Squarespace's 'A Tale As Old As Websites' wins a D&AD 2025 Yellow Pencil

Squarespace has run a Super Bowl ad every year since 2014, and for 2025 it treated the Big Game as more than a single broadcast. Led by chief creative officer David Lee, the in-house team wanted work that lived in the weeks around the game, so it started from an insight about the brand itself: Squarespace has existed nearly as long as websites have.

That insight became 'A Tale As Old As Websites', a mythic origin story set in a bygone Irish town where websites are delivered door-to-door like newspapers. Actor Barry Keoghan plays a whimsical, donkey-riding delivery boy who tosses laptops through windows and across fields to help local businesses get online. The 30-second spot aired between the first and second quarters of Super Bowl LIX on 9 February 2025, directed by Biscuit's Steve Rogers and shot on Ireland's western coast in December.

The writing was central from concept to final cut: storyboards leaned on narrative beats, pacing and dialogue, Keoghan improvised lines on set, and the production adopted an indie-film style of rain-soaked shoots and tight schedules. As Lee put it, 'Would it be such a bad thing if the only word the viewer understood was Squarespace?'

Around the spot, Squarespace released teasers, a short film in which Keoghan builds a website for his donkey co-star Mosley, and a dedicated Mosley website template for aspiring entrepreneurs. The campaign won a D&AD 2025 Yellow Pencil, and The One Show 2025 winners announcement credited Squarespace's New York in-house team with three Gold Pencils.