The Craft: Behind the Kid ‘n Play Progressive spot

Kid n' play
(Clockwise: Megan Steidl, Walt Geer, Roy Milton)

Since its premiere in late November, Progressive Insurance’s “Replay” featuring Kid ‘n Play, the iconic 90s hip-hop duo, has had a chokehold on consumers and audiences.

Starring Christopher Reid and Christopher Martin, the commercial, created by VML, brings the duo together for a football watch party, injecting humor and nostalgia into the scene. The insanely fun plot revolves around a misunderstanding between the two friends, leading to the need for a Replay challenge flag.

The spot, directed by O Positive’s Thaddeus McCants, seamlessly incorporates iconic nods to hip-hop culture, including the revival of the Kick Step with actress Ashley Everett and an exclusive track from the trending hip-hop duo Flyana Boss. Watch below:



Reel 360 News had a chance to chop it up with some of the brains behind the spot and we took the opportunity. We spoke with Walter Geer, Chief Creative Officer, Innovation North America, Roy Milton, Creative Director and Megan Steidl, Group Creative Director

Can you walk us through the creative concept?

Walter: Oftentimes, brands want to tap into culture, and doing so is not as easy as placing a few people of the moment into an ad. It’s a delicate dance that can be beautiful if everything from who the celebrity is and what the brand stands for, aligns. Before explaining the concept, we’d have to start with how it came about.

While boarding a flight in Houston to head back home to New York, I just so happened to see one of my childhood idols; PLAY, from Kid ‘n Play. I was FLOORED. Gave him a fist bump and a head nod like any excited fan would, and as I looked to his side, to my surprise, there was Kid…for which I had stated…”YOOOO!!” Excited and fanning out, I texted a friend, MC Serch to let him know about the experience, and his response was simple…”say wassup…those are my boys, they are nice as hell!”

When exiting the plane at LGA (LaGuardia), and after much debate with myself, I decided to introduce myself and express my interest in finding a way to work with them. Play’s response was what ignited the entire idea…”For all of these years, you know it blows my mind that with the movie we did (House Party), we never did a commercial with an insurance company f-cking up a house!”  LIGHT BULB MOMENT!

The very next morning, I called up Roy Milton (VML Creative Director) and we wrote a script that we presented to Play 48 hours later. He loved it.

So the concept is a simple one…what if Progressive tapped into the Black community and nostalgia at the same time, and created one of the most epic watch parties that completely got out of hand. Of course, Progressive will always be there to have you covered!

How did you approach blending humor and nostalgia in the commercial to resonate with both new and old audiences?

Megan: It was definitely a challenge to find the right balance. We wanted to make sure that we were able speak to new audiences while still paying homage to these hip-hop icons that older audiences know and love. We knew that we had to have a kick-step moment and a nod to Kid’s iconic flat top. For the kick step, we thought we could put a twist on it to speak to newer audiences.

We had Beyoncé’s former dance captain, Ashley Everett, dance with someone in a tiger mascot costume. For the flat top, we made a 20 ft. topiary that someone crashes into at the end of the spot. (We also took loooooots of pictures with that). To make sure that we weren’t ignoring newer audiences, we had Flyana Boss make a custom track for the spot.

They were blowing up all over TikTok at the time so we knew that would bring some new school hip-hop to the project so that we could strike just the right balance.

What were some of the challenges you encountered during the production?

Roy: We faced what seemed like endless challenges for months. Over 150 different scripts were written. We endured celebrity talent approvals for brand safety, budget challenges, hours of legal calls (both internal and from a third party) from Warner Bros. for using the likeness of Kid ‘n Play and House Party, timing and production logistics, and even cross-collaboration with agency partners.

Having Flyana Boss create a custom track for the work was nothing short of a miracle. And we got lucky featuring Ashley Everett, because Walt called her up and asked a favor when she’d already scheduled a trip that she willingly postponed to be in our campaign.

Did any of the creative team try the iconic Kid ‘n Play Kick Step on set? 

Megan: Oh yeah. We were all doing the Kick Step on set. It was a little nerve-wracking to attempt right in front of the professionals since Kid ‘n Play were right there, but they even joined in and did the Kick Step too. Talk about a dream come true – Being on set and seeing two hip-hop legends do their signature move right in front of you. Definitely surreal.

How did you ensure that the commercial effectively communicated Progressive’s message while also highlighting Kid ‘n Play’s personalities? 

Roy: Growing up as a 80’s kid, we knew we had to pay homage and salute the legacy of hip-hop and Kid ‘n Play, but we also had to evolve the story in a way that made sense for Progressive and connect today’s football fan too. So, it made sense that Kid ‘n Play are now grown men with assets to protect and insure with the brand. When we crafted the idea, we asked, “what would it have looked like if they threw another house party, but today?”

Can you share any behind-the-scenes anecdotes or memorable moments?

Roy: One moment I will always remember… watching Kid ‘n Play do their iconic dance feet away from me. My 9-year-old self was shouting inside-flashing back to sweating in my parents’ living room trying to rehearse the kick step from their music video.

Megan: Same here. Seeing Kid ‘n Play do the entire kick step when I was standing RIGHT THERE. I couldn’t believe it. It was seriously like I was in a dream. Also, hanging with Kid, Play, and Ashley while on set was great. Play sat with us in video village and laughed at the takes we were getting, just chatting throughout the day. And when we wrapped, having a dance party and dancing with Ashley Everett is definitely something I still brag about. –

What do you hope viewers take away?

Roy: We hope that it resonates with audiences young and old(er) who understand the intersection and influence of hip-hop, dance,  social media and film today. And hopefully people catch the little sprinkles of easter eggs along the way.

How has the reception been? 

Megan: I think the biggest unexpected moment was when the spot aired during the Super Bowl. Only one other time in history did the Super Bowl go into overtime, so our clients took a big risk in buying the first overtime slot, if it even happened at all. When it did, we all flipped. We were texting and screaming and celebrating. Such a huge moment that we’ll never forget.

We don’t have official numbers yet, but we definitely saw overwhelming responses across social channels and everyone posting about how Progressive got Kid and Play to be in a commercial. Plus with it being the 50th anniversary of hip hop, that only added to the celebration of this iconic duo.

An unexpected reaction is that when I went home for the holidays and told my 70-year-old uncle that I made that spot, he proceeded to recite the entire commercial to me, including understanding the flat top reference at the very end. He couldn’t believe that I made it. I couldn’t believe that he understood every single hip hop reference.

Progressive: “Replay” Season 2 resonated with target multicultural audiences including Black, Hispanic, and Asian groups. The “Watch Party” commercial connected with a wide variety of viewers on a cultural level, and we saw positive engagement across social platforms.

What do you believe contributed to its success?

Roy: I think we set out from the beginning to make something that was a part of all of us. It was Hip Hop’s 50th Anniversary year, so we had to do it right. We methodically made sure it felt true to hip hop and black film, but also that felt real to the stage of live Kid ‘n Play are in now.

That was a magical moment for us and the brand in how everything fell into place in the end. From the wardrobe, the talent choices, the music, the iconic dance, and even down to the art featured on the walls were from black artists. And the icing on the cake? We discovered during the bidding process the talented editor we all liked and selected for post-production just happened to be Play’s niece (shoutout to Quincy!).

Progressive: The concept for “Watch Party” is rooted in the campaign’s insight. Leaning into cultural moments and recognizing the importance of leveraging iconic artists as well as those resonating with viewers of today, relatability and representation were at the forefront of our strategy. We believe the blending of past and present hip-hop elements helped create relevancy amongst multigenerational audiences.  

So, who’s next? Reverend Run and Donald Mac (Run-DMC)?, Rob Bass? Doug E. Fresh? EPMD? Beasties?

Megan: You never know. We’re always down to invite more people to the party.

Progressive: These are all wonderful, talented, accomplished artists and while we don’t have anything in the works right now, you never know who the stars of our next campaign might be. 


Follow us on Facebook and Instagram


This image has an empty alt attribute; its file name is Costello_Colin-e1577461259599.jpg

Colin Costello is the West Coast Editor of Reel 360. Contact him at colin@reel360.com or follow him on X at @colinthewriter1

Kid n' play
(Clockwise: Megan Steidl, Walt Geer, Roy Milton)

Since its premiere in late November, Progressive Insurance’s “Replay” featuring Kid ‘n Play, the iconic 90s hip-hop duo, has had a chokehold on consumers and audiences.

Starring Christopher Reid and Christopher Martin, the commercial, created by VML, brings the duo together for a football watch party, injecting humor and nostalgia into the scene. The insanely fun plot revolves around a misunderstanding between the two friends, leading to the need for a Replay challenge flag.

The spot, directed by O Positive’s Thaddeus McCants, seamlessly incorporates iconic nods to hip-hop culture, including the revival of the Kick Step with actress Ashley Everett and an exclusive track from the trending hip-hop duo Flyana Boss. Watch below:



Reel 360 News had a chance to chop it up with some of the brains behind the spot and we took the opportunity. We spoke with Walter Geer, Chief Creative Officer, Innovation North America, Roy Milton, Creative Director and Megan Steidl, Group Creative Director

Can you walk us through the creative concept?

Walter: Oftentimes, brands want to tap into culture, and doing so is not as easy as placing a few people of the moment into an ad. It’s a delicate dance that can be beautiful if everything from who the celebrity is and what the brand stands for, aligns. Before explaining the concept, we’d have to start with how it came about.

While boarding a flight in Houston to head back home to New York, I just so happened to see one of my childhood idols; PLAY, from Kid ‘n Play. I was FLOORED. Gave him a fist bump and a head nod like any excited fan would, and as I looked to his side, to my surprise, there was Kid…for which I had stated…”YOOOO!!” Excited and fanning out, I texted a friend, MC Serch to let him know about the experience, and his response was simple…”say wassup…those are my boys, they are nice as hell!”

When exiting the plane at LGA (LaGuardia), and after much debate with myself, I decided to introduce myself and express my interest in finding a way to work with them. Play’s response was what ignited the entire idea…”For all of these years, you know it blows my mind that with the movie we did (House Party), we never did a commercial with an insurance company f-cking up a house!”  LIGHT BULB MOMENT!

The very next morning, I called up Roy Milton (VML Creative Director) and we wrote a script that we presented to Play 48 hours later. He loved it.

So the concept is a simple one…what if Progressive tapped into the Black community and nostalgia at the same time, and created one of the most epic watch parties that completely got out of hand. Of course, Progressive will always be there to have you covered!

How did you approach blending humor and nostalgia in the commercial to resonate with both new and old audiences?

Megan: It was definitely a challenge to find the right balance. We wanted to make sure that we were able speak to new audiences while still paying homage to these hip-hop icons that older audiences know and love. We knew that we had to have a kick-step moment and a nod to Kid’s iconic flat top. For the kick step, we thought we could put a twist on it to speak to newer audiences.

We had Beyoncé’s former dance captain, Ashley Everett, dance with someone in a tiger mascot costume. For the flat top, we made a 20 ft. topiary that someone crashes into at the end of the spot. (We also took loooooots of pictures with that). To make sure that we weren’t ignoring newer audiences, we had Flyana Boss make a custom track for the spot.

They were blowing up all over TikTok at the time so we knew that would bring some new school hip-hop to the project so that we could strike just the right balance.

What were some of the challenges you encountered during the production?

Roy: We faced what seemed like endless challenges for months. Over 150 different scripts were written. We endured celebrity talent approvals for brand safety, budget challenges, hours of legal calls (both internal and from a third party) from Warner Bros. for using the likeness of Kid ‘n Play and House Party, timing and production logistics, and even cross-collaboration with agency partners.

Having Flyana Boss create a custom track for the work was nothing short of a miracle. And we got lucky featuring Ashley Everett, because Walt called her up and asked a favor when she’d already scheduled a trip that she willingly postponed to be in our campaign.

Did any of the creative team try the iconic Kid ‘n Play Kick Step on set? 

Megan: Oh yeah. We were all doing the Kick Step on set. It was a little nerve-wracking to attempt right in front of the professionals since Kid ‘n Play were right there, but they even joined in and did the Kick Step too. Talk about a dream come true – Being on set and seeing two hip-hop legends do their signature move right in front of you. Definitely surreal.

How did you ensure that the commercial effectively communicated Progressive’s message while also highlighting Kid ‘n Play’s personalities? 

Roy: Growing up as a 80’s kid, we knew we had to pay homage and salute the legacy of hip-hop and Kid ‘n Play, but we also had to evolve the story in a way that made sense for Progressive and connect today’s football fan too. So, it made sense that Kid ‘n Play are now grown men with assets to protect and insure with the brand. When we crafted the idea, we asked, “what would it have looked like if they threw another house party, but today?”

Can you share any behind-the-scenes anecdotes or memorable moments?

Roy: One moment I will always remember… watching Kid ‘n Play do their iconic dance feet away from me. My 9-year-old self was shouting inside-flashing back to sweating in my parents’ living room trying to rehearse the kick step from their music video.

Megan: Same here. Seeing Kid ‘n Play do the entire kick step when I was standing RIGHT THERE. I couldn’t believe it. It was seriously like I was in a dream. Also, hanging with Kid, Play, and Ashley while on set was great. Play sat with us in video village and laughed at the takes we were getting, just chatting throughout the day. And when we wrapped, having a dance party and dancing with Ashley Everett is definitely something I still brag about. –

What do you hope viewers take away?

Roy: We hope that it resonates with audiences young and old(er) who understand the intersection and influence of hip-hop, dance,  social media and film today. And hopefully people catch the little sprinkles of easter eggs along the way.

How has the reception been? 

Megan: I think the biggest unexpected moment was when the spot aired during the Super Bowl. Only one other time in history did the Super Bowl go into overtime, so our clients took a big risk in buying the first overtime slot, if it even happened at all. When it did, we all flipped. We were texting and screaming and celebrating. Such a huge moment that we’ll never forget.

We don’t have official numbers yet, but we definitely saw overwhelming responses across social channels and everyone posting about how Progressive got Kid and Play to be in a commercial. Plus with it being the 50th anniversary of hip hop, that only added to the celebration of this iconic duo.

An unexpected reaction is that when I went home for the holidays and told my 70-year-old uncle that I made that spot, he proceeded to recite the entire commercial to me, including understanding the flat top reference at the very end. He couldn’t believe that I made it. I couldn’t believe that he understood every single hip hop reference.

Progressive: “Replay” Season 2 resonated with target multicultural audiences including Black, Hispanic, and Asian groups. The “Watch Party” commercial connected with a wide variety of viewers on a cultural level, and we saw positive engagement across social platforms.

What do you believe contributed to its success?

Roy: I think we set out from the beginning to make something that was a part of all of us. It was Hip Hop’s 50th Anniversary year, so we had to do it right. We methodically made sure it felt true to hip hop and black film, but also that felt real to the stage of live Kid ‘n Play are in now.

That was a magical moment for us and the brand in how everything fell into place in the end. From the wardrobe, the talent choices, the music, the iconic dance, and even down to the art featured on the walls were from black artists. And the icing on the cake? We discovered during the bidding process the talented editor we all liked and selected for post-production just happened to be Play’s niece (shoutout to Quincy!).

Progressive: The concept for “Watch Party” is rooted in the campaign’s insight. Leaning into cultural moments and recognizing the importance of leveraging iconic artists as well as those resonating with viewers of today, relatability and representation were at the forefront of our strategy. We believe the blending of past and present hip-hop elements helped create relevancy amongst multigenerational audiences.  

So, who’s next? Reverend Run and Donald Mac (Run-DMC)?, Rob Bass? Doug E. Fresh? EPMD? Beasties?

Megan: You never know. We’re always down to invite more people to the party.

Progressive: These are all wonderful, talented, accomplished artists and while we don’t have anything in the works right now, you never know who the stars of our next campaign might be. 


Follow us on Facebook and Instagram


This image has an empty alt attribute; its file name is Costello_Colin-e1577461259599.jpg

Colin Costello is the West Coast Editor of Reel 360. Contact him at colin@reel360.com or follow him on X at @colinthewriter1