Jeffrey Turns 30 - The First Film To Make AIDS Funny (And Somehow Pull It Off)

Back in 1995, I wandered into a movie theater to see a little indie LGBTQ gem called “Jeffrey”—and I walked out completely obsessed. But before we dive into the what and who of it all, I have to start with the why.

See, when the AIDS epidemic began, I was a semi-closeted teen living just outside New York City. I vividly remember the confusion, the fear, and the heartbreak as we watched so many people—especially gay men—get sick and die without understanding why. It was terrifying. That fear lingered for years, even after I came out and found myself in a long-term relationship.

So when I finally saw “Jeffrey”—a movie that dared to laugh (really laugh!) in the face of all that fear—it hit me in the heart. This was the first film to make AIDS… funny. Not disrespectful. Not dismissive. Just human. And that’s exactly why I loved it so much.

Fast-forward thirty years (yes, thirty!), and Jeffrey still stands as one of the most hilariously heartfelt and courageous comedies ever made. In honor of my recent chat with the film’s star, Steven Weber, on my Hollywood Obsessed Podcast (Episodes 139 & 140), and the movie’s big 3-0, I thought it’d be the perfect time to revisit this wild, witty, and deeply moving romantic comedy that made me laugh, cry, and, for a moment, feel completely seen.

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A Daring Comedy Born from the Heart of the Crisis

Based on Paul Rudnick’s hit stage play (he also penned the screenplay), “Jeffrey” was directed by Christopher Ashley, who originally helmed the Off-Broadway production at the WPA Theatre in 1993. Together, they assembled one of the most delightfully unexpected casts of the ’90s.

Leading the charge was Steven Weber—yes, the charming pilot from NBC’s “Wings”—who, truth be told, was my main motivation for seeing the movie in the first place. (Hey, I was a fan… and he looked great in that classic leather flight jacket.) My second reason? It was a gay-centered film—something that was finally becoming more visible and celebrated in the mid-’90s.

Weber was joined by Michael T. Weiss (soon to star in the series “The Pretender”), Bryan Batt (who later graced “Mad Men” and originated his “Jeffrey” role on stage), and in a stroke of inspired casting, “Star Trek: The Next Generation’s” very own Sir Patrick Stewart as Sterling, a fabulously witty interior decorator with impeccable taste and even sharper one-liners. Throw in cameos from Nathan Lane, Christine Baranski, Sigourney Weaver, and a whole host of scene-stealers, and you’ve got one of the most joyfully queer ensembles ever put on film.

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Love in the Time of Fear

The story unfolds in Manhattan at the height of the AIDS crisis. Jeffrey (Weber) is a gay man who’s sworn off sex—not because he doesn’t crave love, but because he’s terrified of losing it. His celibacy becomes both a shield and a prison… until he meets Steve (Weiss), a sweet, sexy, and openly HIV-positive man who challenges everything Jeffrey believes about love, fear, and connection.

Through his friends Sterling (Stewart) and Darius (Batt), and a whirlwind of hilarious cameos, Jeffrey learns that living—and loving—is always worth the risk. The result? A film that’s outrageous, touching, laugh-out-loud funny, and still, all these years later, utterly groundbreaking.

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Steven Weber Reflects

When I recently caught up with Steven Weber for the podcast, we had a deliciously candid chat about “Jeffrey”—his memories of filming it one magical summer in New York City, how he felt stepping into a gay lead role at a time when few straight actors dared, and why the movie still matters.

“It was the era where projects about LGBTQ life and AIDS were finally starting to be produced,” Weber told me. “That part of the population was finally getting a voice—beyond the stereotypical ‘gay best friend.’ “Jeffrey” was relatively groundbreaking.”

To hear the rest of our conversation (and his hilarious behind-the-scenes stories), listen HERE.

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That Dream Cast (And the Cameos We Still Can’t Get Over)

Aside from the story’s humor and heart, “Jeffrey’s” cast was a smorgasbord of fabulousness. Here are just a few highlights:

Sir Patrick Stewart (Sterling) – Watching Captain Jean-Luc Picard don a pink beret and unleash his inner diva? Pure bliss. Stewart’s flamboyant, razor-sharp Sterling is Jeffrey’s confidante and moral compass, in love with his younger partner Darius (Bryan Batt). His performance was so good, it even generated early Oscar buzz.

Steven Weber (Jeffrey) – As the neurotic yet lovable everyman, Weber gave the performance of his career. His mix of humor, vulnerability, and disbelief at his own luck made Jeffrey’s emotional journey all the more relatable.

Michael T. Weiss (Steve) – The charmingly grounded counterbalance to Jeffrey’s panic. Weiss brought quiet strength and warmth to his role as an HIV-positive man who refuses to let fear define him.

Bryan Batt (Darius) – The heart and soul of “Jeffrey.” Having originated the role on stage, Batt carried it to the screen with tenderness and humor. I also had the pleasure of chatting with Bryan on Hollywood Obsessed Podcast (Episodes 17 & 18), where he shared wonderful stories about bringing Darius to life.

Listen Now!

Episode 17 – HERE

Episode 18 – HERE

And then there were the cameos — Sigourney Weaver as a self-help guru, Nathan Lane as a hilariously conflicted priest with a love for Broadway musicals, Christine Baranski in full fabulous mode, plus scene-stealing turns from Olympia Dukakis, Kathy Najimy, Victor Garber, Debra Monk, and Peter Maloney (as Jeffrey’s parents, who try to teach him the art of phone sex — LOL), Kevin Nealon, and Gregory Jbara (as a drag queen named Angelique!). It’s the kind of cast that makes you smile just reading the credits.

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Thirty Years Later

Three decades on, Jeffrey remains as sharp, funny, and fearless as ever—a time capsule from a moment when laughter became a form of defiance. It showed audiences that humor and heartbreak can coexist, that love is always worth the risk, and that sometimes, the bravest thing you can do is simply open your heart.

So here’s to “Jeffrey”—thirty years young, still making us laugh, and still reminding us that joy is, and always will be, a radical act.

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Listen Now on Hollywood Obsessed!

Don’t miss my two-part interview with the brilliant Steven Weber—star of “Jeffrey” and “Wings”—on the latest episodes of the Hollywood Obsessed podcast!

Packed with behind-the-scenes stories, laughs, and reflections on one of the boldest comedies of the ’90s, it’s a conversation you won’t want to miss.

Listen now:

Episode 139 – HERE

Episode 140 – HERE