Trivia - Dream On

Back in 1990, HBO took its first big swing at original programming and gave us one of its earliest TV series: “Dream On”—an adult sitcom about a divorced New York City book editor juggling his family life, career, and ahem very active love life. And let’s be honest, for an average-looking white guy, Martin Tupper sure managed to bed a lot of very sexy women. (He was the Picasso of bedroom disasters.)

What made the show such a hit? For starters, no one had ever seen a sitcom like this before. It had adult language, surreal cutaway gags using vintage film clips, and plenty of nudity—mostly women with very large... hearts. By today’s standards it’s practically PG-13, but back then, viewers were clutching their pearls and saying, “They can show that on TV?!”

But beyond the buzz, "Dream On" was genuinely hilarious—created by David Crane and Marta Kauffman (yes, the Friends masterminds) and packed with a killer cast: Brian Benben, Chris Demetral, Denny Dillon, Wendie Malick, Dorien Wilson, and Michael McKean. Oh, and let’s not forget the epic guest stars—from David Bowie to Sylvester Stallone!

In honor of my latest interview with one of the stars of this laugh-a-minute ’90s gem—Christopher Demetral—featured in Episodes 127 & 128 of Hollywood Obsessed, I thought it’d be fun to take a nostalgic trip back... and test your "Dream On" trivia skills.

So are YOU ready? Let’s “Dream On!”

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John Landis (“An American Werewolf In London”) asked Universal Studios if he could make a show out of all the old television programs that Universal had in its library, a lot of which were anthology shows. He then asked writers David Crane and Marta Kauffman to come up with a premise. “Dream On” was the result.

“Dream On” was executive produced by Kevin Bright and John Landis. Landis also directed several episodes of the series.

The show was notable for its frequent use of clips from old movies and TV shows to express Martin's inner life and feelings, which lent it much of its quirky appeal, reminding viewers about the impact of TV on their consciousness. The show was also significant for being one of the first American sitcoms to use uncensored profanity and nudity.

“Dream On” first aired July 1990 on HBO, and was cancelled by HBO in March 1996.

The opening credits began with a television set turning on to display nothing but static. This has since become the generic logo for all HBO Original Series.

"Dream On" was one of the first original series produced by HBO. 

Nudity was a signature part of “Dream On” from the very beginning—typically featuring at least one R-rated scene per episode. Why? Because executive producer John Landis, who had full creative control, insisted on it. And true to form, HBO never objected.

Actor Brian Benben admitted in an interview with Entertainment Weekly that he “didn’t use a stunt butt” when his character had a nude scene in the season three premiere.

Wendie Malick (Judith Tupper Stone) would go onto co-star with David Hyde Pierce (Jerry Dorfer) on the very last season of “Frasier.”

Michael McKean, who played a regular on the show, was also a regular on "Saturday Night Live." While he appeared in five episodes of "Dream On" of season two, the show left the door open for him to return for more episodes if his schedule allowed. 

In 1993, child actor Chris Demetral won a Young Artist Award in the category Best Young Actor Starring in a Cable Series for his work as Jeremy Tupper on “Dream On.”

The character of Eddie Charles, was originally played by Jeff Joseph and was replaced by a different actor partway through the first series by Dorien Wilson. This is explained away by having him get surgery to change his eyelids. So he gets a whole new face and several extra inches of height! However, everybody says that he doesn't look any different. Martin quips "A little younger maybe." Devillishly clever, these eyelid surgeons!

Barbara Alyn Woods appeared on "Dream On" in two different roles: first as “Linda” in Season 3, Episode 21 (“It Came from Beneath the Sink”), and later as “Phoebe” in Season 6, Episode 5 (“9½ Days”).

Courtney Cox appeared on the season 3 episode “Come and Knock on Our Door…” where Martin and Eddie meet Alisha (Cox) at an awards banquet and end up in her hotel room and have a threesome. Cox later became one of the main stars on the TV series “Friends,”  which was also created by David Crane and Marta Kauffman.

When Brian Benben was asked to audition for the HBO comedy series "Dream On", he was one of the few people immediately to understand its concept.

Denny Dillon received a CableACE Award in 1995 "Best Actress in a Comedy Series" for her role as Toby Pedalbee in HBO's “Dream On”

Brian Benben appeared in two films—“Radioland Murders” and “I Come in Peace”—that failed at the box office, and he was primarily known for his role as Martin Tupper until finding later success with “Imposters” and “Private Practice.”

The series had many notable guest stars including Eva Gabor, Sylvester Stallone, Mimi Rogers, Stephen Furst, Tom Berenger, David Bowie, Fran Drescher, Kathy Kinney, Larry Miller, Dan Castellaneta, Ray Walston, Pat Paulson, George Hamilton, and Teri Garr.

In Season 3, Episode 19 (“The Son Also Rises”), the "girl" that 13-year-old Jeremy (played by Chris Demetral) makes out with was actually 19-years-old when the episode was filmed. The age difference between the actors was approximately 3½ years.

Legendary movie star Tippi Hedren (“The Birds”) played Judith’s (Wendie Malick) mother on the series. She said, the sitcom gave her "the opportunity to do comedy. I'd never done comedy before and it was just wonderful for me to be able to do that.”

In 2014, GQ magazine listed the pre-“JAG” Catherine Bell exposing her breasts (season 5, episode 9) as the 4th most underrated nude moment in TV history.

Actor Chris Demetral, who played Jeremy Tupper, attended Macomb Community College in Clinton Township, Michigan, from 1994 to 1995. He did this to escape the Hollywood limelight for a little while, even though he was commuting back and forth between California and Michigan to film his scenes for HBO's “Dream On”.

Martin’s neurotic ex-wife Judith (played by the hilarious Wendie Malick) was constantly gushing about her new husband—Mr. Perfect—a doctor with two Nobel Prizes, a Grammy, and even a "Sexiest Man Alive" title from People magazine. But here’s the kicker: we never see him... until the very last episode of the series!

In the TV series “Dream On”, Judith's husband, Richard Stone, was played by Paul Michael Glaser in the episode "The Second Greatest Story Ever Told". 

"Dream On" often aired alongside "The Larry Sanders Show," another HBO sitcom known for its satirical take on late-night talk shows. 

Jason Alexander, best known for his role as George Costanza on “Seinfeld,” appeared in an episode of the HBO sitcom “Dream On.” He guest-starred as Randall Townsend, a sleazy lawyer who goes head-to-head with James Woods' character in a legal case. For his performance, Alexander was nominated for a Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series in 1994.

Paul Dooley had an Emmy-nominated guest turn on the HBO sitcom “Dream On,” playing the gay father of the lead character, Martin Tupper (played by Brian Benben).

When "Dream On" was rebroadcast on the Fox network, episodes were re-edited to remove swearing, tone down the sex, and remove nudity.

While the show ran for six seasons and produced 120 episodes from 1990 to 1996, HBO did not own the show outright, as it was produced by MCA Television Entertainment, which later became part of NBC/Universal.

The cancellation of “Dream On” is primarily attributed to music and film rights issues, which made it difficult to stream or make available online.

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Trivia facts lovingly sourced from IMDb and Wikipedia—because even the most devoted fans need a little fact-check now and then!

And don’t forget to check out my exclusive two-part interview with Jeremy Tupper himself—Christopher Demetral—on the latest episodes of the Hollywood Obsessed podcast! It’s a must-listen conversation that dives into the highs, the hardships, and the human side of growing up in the spotlight.

Episode 127 - HERE

Episode 128 - HERE