Born in The Bronx and raised in Philadelphia, Set Free Richardson’s reputation as a creative mastermind has placed him as an expert on the intersection of art, music, fashion, sports, and everything cool. Besides making the AND1 Mixtapes a global phenomenon alongside co-directing and producing the "30 for 30," The Greatest Mixtape Ever documentary based on the storied street basketball brand, Richardson has also lent his unique style to collaborations with major brands running from Nike to EA Sports. 

His latest effort is a short documentary, 59Fifty Story, which explores the iconic New Era Cap Company and features interviews with notables, including Spike Lee, Carmelo Anthony, Jayson Tatum, DJ Clark Kent, and Kyle Schwarber. 

“I’ve been in the industry for so long and I think it’s always about the product and the brand of people,” Richardson explained to BET.com. “People get excited about certain brands and New Era lives in so many cultures from sports to DJing, music and acting. Everybody’s in the film are relationships I have so it was just really a good marriage of the relationships and people being excited about telling their history of the 59Fifty cap or how they’ve seen it grow through the years.”

Known for his ability to weave compelling narratives within tight timeframes, Richardson has yet again demonstrated his skills in capturing the essence of such a cultural sensation in a concise yet impactful 15-minute documentary. That doesn’t mean there weren’t any challenges in telling the decades-long story of the headwear company founded by Ehrhardt Koch in 1920 in such a tight length. 

“Less time is more trouble,” Richardson explained to BET.com. I especially have so much great cutting room floor footage with Lee and Tatum. It was tough to get it to 15 minutes, but I kind of have this format. It’s been working for me with doing all these documentaries lately, but it’s always a challenge when there's less time.” 

59Fifty Story does a fantastic job of explaining how the iconic baseball hat symbolized hometown pride and hip-hop culture in addition to stories of some of its famous wearers. Known for making baseball hats, Koch’s son Harold modernized and redesigned the company’s fitted pro cap under his leadership in 1954. Naming it the 59Fifty or the “Brooklyn Style” cap, it evolved into one of the most recognizable headwear globally, producing more than 35 million caps per year. 

One of the documentary's standout stories involves the legendary filmmaker Spike Lee. Lee's influence on the New Era brand is profound, particularly his request for a red Yankees cap, which catalyzed the expansion of New Era's color offerings. Richardson emphasizes the broader impact of this moment, noting how it paved the way for teams across various sports to experiment with different colors and designs, allowing for more personalized and symbolic representations. This change influenced baseball and permeated other sports, including basketball, football, and beyond.

“It was the most amazing thing to have him[Spike Lee] in the film but to know that he’s the reason that all New Era hats and team hats come in other colors,” Richardson said. “We never understood the power that one hat being turned red had on the culture now. That Yankee hat opened up all these different lanes for teams to do different colors and be able to do different symbolisms and meanings.”

The documentary also emphasizes hip-hop's pivotal role in popularizing New Era caps. Richardson explains that while baseball might not have been the primary sport in urban communities, the caps became a badge of identity and pride within hip-hop culture. 

From Ice Cube's Sox hat to Jay Z's Yankees cap, these hats transcended sports to become emblematic of cities and personal style. This crossover appeal extended globally, with New Era caps spotted in places like South Africa and Hong Kong, symbolizing a blend of local pride and global fashion.

A unique feature of Richardson's documentaries is the incorporation of animated segments. For example, in the segment where Spike explains the colorway change, it is done in a cool stylized animation. In 59Fifty Story, these animations fill in historical gaps where footage is unavailable or where key figures are no longer alive to share their stories. 

“I always feel like you can always fill a story up with good animation and I just wanted to pick a different style that was leaning toward the newspaper style from back in the day,” explained Richardson. “I gave it a sixties and seventies comic book style. It gave me a chance to do those stories and it played out really well.”

When Richardson isn’t providing insightful documentaries like 59Fifty Story or the Cannes Corporate TV & Media Award-winning Clarks and New York: Soles of the City, which highlights the history of the Wallabee shoes, he’s continuing to collaborate with brands like Coors Light and Listerine while moving forward with other initiatives. This includes his vision for rebranding his New York-based Compound Gallery as the Compound Art and Sound Gallery when it opens in September. 

“The first gallery was just more for different art mediums of paintings, sculptures and photography,” Richardson said. “Why is visual art and sound separated such as how music is used in horror movies like Jaws and Friday the 13th. If you take the music out of films, the art wouldn’t be the same. So this time, it’ll have a Japanese-style listening bar in it. So being able to really curate an art show with the right music, the right sound, and also doing sound art shows.”

Watch the 59Fifty Story here.