Who’s Your Chief Entertainment Officer?

Gap is becoming one of the most interesting brand case studies in America right now.

After taking a very public hit from the fallout of their Kanye partnership, the 57-year-old apparel company could have played it safe. Instead, it leaned harder into culture. There’s a lot marketers can learn from this moment.

Under Richard Dickson, Gap isn’t just selling hoodies again, it’s rebuilding relevance. The strategy is clear: stop acting like a traditional retailer and start behaving more like an entertainment company.

You can see it everywhere: Zac Posen is dressing Kendall Jenner in Gap at the Met Gala and music-driven campaigns with Jungle, Troye Sivan, Young Miko, and Katseye are all creating buzz. Plus, they had a standout out activation at Coachella that is replicable and scalable.

Now, Old Navy is tapping mother-daughter duo, Paris and Kathy Hilton, in a new campaign that’s already cutting through.

This isn’t doing random celebrity marketing, it’s a coordinated effort to rebuild emotional connection through storytelling, music, entertainment, and an always-on news cycle.

This week, Gap doubled down again by hiring former Paramount executive, Lourdes Arocho, as SVP & Head of Licensing to help connect the company more deeply to entertainment, sports, and the cultural moments shaping the conversation. The company is clearly working hard to build more culture capabilities in-house.

Dickson said it best this weekend in the The New York Times business section:

“Being aware of pop culture, content, art, theater, music, entertainment… you become more relevant.”

That line says it all. And, importantly, these campaigns don’t feel like traditional ads. For instance, nobody is talking about fleece pricing or denim discounts. They’re talking about the feeling, the visuals, and the soundtrack to the moment we’re in.

That’s central to Gap’s shift. The best culture marketing today doesn’t interrupt entertainment, it becomes entertainment.

Even though entertainment marketing remains harder to measure than straight performance marketing or influencer campaigns, Gap appears to be putting real frameworks in place around it. Dickson noted that the company tracks everything in real-time; from brand love to search behavior and consumer sentiment.

Ultimately, when you shift culture, business results follow. The biggest KPI is, of course, that sales are climbing. But the brand heat is climbing in kind, as are consumer conversations.

That’s not luck, that’s what happens when a company understands the modern consumer’s passion points and wants to participate in that feeling, not just advertise around it. In this environment, brands have a unique opportunity to make art rather than simply borrowing from artists. These types of orchestrations are replicable on both larger and smaller scales.

We’ve been beating this drum for a while now. Back in 2021, I told AdAge that more companies would eventually need a Chief Entertainment Officer. A few short years later, Gap is becoming one of the clearest examples of that thesis.

So don’t be surprised when more brands follow suit and begin putting their own creative spin on this. If you’re launching a new product, trying to create attention with your campaign, or trying to transform your business, leveraging entertainment marketing needs to be a big part of your marketing stack.