Who is the guy in the Squarespace commercial?
Unmasking the man delivering websites like newspapers in the Super Bowl ad
(By Carmichael Phillip)
Introduction: A Whimsical Delivery with Irish Charm
At Super Bowl LIX, Squarespace aired its 11th blockbuster advertisement titled “A Tale As Old As Websites,” portraying a surreal send-off to the idea that the company has existed for centuries. In the spot, a modern-day website creator plays the role of an old-timey delivery boy—riding a donkey through the rolling Irish countryside and handing out laptops like newspapers to small business owners, inviting them to go online. That charismatic delivery boy is none other than Irish actor Barry Keoghan.
Meet the Actor: Barry Keoghan
Barry Keoghan, an acclaimed Irish actor known for his intense, often haunting performances, takes on a surprisingly lighthearted role in this Squarespace ad. He’s depicted as a whimsical courier delivering websites instead of newspapers, infusing the campaign with both humor and a touch of cinematic flair.
Behind the Scenes: Don Mosley and the Irish Landscape
Keoghan’s co-star is an adorable donkey named Don Mosley. The duo appears in a short companion film titled “Barry and Mosley,” in which the pair—inside a charming Irish cottage—sit down to design a website for Don using Squarespace. It’s a simple yet memorable narrative that double-dips in humor and heart, bridging the ad’s themes of accessibility and whimsy.
Artistic Vision: Storytelling Meets Brand Legacy
Directed by the creative team at Squarespace and led by the group creative director Mathieu Zarbatany, the ad seeks to humorously recontextualize the brand’s identity—imagining a world where websites have always existed, delivered like newspapers. From the tongue-in-cheek script to the lush Irish scenery, every element reinforces entrepreneurial spirit and brand heritage through cinematic storytelling.
Why It Worked: A Fan-Favorite Super Bowl Spot
Critics and viewers alike praised the ad for its balance of storytelling, charm, and nostalgia. One industry expert even called it “close to perfect,” commending the mix of humor with beautiful visual design and Keoghan’s compelling presence.
Additionally, People Magazine ran an exclusive behind-the-scenes feature describing how Keoghan reconnects with his Irish roots and donkey co-star, underscoring the authentic and playful energy of the shoot.
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