Barry and Mosley | 2025 | Squarespace - Ad Analysis
AI Editor notes
Straight from the gut!!
“It's a classic Squarespace Super Bowl play: high-concept, cinematic, and built around a quirky star. Barry Keoghan and a donkey is a memorable combination. The ad is charming and gets the 'easy-to-use' point across well. But at nearly two minutes, it's a long walk for a simple joke. It lives or dies on Keoghan's charisma, which thankfully, is more than enough to carry it.”
Quick Summary
This ad demonstrates that Squarespace is so intuitive and powerful that you can use it to turn anyone—or anything, even a donkey—into a legitimate, bookable professional. It cleverly embeds a product demo inside a charming, absurd story, reinforcing the brand's core message that a website is the first step to making any dream real.
Executive Summary
Squarespace continues its long-running strategy of using high-concept, celebrity-driven storytelling with 'Barry and Mosley.' This piece is less of an ad and more of a short film that functions as an extended, charming product demonstration. By placing a globally recognized actor, Barry Keoghan, in an absurdly mundane situation—building a website for his donkey—the brand strips away the technical intimidation of its product and reframes it as a simple, creative act.
The core insight is powerful: legitimacy begins with a website. In the digital age, having a professional online presence is the first step to turning a hobby, a passion, or even a joke into a real venture. The ad brings this to life by treating the donkey's acting career with complete seriousness. This humorous juxtaposition is the engine of the entire spot. The execution follows a classic Setup-Turn-Payoff structure. The setup establishes the bizarre premise: Don Mosley the donkey is a 'Big Game Commercial Star'. The turn happens when Keoghan identifies the business need: 'Have you got a website?'. This seamlessly pivots the narrative into a showcase of the Squarespace platform. The payoff is the completed, professional-looking website, which validates the entire absurd endeavor, capped by the fitting tagline, 'A website makes it real.'
What makes this effective is the confidence of the execution. The creative team, working in-house, trusts the viewer to connect the dots. [5, 7, 8] They don't over-explain the features but show them in use: searching for a domain, choosing a color palette, and writing a bio. The cinematic direction by Steve Rogers, with its moody Irish setting, elevates the piece beyond a typical commercial, making it feel more like a piece of entertainment that you happen to be watching on the brand's dime. This aligns perfectly with Squarespace’s market position as the platform for discerning creatives. It’s a well-crafted piece of brand-building that entertains first and sells second, confident that the former will achieve the latter.
Theme Keywords
Brand Position
The all-in-one platform for creatives to build a beautiful and professional online presence that makes any idea real.
Brand Archetype
The Creator
Creative Game Plan
Demonstrate the simplicity and creative power of Squarespace by showing a famous actor earnestly completing the absurd task of building a professional website for his donkey.
Diagnosis: Issues & Solutions
Primary Issue: Strategic Sense
The Problem:
The ad's nearly two-minute runtime is a significant ask for viewer attention in most digital contexts outside of a captive Super Bowl audience. While effective as a long-form piece, its leisurely pace might not translate well to shorter, skippable ad formats on social media, potentially losing the core message before the payoff.
The Solution:
Develop a series of much shorter, 6-15 second cutdowns, each focused on a single, funny moment of the website-building process (e.g., just the 'donkey.actor' domain search, or the 'this is where you lie' bio moment) to ensure the humor and brand message land quickly on platforms like TikTok or Instagram Reels.