find that in accordance with the aforementioned trend, Dream On’s second season can probably be deemed – with few counterarguments presented (from my end, anyway) – the best of the entire six, offering viewers the purest and most effective examination of its established identity, a high episodic success rate (read: very few misses), and a sense of purpose directly correlated to the exploration of the show’s premise. This all comes, of course, from guidance by the series’ creators, Marta Kauffman and David Crane, who went on to find even greater success with Friends, a staple of NBC’s Must See TV Thursday line-up in the ‘90s and still one of the genre’s most impactful offerings. (I’ll plug the show again: my thoughts on the best of Friends are due here next summer.) Now, because greatness is easier to show than to tell, my commentary here seems far less essential than the material being highlighted – even more than usual. But, frankly, this is as it should always be – so let’s just discuss the season, with brevity, and get to the list.


After a first year that reveled in its evocative use of old MCA Universal film and television clips – the gimmick upon which the premise is founded – and proved its narrative chops by using this conceit to explore the protagonist, Martin (Brian Benben), Season Two knows the show better than the year before did (naturally and unsurprisingly). This cultivated understanding is vital, and from identity-based knowledge stems the freedom to explore the hero’s universe in ways that further develop all the characters in the ensemble (even those less conducive to hilarity), while still maintaining the delicate tension that exists between romance and realism (or glamor and grit), which I posited last week as being Dream On’s thesis and the crux of its appeal – both as an HBO entity and one that doesn’t adhere to the brand that will be better reinforced by The Larry Sanders Show (coming in August). How can we tell it’s working? Because there are only one or two episodic exceptions that don’t hit the premise’s mark. (You’ll see some fine examples of premise-hitting below.) But real evidence for Season Two’s mastery comes in the years ahead, for although the show will significantly enhance its comedic prospects over the next few weeks – in fact, the funniest episodes are, mostly, still to come – later years are nevertheless saddled with installments that endure damage due to tonal imbalances, either within the stories or the storytelling. Season Two, in contrast, is the most solid of the run, and while I can’t claim the year possesses the greatest number of comedic outings (which is usually one of the most powerful indicators of seasonal supremacy – having a high volume of classics), it’s both infinitely funnier than its predecessor, and can boast the fewest meaningful failures. Truly, never again will the show be so consistently appealing – narratively, I mean – as the upcoming years’ bigger laughs reside in tandem with less favorable developments.


Ultimately, when we mention Dream On’s premise-hitting, heightened understanding, we’re celebrating the way characters are utilized; the show is now better written – and even funnier than before – because Season Two inherently has a better grasp of its players. Furthermore, we’re still dealing with novelty: the characters are fresh and malleable enough – while relatable, based in some valuable Kauffman and Crane truth – that it requires little force to have them motivate humorously conceived and premise-designed stories. You might say that Season Two, like so many others, is lucky because it’s situationally ideal – the writers have learned valuable lessons from the first year and are therefore making fewer mistakes, but still remain unencumbered by narrative-driven shackles that hinder the characters and make believable stories more difficult. Yet I don’t want to rob the second season of its unique charms – most of which involve the characters. In general terms, everyone gets well explored here – not just Martin, but everyone from the comedically reliable Toby to Martin’s immediate family, Jeremy and Judith, who still aren’t positioned for the laughs we’d like, but earn legitimate relevance and appreciation due to the strength of their burgeoning emotional bonds with the protagonist. (Also, they’re not dragging down episodes; the season can easily accept offerings centered around them, because Martin – at this point – benefits from their existence.) Meanwhile, the decision to recast Martin’s best friend Eddie with Dorien Wilson turns an essential role adequately filled last season into an essential role wonderfully filled this season – making for another rich relationship with a lengthy, relatable history. Additionally, the introduction of the recurring Michael McKean as Gibby Fiske, Martin’s new perverted, tyrannical, and eccentric boss cements the workplace as a setting for amusing new stories, further suggesting limitless opportunities – all of which help distinguish Season Two as a uniquely joyful time in the series’ life. So, I have picked eight episodes that I think exemplify this season’s strongest.


Originally I intended to cover Seasons One and Two together, as they boast a combined 29 episodes. I would have chosen a total of 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 the breakdown best represents my thoughts on the two seasons’ finest. So, here are my picks for the eight best episodes of Season Two. (They are in AIRING ORDER.)


01) Episode 16: “The Second Greatest Story Ever Told (II)” (Aired: 07/07/91)

Richard Stone’s life is adapted into a major motion picture.

Written by Marta Kauffman & David Crane | Directed by John Landis


After having explained my reasoning for making this a list of eight episodes, I also must confess that I was really torn about whether to simply keep this entry at seven… but if I did that, it would have meant axing this installment, for it’s the one about which my feelings are the least straghtforward. Frankly, I only wanted to discuss it because it’s the second half of a very popular installment that originally ran on HBO in an hour block (thus, if you watch this entry, you have to see its predecessor) and features guest appearances by Tom Berenger, Mimi Rogers, and David Bowie, along with cameos by Yvonne De Carlo, Eva Gabor, Sylvester Stallone, and Ricardo Montalban. (Stephen Furst, Martin Ferrero, and Fran Drescher also guest — it’s, obviously, a grand affair!) Yes, it’s also gimmicky, and yes, it’s overblown too; but it simply delivers its laughs, and more importantly, doubles down on the self-reflective metatheatricality that, if it’s not directly Dream On‘s aesthetic, is certainly HBO’s. The next three seasons will open with similarly hyperbolic, camp-infused wink-heavy installments, but none will work as well.

02) Episode 19: “Calling The Kettle Black” (Aired: 07/28/91)

Martin and Eddie smoke a joint found in Jeremy’s room.

Written by Jeff Greenstein & Jeff Strauss | Directed by Peter Baldwin


When I first saw this installment — another well-liked entry among the show’s niche’d fan base — years ago upon receiving the DVD set, I was nonplussed: it’s a morality tale with a gimmicky sequence in which Martin and Eddie do the predictable thing (this is HBO) and smoke Jeremy’s joint. That’s it — one single funny idea on which the whole episode rests its merit. But, in this chronological study of the series, I’ve cultivated a more sincere appreciation, recognizing the necessity of the sequence in the building of the Martin/Eddie friendship (which had to be rebooted when Wilson stepped into the role) and delighting in what the offering says about all the characters — particularly the three males. Also, once I’ve gotten over my aversion to the gimmick itself, I really appreciate the strength of the comedy; it’s genuinely funny.

03) Episode 20: “Futile Attraction” (Aired: 08/04/91)

Martin seeks help from a sex therapist and dates one of Judith’s patients.

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


This episode surprises in several ways, as there are a handful of individual hooks notable enough that one might assume they’d simply carry the entire narrative. Yet that turns out not to be the case. Martin’s impotency — a strong story in itself, hitting the heart of HBO’s weekly sex mandate — isn’t the meat of the story; it’s merely the reason for him to see a shrink, played by Martin Mull. But Mull’s guest appearance isn’t the hook, either. What this offering finally ends up being is a story about Martin unknowingly dating one of Judith’s patients (that’s another good narrative that could be strong enough on its own, but isn’t used as such), played by Gina Hecht, who is psychotically violent after intercourse. This is the episode’s core and despite being broad, it’s nevertheless amusing, with a lot to comedically offer along the way.

04) Episode 22: “What I Did For Lust” (Aired: 08/18/91)

Martin falls for a writer whose manuscript he finds repulsive.

Written by Theresa Rebeck | Directed by Bethany Rooney


Michael McKean makes his second appearance in this offering as Gibby Fiske, Martin’s bizarrely sadistic boss, who orders our hero to work on a book by an author (Corinne Bohrer) with whom Martin is being intimate, but whose work he absolutely hates. It’s a simple, direct premise — perfect for Martin, pitting him between sex and personal integrity. Not surprisingly, the script is able to deliver the accompanying laughs with seemingly little effort, and for the most part, they’re character-driven. There are plenty of little moments to appreciate here, as anytime the script concerns itself with the contents of the book, it’s amusing. However, I do think that this is a Victory in Premise, and in spite of my usual objections over this convenient design, the way the characters (both regular and guest) are used here elevates the installment for inclusion.

05) Episode 26: “The Charlotte Letter” (Aired: 09/15/91)

Martin learns his new girlfriend is a former porn star.

Written by Tom Leopold | Directed by Peter Baldwin


Debra Engle, best known to readers of this blog as Blanche’s daughter Rebecca (the second one) on The Golden Girls, plays Martin’s love interest of the week, who he discovers used to be a porn star. It seems like another Victory in Premise, crafted, in his only script for this series, by Tom Leopold (Seinfeld, Cheers, Ellen, Caroline In The City). But, once again, this installment proves to be so much more than that, with a laugh-a-minute teleplay that services the characters well and makes time for truly hysterical stuff — this is another entry with a lot of little moments. My favorite scene, one of the year’s funniest, has Ray Walston as a preacher (Saint Auggie) whose writing style is reminiscent of Raymond Chandler’s (and whose advice to Martin is the same). Meanwhile, there’s great banter between Martin and Eddie, a wonderful comedic climax, and some of the best usage of clips we’ve seen this entire season. The general strength of all these highlighted outings didn’t make this an easy choice, but “The Charlotte Letter” is my MVE.

06) Episode 27: “The Name Of The Game Is Five-Card Stud” (Aired: 09/22/91)

Martin and his co-workers play a game of high stakes poker with the boss.

Written by Theresa Rebeck | Directed by Rob Thompson


The appeal of this installment is its theatricality (which, in the cable era, just beginning at the time of Dream On, is a subversive design) — the majority of the action takes place in Martin’s apartment around the poker table, where he, Toby, and some of his colleagues are embroiled in a game against the boss, Gibby, that’s exceptionally high stakes (and leads to some requisite HBO nudity). I’m always a little wary of sitcom episodes centered around games, because their constructs are so rigid that it’s sometimes hard to find time for character within the narrative mechanics. But the episode’s simplistic design means that we’re exploring the dynamic between Martin and the other folks in his office, particularly Gibby, of whom we see more in this episode than during the rest of the season. And at any rate, it’s conceptually a standout.

07) Episode 28: “So Funny I Forgot To Laugh” [a.k.a. “Stop It, You’re Killing Me”] (Aired: 09/29/91)

Martin’s new girlfriend uses him for material in her stand-up set.

Written by Jeff Greenstein & Jeff Strauss | Directed by Betty Thomas


Not surprisingly, there are quite a few Friends connections within the first three (Kauffman and Crane) seasons of Dream On, and this episode offers another in the form of Maggie Wheeler, best known as Chandler Bing’s on-again/off-again girlfriend with the distinctive voice, Janice. Here she’s far less a caricature, playing Martin’s friend-turned-girlfriend, an aspiring stand-up comedienne who finds success talking about her new beau in the act, with which Martin has a problem. There are plenty of laughs in this outing, but its prime strength is the easy chemistry shared by Benben and Wheeler, a talented comic actress who was always on the cusp of big success and never found it. Also, there’s a real New York feel to this offering that’s only intermittently felt throughout the series, making it another aesthetic standout. A favorite.

08) Episode 29: “Toby Or Not Toby” (Aired: 10/06/91)

Toby and Martin attend (and get drunk at) his aunt’s wake.

Written by Elaine Aronson | Directed by Bethany Rooney


As the season finale, this outing, written by Elaine Aronson (It’s Garry Shandling’s Show, Night Court, Cybill, Roseanne), is one I’ve never heard discussed as being among the series’ best, which surprises me considering that it features guest appearances by Mindy Cohn, Ja’net Dubois, Jane Kean, Larry Linville, Pat Paulsen, Lionel Stander, and Ronald Reagan, Jr. — all playing members of Martin’s family. (This is before we meet his well-cast parents; stay tuned…) There’s plenty to enjoy with all these memorable players — and the wake sequence is one sustaining delight — but I’m really drawn to this episode for the exposure given to Toby. (This is the second entry here where she shines — the other, which is oddly and undeservedly more popular, is an Honorable Mention.) Also, there’s exploration of her relationship with Martin, which, interestingly, almost combusts into something romantic — and then fortunately, doesn’t.


Other notable episodes that merit mention here include: “The 37-Year-Itch,” a sweet entry for Toby that guest stars Dan Castellaneta and features a cute musical number, “No, I’m Just Happy To See You,” which is noticeably well-plotted, and “To Have And Have And Have And Have Not,” which benefits from the sense of history provided to the regular characters. Also, the other half of the hour-long season premiere is a de facto Honorable Mention!



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

“The Charlotte Letter”




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