Squarespace Is Going All in With a Super Bowl Ad Starring Keegan-Michael Key and Jordan Peele The website builder goes for laughs in its third spot at the big game.

By Laura Entis

Opinions expressed by Entrepreneur contributors are their own.

Squarespace

Making its third appearance, Squarespace -- which has long advertised on podcasts and in print -- is doubling down on expensive Super Bowl commercials. But it is going for something different this time around.

The New York City-based website-builder platform made its Super Bowl debut in 2013 with a relatively straight-forward 30 second ad and ran a buzzy, bizarre spot featuring actor Jeff Bridges last year that directed viewers to a microsite created for the occassion.

For 2016, it's again changing strategies. While the company is tightlipped about the specifics of its 30-second spot that will run during the big game, one thing is certain: it's going for laughs. Comedians Keegan-Michael Key and Jordan Peele, best known for their Comedy Central sketch comedy series Key & Peele, play two "ridiculous characters," says company founder and CEO Anthony Casalena. "They're two guys who pour all of their passion into a crazy idea, and use Squarespace to bring it to life."

Related: Has GoDaddy Already Won the Super Bowl?

Clearly, despite the enormous price tag -- that 30 seconds of airtime will cost around $5 million -- Casalena views the Super Bowl as a savvy investment. Last year, nearly 1 million people visited Jeff Bridge's Squarespace website as the commercial aired. It also got a burst of additional press coverage after it aired. "Jeff was promoting a movie, so he was asked about it on Jimmy Kimmel," says Casalena. "It was crazy."

While Key and Peele may not have the same name recognition as Jeff Bridges -- "Do you know them? I always have to ask!" Casalena says -- their popular sketch show proves they can generate plenty of viral, YouTube-friendly buzz.

Besides the Super Bowl, the company also plans on airing original spots at this year's Grammy and Oscar awards.

Image Credit: Squarespace

Related: During Super Bowl, the Real Action Will Be on Social Media (Infographic)

Laura Entis is a reporter for Fortune.com's Venture section.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2025.

Buying / Investing in Business

Big Investors Are Betting on This 'Unlisted' Stock

You can join them as an early-stage investor as this company disrupts a $1.3T market.

Buying / Investing in Business

From a $120M Acquisition to a $1.3T Market

Co-ownership is creating big opportunities for entrepreneurs.

Business News

AI Could Cause 99% of All Workers to Be Unemployed in the Next Five Years, Says Computer Science Professor

Professor Roman Yampolskiy predicted that artificial general intelligence would be developed and used by 2030, leading to mass automation.

Business News

Mark Zuckerberg 'Insisted' Executives Join Him For a MMA Training Session, According to Meta's Ex-President of Global Affairs

Nick Clegg, Meta's former president of global affairs, says in a new book that he once had to get on the mat with a coworker.