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

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 – a 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.