The Super Bowl is not just a game it’s advertising’s biggest show. Every year brands go all-in to capture attention, spark conversation and sometimes take brave creative risks that redefine what marketing can be. This year, we saw brands embracing celebrity, choosing unexpected narratives, irreverent humor, and strategic risk-taking to try to break through the noise.
Our strategy and creative team gathered their top picks from all the big game ads to see who had the bravest creative ideas. From Squarespace’s cinematic folklore to Homes.com’s legally defiant stunt, these were the ads that made us lean in, laugh, and think.
Let’s break down the boldest plays from this year’s Super Bowl and why they deserve a moment in the spotlight.
Jeremy: Founder & Managing Partner
Squarespace: A Tale As Old As Websites
Why’d I pick it?
I chose Squarespace’s Super Bowl ad, A Tale As Old As Websites, for its unique approach to storytelling in the tech space. Featuring Barry Keoghan in a whimsical, old-timey rural Irish setting, the ad blurs the line between old-fashioned values and today’s online culture, humorously depicting website creation as a door-to-door service in a setting that is likely internet-challenged. This fusion of imagery of a historical countryside village with modern web-building technology is both unexpected and daring.
Why is it brave?
The bravery in this work lies in its creative risk-taking. Rather than relying on typical tech tropes or showcasing product features, Squarespace leans into an imaginative, cinematic narrative that trusts the audience to connect the dots. It challenges the conventional expectation that tech ads must be sleek, futuristic, or overtly product-focused. Instead, it highlights the brand’s core message—that anyone can bring ideas to life online—through its bold metaphor.
Additionally, the ad’s humor and cultural specificity, set against an Irish backdrop with Keoghan, a rising actor, add a distinct flavor that differentiates Squarespace from its competitors. By embracing quirky, unconventional narratives, Squarespace again demonstrates that bravery in advertising isn’t just about being loud or controversial—it’s about pushing creative boundaries while staying true to their brand’s identity.
Karrie: Executive Creative Director
Pringles & Little Caesars
Why’d I pick it?
In the spirit of the event and good ol’ fashioned competition, I’m going with Nick Offerman’s Mustache vs Eugene Levy’s Eyebrows … errr Pringles vs Little Caesars. I’ll pull these apart for just a second since these brands seem to find themselves in an embarrassing coincidence?
On their part, Pringles very simply reinforces its brand mascot. Through very little overt product advertising they’re able to build affinity and recall for the package. Pulling in some big names—particularly Kansas City’s coach—puts them in the moment. I love a good humor play that grabs attention and plays with the audience.
On the other hairy facial feature, Little Caesars casts Eugene Levy’s iconic eyebrows to deliver their brand promise — so good the brows will raise right off your head. The same play, but more direct in their “whoa” message.
The best part of all this might be the follow-up from Little Caesars inviting a collab of the two brands—making the viewer wonder if it was all part of the plan. Whether or not the mashup happens is a wait-and-see. But how smart to capitalize on a moment that no one saw coming? Well played.
Why are these brave?
Well, any time you pair food with body hair — ewww. But here you have two memorable brands that are able to deliver on emotion vs the rationale. When you can strike the humor chord and restrain your sales message you can connect your brand on a deeper level. It’s great when brands can be playful and don’t take it so seriously. And the Super Bowl is the perfect time and place for such whimsy. Now, if the food mashup happens? Even braver.
Matt: Associate Creative Director
Homes.com
Why’d I pick it?
In our industry, pushing creative boundaries often feels like an uphill battle—especially when legal swoops in to sand down the edges. We dream big, then revise, then revise again until our bold idea is reduced to legally airtight mush. That’s why I have to hand it to Homes.com for their Super Bowl spot. They found a brilliantly cheeky loophole—just say the thing legal won’t let you say… but in a URL. Homes.comeisthebest.com (ahem, Homes.com is the best). It’s simple, effective, and just the right amount of rebellious.
Why is it brave?
Saying “we’re the best” takes guts. Saying it in front of millions of Super Bowl viewers? That takes brass ones. In a world where brands tiptoe around making absolute claims for fear of backlash, Homes.com threw caution to the wind. Whether it’s true or not almost doesn’t matter—because now, people are talking. And in advertising, attention is currency. Their ad is proof that a well-placed, legally-dodging, confidence-fueled stunt can cut through the noise and make an impact.
Alyssa: Associate Creative Director
Liquid Death: Drink at Work
Why’d I pick it?
I love how simple and cheeky this spot is. They didn’t go wild with production or celebrity just because it’s a Super Bowl spot. It’s so incredibly on brand—I can’t think of another water brand that could successfully pull this off. Even if you don’t know Liquid Death, it makes you wanna see what the heck is going on. Also, I gotta call out NYTimes’s critique, “Even with the reassurance at the end of the ad that the product is nonalcoholic, it’s still disconcerting to watch drivers and police officers chugging out of aluminum cans as if drinking on the job.” THAT’S THE JOKE, FFS.
Why is it brave?
What people find funny is SO personal. Humor is polarizing and that’s what makes it brave. Not everyone is going to laugh and it may even incite negative reactions. Is there anything braver than being okay with not being liked by everyone? And, featuring surgeons and pilots and police officers chugging from a can while lyrics sing, “Drink on the job. Everyone is drinking on the job.” That’s a pretty irreverent risk that you need to go all in on for it to be successful. Hedging or watering down the joke would have made this spot fall flat. Taking it all the way was necessary and down-right brave.
Nue: Content Creator
Hellmann’s Mayo: When Harry Met Sally
Why’d I pick it?
Amongst all of the ads that were trying to be super sentimental or over the top, this one stood out right away. Taking the famous When Harry Met Sally diner scene and turning it into a mayo ad? WILD! But somehow, it totally worked. It’s funny, random, and super nostalgic without feeling outdated. It manages to keep the vibe light and playful while giving a little nod to the original scene. One of the best parts is when Billy Crystal and Meg Ryan joke that no one remembers what happened the last time they were in the diner. WRONG! That scene will forever be burned into pop culture history! Definitely not what I expected from a mayo ad, and that’s why I loved it. 😂
Why is it brave?
Messing with something as iconic as that scene could’ve gone very wrong and that’s why I think it is brave. Fans of the movie could’ve been like, “wtf is this?!” But they leaned in and didn’t take themselves too seriously, which made it fun. Also, trying to make mayo the star of the show is kind of a genius move. Not every day you see a condiment steal the show. Lastly, ending with the tagline “It hits the spot” is the ultimate cherry on top for this spot. 🍒
John: Roger Federer & Elmo
Dream on? Or is it Dream QC?
Why’d I pick it?
In a world of testosterone-fueled GOAT, I was struck by a quieter bravery.
But brave nonetheless.
Now I know I’m not the only one – is it on or is it QC, or some penguin looking up?
on spent their multi millions, massive celebrity endorsement, and 30 seconds of glory on a simple, framed shot, addressing one critical brand challenge – just how do you say our name?
Brilliant.
Yes they’re on a self-declared mission to “ignite the human spirit through movement”. But they didn’t fall into the trap of lauding their purpose at a time when ironically the complete opposite broke through. They also understood that only the strong, the self-assured, can be self-deprecating. So a sneaker brand that has so much to prove, in a cut throat well heeled category (sorry), did it by making a joke at their own expense. And in doing so, made sure that the world knows their name and their self belief.
Those are our picks!
Super Bowl ads are more than just big-budget spectacles, this is the moment when advertising takes the center stage in our culture. Whether through humor, nostalgia, or outright defiance, these ads got our attention. And in a world where attention is the ultimate currency, bravery is what truly pays off.
