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

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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