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Oscar the Grouch becomes an unlikely art star in Squarespace’s charming new ad

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Squarespace: A Cautionary Tale

Squarespace and Sesame Workshop have come together to create a holiday campaign where grumpy trash-dweller Oscar the Grouch is propelled into art world stardom after a fan makes him a slick website using the platform. Called A Cautionary Tale, the spot is the first holiday campaign ever created by Squarespace and coincides with Sesame Street’s 50th anniversary this year.

Speaking to It’s Nice That about the decision to partner with Sesame Workshop, Squarespace chief creative officer, David Lee, says: “We all grew up with Sesame. It’s where we learned to count, it’s where we learned to read and in some ways, it’s where we learned to dream. It brings back these nostalgic memories from the past, but feels very current and modern at the same time.”

In the 2.5-minute ad, a passer-by spots Oscar’s trash piles and mistakes them for art, making him a website to showcase his work – with Squarespace, of course. Before long, Oscar is overwhelmed with fans, invited to exhibit at some of the city’s biggest museums and to star on chat shows. Finally, a museum dedicated to his work is opened – needless to say the fuzzy green misanthrope is less than thrilled.

“We like Oscar because he’s a bit curmudgeon and a naysayer in the most charming, lovable way,” says Lee. “We could define him as a modern-day Scrooge, but Oscar is ultimately someone who is misunderstood. Through this story, we’re encouraging everyone to take whatever dreams they may have and turn them into a reality.”

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Squarespace: A Cautionary Tale

Inspired by the saying “One person’s trash is another person’s treasure,” the Squarespace creative team thought Oscar would be an ideal character to illustrate the idea of an accidental artist discovered on the streets of New York. “His misery is ultimately what makes him happy, and we wanted to find a funny yet charming way to bring this story to life during the holiday season that both kids and adults would find inspiring yet entertaining,” says Lee.

The ad has a loving jab a the city’s art scene, mocking the pretentiousness of curators and the superficiality of buyers that will literally buy trash on the back of hype. The campaign is also an ode to the Big Apple, where both Sesame and Squarespace have roots. “Oscar really exemplifies the cynical, misunderstood New Yorker,” says Lee. “We wanted to find a way to capture the spirit, the hustle and the energy of this city as part of the journey to fame in this modern day tale. Ultimately, there is this unwritten notion that if you can make it here, you can make it anywhere.” Unfortunately for Oscar, “making it” is not an ambition he ever even had.

For Lee and the creative team, putting Oscar in unusual contexts was one of the most fun parts of the project. “What’s the least grouchy place Oscar could be? In the back of a stretch Cadillac, of course,” says Lee. In the edit, the team were able to push the joke even further by double exposing the limo scene with an endless stream of magazine covers – an homage to Orson Welles’ Citizen Kane. “Oscar is such a rewarding character to write because the best things that can happen to him are the worst things that can happen to him,” adds Lee.

Alongside the spot, Squarespace has also created 25 limited edition art capsules in collaboration with NYC garbage artist Justin Gignac, which will be sold to raise money for Sesame Workshop’s charitable work with children. They can be bought here.