A Look Back at the Annie Leibovitz-Disney Collab That Still Has Us Asking Questions

In 2007, the legendary photographer began shooting celebs as Disney characters and the results were never not…interesting
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For most people, the words “Disney live-action remake” might evoke the haunting image of a blue Will Smith and his freaky little Genie ponytail.

But in 2007, back when the Walt Disney Corporation was just a conglomerate and not yet a behemoth that shits out one Star Wars movie a year, things were moving in a more inspired direction. Disney hired Annie Leibovitz to photograph a bunch of A-list celebrities as classic Disney characters in a series of promotional photos for the Disney Parks. Yes, Annie Leibovitz—the acclaimed celebrity portrait photographer, the same woman who captured John Lennon and Yoko Ono in bed for Rolling Stone; the first woman ever with a solo exhibition at the National Portrait Gallery; the woman whose work has appeared in Vogue, Vanity Fair, and countless other publications—got paid extremely fat stacks by “the big D” to create some of the most legendary cosplay photos of all time.

Leibovitz’s Disney Dream Portraits are a tantalizing glimpse at what might have been: a multicultural, dazzling, sometimes baffling, always entertaining vision of the animated Disney classics as live-action masterpieces. Only someone as uncompromising in their vision as Annie Leibovitz could have dared to dream of a world where Gisele Bundchen and Mikhail Baryshnikov are Wendy and Peter Pan.

This is fully unhinged in all the best ways. Casting an aged ballet dancer as “the boy who never grew up?” I have no choice but to stan. Nothing says “British schoolgirl Wendy Darling” like world-famous Brazilian supermodel Gisele Bundchen. Note the tiny cameo from Tina Fey as Tinkerbell, because, why the fuck not?!

Some of the casting choices are absolutely inspired, like Scarlett Johansson as Cinderella. This singular image blows Kenneth Branaugh’s joyless 2015 remake of Cinderella right out of the water. And yes, those trees in the background are played by ScarJo as well. Multitalented queen.

Under the grinding weight of Disney’s reboot machine, Leibovitz’s offbeat casting choices feel refreshing. Feast your eyes on the bizarre yet enticing pairing of Jeff Bridges and Penelope Cruz as Beast and Belle.

Penelope Cruz as Belle, the French inventor’s daughter? Why not! Jeff Bridges as a ghastly, beastlike creature? Absolutely! This photo is edgy, unexpected, and 900 percent more entertaining than the CGI, autotuned nightmare that was 2017’s live action Beauty and the Beast. I’ll never forget watching Emma Watson go full T-Pain on “Bonjour.”

The hits just keep on coming, as evidenced by J.Lo and Marc Anthony as Jasmine and Aladdin. As someone who’s still confused by Guy Ritchie’s Bollywood sequences in Aladdin (India ≠ Arabia), I find this image of a then-coupled J.Lo and Marc Anthony so very soothing. It has it all: drama, mystery, and romance—and that’s just me talking about Marc Anthony’s puffy shirt.

Annie didn’t stop there—she proceeded to officially “go off” with the inspired casting of Whoopi Goldberg as the Genie. For those of us who enjoy Whoopi’s line of ganjapreneurial THC-infused products, casting her as a magical genie is quite apt. It’s no secret that Whoopi is magic personified. I mean, the woman regularly bodies Meghan McCain on The View, so she’s granting my wishes every damn day.

Some of Leibovitz’s casting choices are predictable, like Taylor Swift as Rapunzel. This one is too perfect. A golden-haired goddess “trapped” in a tower who’s constantly moaning and bitching that she’s trapped by an “evil witch.” Sound familiar? Substitute Kim Kardashian or Scooter Braun for the evil witch or Spotify for the tower she’s “trapped in”—honey, we all know that tower has stairs. You’re not fooling anyone.

Other choices Leibovitz made verge on the sublime, such as Julianne Moore as Ariel. No shade to my queen Halle Bailey, but Julianne Moore is my ~one true Ariel.~ Casting a then-48-year-old legend to play a 16-year-old sex fish? ANNIE. DID. THAT. Huge shout out to Michael Phelps, who’s featured as a nameless merman in this shot. What should be a huge moment for merfolk visibility turns out to be a tragic moment for Phelps, whose blurry back is the only actual part of him featured. That’s right, Leibovitz cast a 23-time Olympic Gold medalist only to showcase his faceless, muscular physique. Savage.

But one portrait veers into the absolutely bizarre: Beyoncé as Alice in Wonderland. What in the WHAT? How on earth did Annie settle on casting Queen Bey in the role of Alice, a naive, wide-eyed, little girl, the poster child for irresponsible hallucinogen use? Only someone as creatively daring as Annie Leibovitz would dare to miscast Beyoncé in this way. Things only become more confusing when you realize Leibovitz filled out the teacup with Lyle Lovett and Oliver Platt, of all people. Seriously, just try to name a more confusing trio! Just looking at this photo makes me feel like I’m having a bad trip. For Beyoncé’s portrait as Alice, Annie went the extra mile and had 700-lb teacups shipped from Disneyland to her farm in Upstate N.Y. I can only dream of making Disney pay a UPS bill that high.

If I’m being straight up, the aggressive addition of yas qween #girlboss politics into the recent live-action remakes feels cloying and forced. Like, was I really supposed to think Emma Watson’s Belle is a badass feminist because she randomly INVENTED WASHING MACHINES in the Beauty and the Beast remake? So unnecessary! In light of Disney’s attempts at feminist virtue-signalling, Leibovitz’s portraits seem wildly unwoke, like this photo of Jessica Biel as Pocahontas that would make Elizabeth Warren cringe. Or Zac Efron seemingly groping a roofied Vanessa Hudgens as Sleeping Beauty.

My vagina still has a soft spot for aughts-era Russell Brand. Those beachy waves, that guyliner, his barely buttoned shirt sloppily tucked into 14 studded belts. Russell Brand was THAT BITCH. The only thing wetter than Captain Hook’s pirate ship were my damn jorts after looking at this photo for the first time.

Annie Leibovitz early years hauser and wirth
Annie Leibovitz on a photo shoot with Jessica Chastain

Photo by Scott Brinegar/Disney Parks/Getty Images

The Disney Dream Portraits proved so successful that the series continued until 2014, ultimately yielding 23 magnificent, absolutely under-appreciated photos. I, for one, am absolutely disgusted with the blatant erasure of Leibovitz’s portraits in the current era of Disney live-action remakes. The makers of those films should be name checking and giving proper credit to Annie at every opportunity.

I’d go so far as to say, to true Disney fans, Leibovitz’s Disney Dream portraits are canon and the live-action Disney remakes are not. I’m sorry but the Lady and the Tramp reboot that looked more like a 1-800-Pet-Meds commercial than a movie? Miss me with that, Bob Iger. If it were up to Annie, we’d have Shia LaBeouf and Lady Gaga in full dog suits eating spaghetti. And that’s the kind of magic I want.

Follow Caroline on Instagram at @officialseanpenn.


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