Honestly, if you grew up watching NBC’s Must See TV, you probably have a core memory of Jack McFarland clutching a plastic doll and hyperventilating in a restaurant. It was 2000. Peak sitcom era. And the will and grace cher episode—officially titled "Gypsies, Tramps and Weed"—didn't just give us a celebrity cameo. It gave us one of the most meta, self-aware moments in television history.
The Slap Heard Round the World
Most guest stars on Will & Grace played a character. Not Cher. She played herself, or at least, a version of herself that was cool enough to wander into a random New York eatery and get into a fight with a fan.
The setup is basically legendary: Jack is obsessed with his new Cher doll. He’s treating it like a living person, giving it a booster seat at the table, the whole nine yards. When the actual, real-life Cher walks by, Jack doesn't recognize her. Why? Because in his head, no real person could ever look that much like Cher.
He literally tells her, "You’re a little too big to be doing Cher, but the look? Not bad."
He thinks she’s a drag queen. He even critiques her "act." The irony of Jack McFarland, a man who built his entire personality around Cher worship, failing to identify the Goddess of Pop to her face is comedy gold. It leads to the moment everyone remembers: Cher trying to prove her identity, Jack remaining skeptical, and Cher finally losing it.
👉 See also: New Movies in Theatre: What Most People Get Wrong About This Month's Picks
"Snap out of it!" she yells, delivering that iconic Moonstruck slap.
Why the Cher Doll was a Secret Genius Move
Kinda weird, but that doll wasn't just a random prop. It was a massive marketing collaboration between NBC, Mattel, and the show’s writers. They actually timed the episode to coincide with the real-world launch of the Cher Barbie.
The "prototype" Jack carries around became a cult object overnight. After the episode aired, over 1,200 people flooded Mattel's website just to get on a mailing list for it. Today, those original dolls are collectors' items. Some reports claim the specific prototypes used on set are worth tens of thousands of dollars now.
Behind the Scenes of the Cameo
Cher didn't spend weeks on set. Megan Mullally later mentioned in interviews that Cher was basically "airlifted" in. She arrived in full "Cher Land" gear, filmed her scenes on October 17, 2000, and was gone.
✨ Don't miss: A Simple Favor Blake Lively: Why Emily Nelson Is Still the Ultimate Screen Mystery
Interestingly, there were two endings filmed. Cher actually improvised one of them where she did something completely different to Sean Hayes that allegedly made him almost pass out from shock. The version we got—the slap—was the one the producers felt fit the rhythm of the show best, but the energy of that improvisation stayed in the final cut. You can see it in Sean Hayes' eyes; he isn't just acting. He is a genuine superfan losing his mind.
The Return in Season 4
A lot of people forget this wasn't her only appearance. She came back for the Season 4 finale, "A.I.: Artificial Insemination."
This time, it wasn't a "real world" meeting. Jack is having a crisis about his career and decides to give up acting to become a "retail queen" at Barney’s. Cher appears to him in a dream sequence as a literal goddess on a throne. It's less grounded than the first appearance, but it solidified the idea that in the Will & Grace universe, Cher isn't just a singer. She’s Jack’s spiritual guide.
The Cultural Impact
Back in 2000, having an A-list icon like Cher on a show with two gay leads was a massive statement. It wasn't just about ratings—though the ratings were huge. It was about validation.
🔗 Read more: The A Wrinkle in Time Cast: Why This Massive Star Power Didn't Save the Movie
- Mainstream Acceptance: It signaled that the show had moved past being a "gay Seinfeld" niche hit and into a cultural phenomenon.
- The "Diva" Archetype: It leaned into the specific relationship between gay men and their idols without making the joke mean-spirited.
- The Slap: It turned a movie quote into a permanent TV trope.
The show eventually leaned a bit too hard on the "guest star of the week" gimmick (remember the Madonna episode?), but the Cher spot felt organic. It worked because Jack’s obsession had been a running gag since the pilot.
What to do if you're Re-watching
If you’re diving back into the series on streaming, don't just skip to the cameo. The "Gypsies, Tramps and Weed" episode actually has a really funny B-plot where Grace hires a guy who ends up selling pot out of her design firm.
It’s a snapshot of a very specific time in New York history. The fashion is... questionable. The jokes are fast. But the chemistry between the core four—Will, Grace, Jack, and Karen—is why the show worked. Cher was just the glitter on top of the sundae.
Next Steps for Fans:
- Check out the Season 3 DVD outtakes if you can find them; the alternate takes of the restaurant scene show just how much fun Cher was having.
- Look up the Mattel "Timeless Treasures" Cher doll to see the actual version of the prop Jack was obsessed with.
- If you're a completionist, watch the Season 4 finale "A.I.: Artificial Insemination" immediately after to see the evolution of Jack’s "relationship" with his idol.