A behind-the-scenes look at how that Key and Peele four-hour improv came to be

As the Chief Creative Officer of Squarespace, David Lee leads the company’s creative team, whose work encapsulates all brand creative, brand design and product design efforts for the company.

Since joining Squarespace in 2013, Lee has masterminded two Super Bowl commercials, including 2015’s Dreaming With Jeff campaign, featuring Jeff Bridges.

Most recently, Squarespace recruited the comedic powers of duo Key and Peele for an ad campaign that’s bold in execution but perhaps a bit lacking in details, given that its protagonists didn’t have the rights to directly provide live commentary on Super Bowl 50. Trademark limits forced them to to creatively skirt around team names and on-screen happenings. It was a highly popular affair, and an ambitious execution in the spirit of Squarespace’s broader You Should mantra.

PSFK had an opportunity to chat with Lee on the inspiration and trials and tribulations behind the improvised Key and Peele Super Bowl spot:

Why were Key and Peele prime spokespeople for this Super Bowl project?

We are always looking to find genuine and authentic personalities to collaborate with — it’s really important to find people who share the same creative vision as Squarespace.

The Super Bowl serves as a huge megaphone for our brand voice, and ultimately we’re looking to work with creative risk takers who not only understand what we’re about, but are also looking to do something unexpected in order to cut through the noise. This is a very intense creative process and we’re looking for people who are as passionate as we are.

With Jordan Peele and Keegan-Michael Key, we found two individuals who not only fit our core brand values, but are also creatively invested in the project. These guys are comedic geniuses with unparalleled attention to detail, and this idea wouldn’t have worked with anyone else, which is a great sign that you have something unique and original.

Any fun anecdotes on how the duo responded to the campaign?

We like to tailor ideas based on the personalities we work with, and in this case, there was always one big concept that we wanted to explore with Keegan and Jordan. Everyone agreed that the opportunity to do a live comedic improv broadcast on Squarespace could be huge. It was the riskiest idea on the table, but once we all talked about it, there really wasn’t a second option — everyone wanted to make this happen. We had some doubts, but all of those faded away once we began having conversations with Keegan and Jordan.

Every call felt like a spontaneous improv sketch, and we knew if anyone could pull off a four-hour live performance and not run out of fuel, it would be these two.

Why was now the time for Squarespace to go for this type of Super Bowl spot?

This is our third trip to the Super Bowl and we’ve learned a lot from our two previous appearances. I think the main takeaway is that in order to make an impression, you have to be brave and take some calculated risks. No one wants to make an investment this big only to be forgotten — it’s simply too grand a stage to play it safe and risk fading to the background. The Super Bowl is about more than just football — rather, it’s a moment in time that transcends different groups and interests. It’s also the only time where ads genuinely have the opportunity to be part of the entertainment. This creates a phenomenal opportunity for us to get creative with our ideas and communicate our brand message on one of the world’s biggest stages.

How did the idea for “not having rights to broadcast” become the central idea of Real Talk?

We always knew that there were some legal hurdles to overcome with this idea, but we didn’t anticipate the amount of hoops we had to jump through in order to get clearance from the network and the NFL. All the roadblocks that Key and Peele’s characters, Lee and Morris, face during the live stream are actual hurdles that Squarespace has had to overcome as well. Once we realized that that we couldn’t say player names, team names, or any specific terms related to the Super Bowl, we decided to use these legal issues as creative fuel. We made these ‘complications’ part of the narrative, turning them into an integral part of the idea. In the end, it’s actually these perceived obstacles that we feel brought the right level of tension to the campaign and ultimately highlights the creative nature of what we’re trying to do.

Squarespace Real Talk

Originally published at www.psfk.com on February 8, 2016.