You probably remember the grin. Not just any grin, but a wide, toothy, distinctly "Whoopi" beam that floated mid-air against a backdrop of late-nineties CGI. If you grew up in the late 90s or early 2000s, Whoopi Goldberg as the Cheshire Cat in the 1999 television movie Alice in Wonderland wasn't just a performance. It was a core memory.
It’s weird how certain versions of Lewis Carroll’s fever dream stick with us. Some people swear by the 1951 Disney animation. Others like the gothic, slightly over-the-top Johnny Depp era. But for a very specific generation, the definitive version of the pink-and-purple feline is Whoopi.
Honestly, the casting was a stroke of genius. Whoopi Goldberg brought this specific brand of "cool aunt" energy to a character that is usually played as either genuinely insane or deeply sinister. Her Cheshire Cat was different. She was a vibe. She was relaxed. She was arguably the only person in Wonderland who wasn't totally stressed out.
The 1999 NBC Odyssey
This wasn't some low-budget theater production. When NBC aired Alice in Wonderland in February 1999, it was a massive "Event Series" back when network television still had the budget to do that. They threw everything at the wall. We’re talking about a cast that included Ben Kingsley as the Major Caterpillar, Martin Short as the Mad Hatter, Christopher Lloyd as the White Knight, and Gene Wilder as the Mock Turtle.
Tina Majorino played Alice. She had those big, expressive eyes and a sense of genuine confusion that made the whole thing work. But even among all those heavy hitters, people mostly talk about the cat.
The production used Jim Henson’s Creature Shop for the visual effects, which is why the movie has that tactile, slightly eerie feel. It’s a mix of early digital compositing and old-school puppetry logic. Whoopi’s face was essentially mapped onto the feline body, creating a "uncanny valley" effect that was groundbreaking at the time. Today, it looks a bit dated, but in 1999? It was high art.
👉 See also: The Entire History of You: What Most People Get Wrong About the Grain
Why Whoopi Goldberg as the Cheshire Cat Actually Worked
Most actors play the Cheshire Cat with a high-pitched, manic giggle. Think Sterling Holloway in the Disney version. But Whoopi went the other way. She kept her signature raspy, low-register voice. It made the cat feel like a weary observer rather than a participant in the madness.
"I'm not crazy," the character seems to say through Whoopi's delivery. "I just live here."
There is a specific scene where Alice is frustrated, trying to figure out which way to go. Whoopi's cat doesn't mock her. She just lays out the existential reality of the place with a shrug. It’s the ultimate "it is what it is" performance. This nonchalance is exactly why the clips still go viral on social media. In a world that feels increasingly like Wonderland—random rules, loud voices, nonsensical logic—Whoopi’s Cheshire Cat is the patron saint of staying unbothered.
The Design Choice
They didn't try to hide Whoopi. Often, when big stars do voice work or "creature" roles, they disappear. Not here. The designers kept her iconic look. You could see the dreadlocks. You could see the specific way she arched her eyebrows.
The color palette was bold. Neon purples and electric blues. It was a departure from the more muted, Victorian illustrations by John Tenniel. This was Wonderland for the Y2K era—bright, digital, and a little bit loud.
✨ Don't miss: Shamea Morton and the Real Housewives of Atlanta: What Really Happened to Her Peach
A Masterclass in Cameo Acting
Whoopi wasn't on screen for long. That's the nature of the Cheshire Cat; you show up, say something cryptic, and vanish. But her screentime is the anchor of the second act.
Interestingly, this version of Alice followed the book's structure more closely than most, but it added a framing device. Alice is nervous about performing a song at a garden party. The whole journey through Wonderland is essentially a dream-fueled pep talk. Whoopi’s role in that pep talk is crucial. She represents the realization that you can't please everyone because "everyone here is mad."
If you haven't rewatched it lately, the dialogue holds up surprisingly well. It’s snappy. It doesn't talk down to kids. Whoopi delivers lines about the Queen of Hearts' temper with the same casualness someone might use to describe the weather. It’s that contrast—the horrific threat of decapitation met with a calm feline grin—that creates the tension Carroll intended.
The Legacy of the 1999 Cast
It’s worth noting that this film came out right as Whoopi was cementing her status as a multi-hyphenate mogul. She was already an EGOT (Emmy, Grammy, Oscar, Tony) winner. She could have phoned it in. She didn't.
- Gene Wilder as the Mock Turtle: He sang "Beautiful Soup" with a melancholy that actually made you feel bad for a fictional turtle.
- Martin Short as the Mad Hatter: Pure, unadulterated physical comedy.
- Miranda Richardson as the Queen of Hearts: Her "Off with their heads!" is arguably the most shrill and terrifying version ever put to film.
Why We Are Still Talking About It in 2026
Nostalgia is a powerful drug, but it’s not just that. We’re currently seeing a massive resurgence in 90s aesthetic. The "Kidcore" movement on platforms like Pinterest and TikTok thrives on the exact visual language used in this movie. The saturated colors, the clunky but charming CGI, and the star-studded ensemble.
🔗 Read more: Who is Really in the Enola Holmes 2 Cast? A Look at the Faces Behind the Mystery
Moreover, Whoopi Goldberg remains a constant in the cultural conversation. Whether it's The View or her various acting returns, she's never left the public eye. When people discover she played this role, it’s a "wait, really?" moment that leads to a rabbit hole of clips.
The 1999 Alice in Wonderland hasn't been scrubbed from existence, but it’s not always the easiest to find on major streaming platforms compared to the Disney versions. This "rarity" gives it a cult status. It feels like a secret shared by people who stayed up late to watch the original broadcast.
How to Revisit the Magic
If you want to track down this specific performance, you have a few options. It’s often tucked away on niche streaming services or available for digital purchase on Amazon and Vudu.
Don't expect 4K Marvel-level graphics. You have to appreciate it for what it is: a peak-90s television experiment. The CGI "glow" around the characters is part of the charm. It looks like a moving storybook from a decade that was obsessed with the future but still had its feet in theatrical traditions.
Real Talk: Is it Scary?
Some parents wonder if this version is too intense. Honestly, it’s a bit trippy. The Red King’s dream sequence and the trial at the end have some surrealist elements that might freak out a very young toddler. But for school-aged kids? It’s perfect. It’s weird in the way childhood is weird. Whoopi’s presence actually acts as a safety blanket. Every time she appears, the tension breaks. You know Alice is going to be okay because the cat is too cool to let things truly go sideways.
Actionable Steps for Fans and Collectors
If you're looking to dive back into the world of Whoopi’s Wonderland, here is how to do it right:
- Check Local Libraries: Many libraries still stock the Hallmark Entertainment DVD sets. It’s often packaged with other 90s fantasy films like The 10th Kingdom or Gulliver's Travels.
- Look for the Soundtrack: The music by Richard Hartley is actually quite sophisticated. The Mock Turtle’s song is a standout if you appreciate Gene Wilder’s specific brand of musical whimsy.
- Compare and Contrast: Watch Whoopi’s scenes alongside Stephen Fry’s version (from the Tim Burton films). It’s a fascinating study in how British vs. American sensibilities interpret the same character. Fry is more intellectual/sarcastic; Whoopi is more "street-smart" and philosophical.
- Digital Archives: If you can't find a physical copy, check YouTube. Because of its age and "TV movie" status, many of the best scenes have been uploaded by fans and haven't been struck down by copyright bots in years.
Whoopi Goldberg as the Cheshire Cat remains a masterclass in how to make a brief role iconic. She didn't need two hours of screentime. She just needed a grin, a shrug, and that unmistakable voice to leave a permanent mark on the history of Wonderland.