The Five Best DREAM ON Episodes of Season Five

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.


As Friends was gearing up for production in the summer of ’94, the fifth season of Dream On took several collateral hits. In addition to the formal departure of co-creators Marta Kauffman and David Crane, who’d stepped back the previous year to be “Creative Consultants,” Dream On lost Executive Producer Kevin S. Bright when he joined the former duo to create the trio that would turn NBC’s new Thursday night comedy into a cultural touchstone. Also leaving at this time for Friends were Season Four’s head writers, Jeff Greenstein and Jeff Strauss, the only other pair who’d been around since Season One. This left third year addition Stephen Engel to assume their responsibilities while leading an entirely new-to-the-series staff of writers, who, naturally, had different strengths and weaknesses. The group included (but was not limited to) funny scribes like Tom Maxwell and Don Woodard (Just Shoot Me!), Bill Prady (co-creator of The Big Bang Theory), and Victor Levin (Mad About You). Now, although I can’t quite claim that Season Five is better than Four, this collection of episodes doesn’t fail like you might anticipate based on prior trends we saw developing – specifically the choice to give romance more play than realism. This does continue, but it’s balanced by a healthy, consistent sense of humor – better than ever. However, before we discuss some of the creative differences that mark Dream On’s fifth year, let’s be honest about the primary reason it can indulge these unfavorable developments and still delight: there are only 13 total half-hours, the shortest lot of the entire run, meaning fewer chances for duds. This truncation was partly due, I suspect, to HBO’s not wanting to compete with the upcoming syndication deal, which would finally begin on FOX in January 1995. Over those next several months, approximately 20 semi-sanitized episodes of Dream On would air – chopped up for censors and ads (but only the premiere employed canned laughter). This endeavor was a relative failure and most likely contributed to Dream On‘s forthcoming demise, as the series’ future on HBO was dependent on this syndication.


Expectations for Dream On’s FOX life were high (the show had forever shot cleaner variations for future off-HBO airings), and this entire year functions with the implicit belief that it’ll have a life beyond the bounds of the supposedly boundless HBO. In fact, most of the creative tweaks apparent here seem to involve the rejection of the more HBO-inspired elements in favor of fare that could play anywhere. Beyond a reduction in both the show’s nudity and its general salacity (from now on, attempts to invoke the risqué parts of the premise will mostly feel calculated and gratuitous as opposed to creatively important), the year expands upon some of the developments from years past – namely, both the broadening of its sense of humor, such that big laughs are even more of a priority, and the aforementioned and continually unfortunate triumph of romance over realism. To the broadening point, while most shows tend to take more comedic risks as they progress, Dream On’s relationship with its comedy has been an evolution. Beginning with a counterbalancing sense of both humor and pathos in the first few years – the kind of genre-blurring that cable finds quite artsy – and then developing a somewhat schizophrenic episodic dynamic between darker entries and lighter ones (in the middle years), Season Five appears to settle on simply being a comedic entity – the kind that, as a sitcom, might actually play well on a broadcast network. It is, to be both complimentary and derisory, becoming more “traditional.” Now, I actually don’t mind an exclusive commitment to one genre, because this removes most of the unnecessary tonal tension that contributed to the identity-related neuroses of Seasons Three and Four. Also, the turn to a more familiar modus vivendi feels organic, as the staff now consists of folks whose training and upcoming work more resembles the broadcast networks’ style. That is, they’re good at this kind of comedy.


If there’s any problem in this new comedic directive, it’s that the stories are even more idea-based, simply because these writers want bigger laughs… but have less experience with these characters. Even though the show hopes every episode is character-centric, the quest for heightened humor, also an admirable objective, sometimes overwhelms the intent – a problem usually faced by long-running sitcoms. This sense of the “usual” or “traditional” tends to define the season at large though, as Engel and his crew, just as their predecessors, further move the show into a more romantic, idealized, stylized, farcical, hyperbolic purveyor of both laughs and stories – less original; more like what we’d see, for instance, on NBC. Gone is the sense of realism that scripts in the early years would use to ground the glamorous imagery of Martin’s cinematic/televisual “thought bubbles.” Now Dream On operates with the same fictitious sense of “hyper-realism” under which most sitcoms exist. It’s not false, but it’s always elevated, offering less of a contrast to the already inflated parts of the series’ premise. None of this is worth condemning – heck, this is a more straightforward reflection of our beloved situation comedy genre – yet it does stand opposed to how Dream On was first designed. Season Five neither starts this trend or miserably follows through on it (like Season Six), but the year condones it – not always narratively; in its mere style: its comedy, its story concerns, and its general attitude. However, because Season Five removes the conflict of the prior two years and unapologetically propels the series towards its inevitable conclusion, this ends up being a smoother, easier one to enjoy, especially because the friction is gone and the laughs have increased. Furthermore, by now we’re used to improper calibration (read: premise-rejection), and with only 13 entries, it’s easy to find a handful of really funny (and generally character-focused) outings to highlight as being the best. So, I have picked five episodes that I think exemplify this season’s strongest.


Here are my picks for the five best episodes of Season Five. (They are in AIRING ORDER.)


01) Episode 85: “Steinway To Heaven” (Aired: 07/13/94)

Martin’s mother dies and leaves him with a piano and an unusual wish.

Written by Daryl Rowland & Lisa Debenedictis | Directed by Eric Laneuville


This episode’s decision to kill off one of the series’ strongest recurring assets, Martin’s mother, played by Renee Taylor (who was just beginning a recurring stint on CBS’ The Nanny), seems an unnecessarily permanent rejection of one of the most positive developments to arise out of the show’s middle era. But while the character’s death feels limiting, it does grant us one of the more dramatic episodes from the otherwise gaggy fifth season, and what’s more, because it forces Martin to deal with the grief over losing his mother (something only hinted upon in the prior year), it’s very character-driven. The reveal of Doris Tupper having dated a black man is a bit gimmicky, but the laughs are never jeopardized, nor do they encroach upon our notions of believability. Plus, we get more great guest appearances by members of Martin’s family.

02) Episode 86: “Judy And The Beast” (Aired: 07/20/94)

Judith begins dating Gibby, to Martin’s chagrin.

Written by Bill Prady | Directed by Nick Marck


I’ve consistently praised the show’s commitment to keeping character at the forefront of its objectives, and in spite of the year’s occasional flirtation with story-heavy foolishness (like in the premiere) — which is not unique to Season Five — this new staff is especially interested in doing all that it can with the characters, for they, theoretically, are more defined than the series itself (due to years of tonal drift). This is one of several entries here that most concerns itself with the dynamics between members of the ensemble — here, Martin, Gibby, and Judith (in one of her funnier episodes), as Martin becomes a green-eyed monster when his boss dates his ex-wife. Not only is this comedic and based upon the established relationships, but it also gives the rest of the series a direction; a Martin/Judith reconciliation is imminent. Memorable.

03) Episode 88: “I’m With Stupid” (Aired: 08/03/94)

Martin dates a woman who makes him feel intellectually inferior.

Written by Victor Levin | Directed by Ron Wolotzky


Of all the writers this year (including head scribe Stephen Engel, the only vet), Victor Levin does the best job (this season) of tailoring episodes around ideas designed for the comedic exploration of the characters — sans any real gimmick or functional narrative objectives (like the above’s mission statement with Martin and Judith). As with Levin’s other script for the season (highlighted below), this is one of the offerings that could be used to make a case for the shrewdness of the fifth season — in its unshackling itself from the previous tonal drama in which the series’ middle years were mired. The premise is comparably quiet (by late Dream On standards), as Martin dates a woman (Harley Jane Kozak) who is clearly more intelligent. Martin’s anxiety regarding this fact form the conflict and the comedy. Divine, simply.

04) Episode 93: “I Never Promised You Charoses, Martin” (Aired: 09/07/94)

Martin and Judith battle over Jeremy’s sudden interest in religion.

Written by Victor Levin | Directed by John Landis


My pick for the season’s best episode, this outing — another script by Levin (who would jump from this year of Dream On to the third season of Mad About You, coming up here in a few months) — is the year’s most ideal combination of character-related logically motivated plotting and big, worthwhile laughs. The story has Jeremy taking a Bible study class (Judith is a Christian), which Martin seeks to counter with information regarding Judaism (his religion). This turns into a contest between the two parents over Easter/Shabbat dinner, which naturally yields the expected avenues of comedy — especially with guests like Martin’s Aunt Sadie (Sylvia Kauders), who’s always been perfectly cast, and Judith’s parents, introduced here, played by William Schallert and Tippi Hedren. The most satisfying installment of the season — bar none.

05) Episode 94: “The Courtship Of Martin’s Father” (Aired: 09/14/94)

Martin’s father begins dating one of Martin’s closeted authors.

Written by Tom Maxwell & Don Woodard | Directed by John Landis


The last episode of the fifth season, this installment sees the return of Martin’s father (Paul Dooley), who splits with his boyfriend and comes to stay with Martin. Once again, this arc has been inherently good for the characters, forcing Martin to reconcile his feelings for his father and his father’s sexuality, and fortunately, instead of ever creeping into “Very Special Episode” territory, the episode (like its predecessors) keeps comedy paramount alongside both narrative and character integrity. The story itself has Martin unknowingly setting his father up with one of his authors, played by Kevin McCarthy, who decides to have his long-running James Bond-ish character come out of the closet (a decision with which Martin doesn’t agree). But the story is rather irrelevant; the episode is good for Martin’s character, and that’s why it’s here.


Other notable episodes that merit mention here include: “‘Tis Pity She’s A Neighbor,” which hopes to engage with the series’ established risquéness, “The Homecoming Queen,” which seems at first like a solid Martin/Eddie episode enlivened by the presence of Kim Cattrall, but soon proves itself to be too broad, convenient, and unmotivated for a full celebration, “Attack Of The 59-Inch Woman,” which returns to the possibility of a Martin/Toby romance (but at this point, doesn’t play as well as it did in years past), and “Off-Off-Broadway Bound,” which has plenty of amusing moments and boasts another theatrically-based premise.



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

“I Never Promised You Charoses, Martin”




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