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Squarespace Advertising Sesame Street

Oscar the Grouch becomes a reluctant art star in Squarespace’s holiday ad


By Kyle O'Brien, Creative Works Editor

November 25, 2019 | 3 min read

Sesame Street’s Oscar the Grouch revels in being alone and miserable. So imagine the trash-loving Muppet’s surprise when he becomes a celebrity artist thanks to a website by Squarespace.

Oscar the Grouch

Oscar the Grouch for Squarespace

In a short film titled ‘A Cautionary Tale’ - a woman discovers Oscar’s talent for piling his trash findings into artistic sculptures. Fervent in the belief that the world needs to know about his art, she builds him a Squarespace website. And, as he protests, his trash can is swarmed by people coming to take a look.

The Squarespace website promptly becomes an instant hit and soon the Grouch becomes famous, with his own installation and eventually his own ‘Contemporary Trash Museum.’ Through it all, he keeps telling people to “scram” and says his newfound fame as Oscar the Artist is the worst thing ever to happen to him.

In a revelation at the end of the film, he tells a crowd of reporters outside the museum that, even though he’s a famous artist, he’s never been more miserable in his life - a fact that quickly turns into a positive when he realizes that his misery is due to the Squarespace website.

The collaboration between Squarespace and Sesame Workshop comes on the occasion of Sesame Street’s 50th Anniversary. As part of the campaign, limited edition art capsules inspired by Oscar's unlikely rise in the art world were created in collaboration with Squarespace customer and New York City garbage artist Justin Gignac. Only 25 capsules were made and all are numbered and signed by Oscar the Grouch. All proceeds will be directly routed to Sesame Workshop to support its mission to help children everywhere grow smarter, stronger and kinder.

The capsules will be available starting 25 November and sold on

“As a fellow New York-based company, Squarespace is proud to partner with Sesame Workshop to demonstrate how art is a timeless form of self-expression, and inspire people of all ages to follow their dreams. We share in Sesame Workshop’s commitment to supporting creativity, imagination and self-expression for all generations, and we hope our collaboration empowers people across the world to find the beauty in their own ‘trash’ and pursue their dreams,” Squarespace said in a release.

This campaign follows those by other celebrities, including John Malkovich, Idris Elba and Keanu Reeves.

Squarespace: A Cautionary Tale

By Squarespace

Overall Rating 4/5

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Squarespace Advertising Sesame Street

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