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5 Reasons Whoopi Goldberg’s Cheshire Cat Is The Weirdest, Most Iconic Adaptation You Forgot About

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Step into a cinematic rabbit hole that time almost forgot. While the Disney classic and Tim Burton's blockbuster often dominate the conversation, a truly unique and polarizing version of Lewis Carroll's tale emerged in 1999, featuring an all-star cast and some incredibly ambitious, if unsettling, special effects. This made-for-TV movie, produced by Hallmark Entertainment, is primarily remembered today for one bizarre, unforgettable character: the Cheshire Cat, voiced and visually represented by the incomparable Whoopi Goldberg. This December 2025, we revisit this cult classic to understand why this particular incarnation of the grinning feline continues to spark fascination and debate among fans of Wonderland lore.

The 1999 adaptation of Alice in Wonderland dared to be different, blending live-action with early, experimental CGI and puppetry. Whoopi Goldberg’s involvement was a major coup, lending her distinct, gravelly voice and unmistakable persona to the philosophical, disappearing cat. Her portrayal is a masterclass in voice acting, yet the visual execution—mapping her face onto a CGI cat—is what cemented the character’s place in the pantheon of strange cinematic choices, making it a must-watch for anyone curious about the limits of late-90s television fantasy.

Whoopi Goldberg: A Profile in EGOT Excellence

Whoopi Goldberg, born Caryn Elaine Johnson on November 13, 1955, in Manhattan, New York, is one of the most accomplished and recognizable entertainers in the world. Her career spans comedy, acting, singing, and television hosting, cementing her status as a cultural icon and a trailblazer in Hollywood.

  • Full Name: Caryn Elaine Johnson
  • Born: November 13, 1955 (Age: 70 in 2025)
  • Birthplace: Manhattan, New York, U.S.
  • Occupation: Actress, Comedian, Author, Television Personality, Producer
  • Major Career Milestones:
    • EGOT Winner: One of the few artists to have won an Emmy, Grammy, Oscar, and Tony Award.
    • Oscar Wins: Best Supporting Actress for *Ghost* (1990). Nominated for Best Actress for *The Color Purple* (1985).
    • Filmography Highlights: *The Color Purple*, *Ghost*, *Sister Act* (1 & 2), *The Lion King* (voice of Shenzi).
    • Television Career: Longtime moderator and co-host of the daytime talk show *The View* since 2007.
    • Other Notable Roles: Appeared as a center square in the reboot of *Hollywood Squares*.
  • Role in *Alice in Wonderland* (1999): Voice and facial model for the Cheshire Cat.

The 1999 Adaptation: A Star-Studded, CGI Fever Dream

The 1999 *Alice in Wonderland* TV movie, directed by Nick Willing, was an ambitious project by Hallmark Entertainment. It aimed to be a visually spectacular and faithful rendition of Lewis Carroll’s classic novels, *Alice's Adventures in Wonderland* and *Through the Looking-Glass*.

The film boasted an incredible ensemble cast of British and American stars, turning the production into a major television event. This sheer volume of celebrity talent is one of the film's most enduring legacies, creating a Who's Who of late 90s cinema and television.

Key members of the star-studded cast included:

  • Tina Majorino as Alice
  • Martin Short as The Mad Hatter
  • Miranda Richardson as The Queen of Hearts
  • Robbie Coltrane as Tweedle-Dum
  • George Wendt as Tweedle-Dee
  • Ben Kingsley as Major Caterpillar
  • Gene Wilder as The Mock Turtle
  • Peter Ustinov as The Walrus

Despite the star power, the film received generally mixed-to-negative critical reception upon release, though some audiences appreciated its visuals and faithfulness to the source material. The special effects, while groundbreaking for a television movie at the time, are what often draw the most scrutiny in retrospect.

5 Iconic Elements of Whoopi Goldberg's Cheshire Cat

Whoopi Goldberg's portrayal is far more than just a voice role; it’s a fully integrated, though technologically challenging, performance. The character serves as Alice’s cryptic guide and philosophical foil, teaching her "the rules" of Wonderland.

1. The Polarizing Face-Mapping CGI

The most discussed and controversial aspect of the 1999 Cheshire Cat is the visual effect itself. Instead of a traditional animated or puppet cat, the filmmakers used early CGI to map Whoopi Goldberg's actual face onto the body of the grinning cat. This technique, intended to give the character a distinct and expressive human quality, often resulted in an effect that viewers found uncanny and slightly unsettling—a "horror" for some, a "fever dream" for others.

This visual choice instantly sets the 1999 version apart from all others, including the classic Disney cartoon and the later Tim Burton films. It’s a perfect example of a late-90s special effect that was ahead of its time but limited by the technology available, creating a truly unique and slightly bizarre aesthetic.

2. The Perfect Voice for Cryptic Wisdom

Goldberg's distinctive, deep, and comedic voice is ideally suited for the Cheshire Cat’s role as the wise, yet maddeningly vague, mentor. Her vocal performance brings a necessary gravitas and a playful, cynical edge to the character’s lines. She delivers the Cat’s famous paradoxes and philosophical musings with a dry wit that perfectly captures the essence of Lewis Carroll's logic-bending dialogue. Her voice ensures the Cat is both comforting and deeply mysterious.

3. A Cat Who Teaches "The Rules" of Wonderland

In this particular adaptation, the Cheshire Cat’s role is clearly defined as the one who initiates Alice (Tina Majorino) into the bizarre logic of Wonderland. The Cat is explicitly tasked with explaining "the rules" of the illogical land, acting as a crucial bridge between Alice’s reality and the fantasy world.

This narrative function makes the Cheshire Cat more central to the plot than in many other versions, using Goldberg's authoritative yet mischievous delivery to ground the story’s surrealism.

4. A Masterclass in Star-Powered Voice Acting

Goldberg’s casting is a prime example of the 1999 film’s strategy of using massive star power to elevate a TV movie. While the film is not a traditional animated feature, her performance is part of a long tradition of major actors lending their voices to iconic animated and CGI characters, a practice that has only grown more common in the decades since. Her presence alone made the film a notable entry in the crowded field of *Alice* adaptations.

5. An Enduring Source of Cult Nostalgia

Decades after its premiere, the 1999 *Alice in Wonderland* has achieved a kind of cult status, largely driven by the sheer oddity of its casting and special effects. The image of Whoopi Goldberg’s face floating in the darkness as the Cheshire Cat is a powerful piece of visual nostalgia for a generation that watched it on NBC or Hallmark Channel reruns. It’s a film that, for all its technical flaws, is genuinely unforgettable and serves as a fascinating time capsule of late 20th-century television fantasy production. The continuous online discussion, even years later, proves its lasting, if weird, impact.

Why the Whoopi Goldberg Cheshire Cat Remains Relevant

The enduring fascination with Whoopi Goldberg's Cheshire Cat speaks to the power of unique character design and bold casting choices. While the CGI may appear dated by modern standards, the decision to use a face-mapped celebrity cemented the character's legacy as a truly distinct vision of Lewis Carroll's creation.

In a world saturated with *Alice in Wonderland* adaptations, the 1999 version, with its star-studded cast and its famously uncanny feline, carved out a permanent niche. It reminds us that sometimes, the most memorable characters are the ones that take the biggest, strangest risks, leaving audiences with a visual memory that is impossible to shake—a truly grinning, disappearing face that is half cat, half EGOT legend.

The film, and specifically Goldberg’s Cat, continue to be discussed on forums and social media, often introduced to new generations as a piece of bizarre cinematic history. This continuous interest ensures that the 1999 *Alice in Wonderland* will remain a crucial, if sometimes bewildering, chapter in the long history of Wonderland on screen.

5 Reasons Whoopi Goldberg’s Cheshire Cat is the Weirdest, Most Iconic Adaptation You Forgot About
cheshire cat whoopi goldberg
cheshire cat whoopi goldberg

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