“Just Be Cool” | The Authentic Devotion of Swamp Dogg Gets His Pool Painted

At the onset of the global pandemic in March of 2020, the bluesy, soulful funk, rhythm and blues artist Swamp Dogg released his latest album, Sorry You Couldn’t Make It. I found my way to his genre-bending music even earlier, through his popular song “Lonely,” which served as the perfect anthem for those isolating times.

Before his rebrand, musician and producer Jerry Williams had served as a background musician, producer, and songwriter. In 1970, his original stage name, “Little Jerry Williams,” was no longer serving the persona he wanted to sonically step into, and so Swamp Dogg was born. 

In their 2025 documentary Swamp Dogg Gets His Pool Painted, directors Isaac Gale and Ryan Olson allow his story to unfold naturally and comedically. With any documentary, I am always curious as to how much footage they cut, how many tidbits and soundbite gems are omitted, in order to achieve a slim but sweet 97-minute runtime. There is a home-video-esque honesty to what the audience experiences here; the authenticity of Swamp Dogg’s devotion to his craft is the most obvious message of the movie.

Gale, in a recent interview with the Chicago Critics’ Film Festival, shared that one inspiration for the film stems back to shooting the music video for “Lonely” with Swamp Dogg. To no one’s surprise at all, the music that decorates the in-between moments of Swamp Dogg Gets His Pool Painted is one of the best aspects of the film. There’s a magnificent, magical feeling anytime a movie truly captures another creative medium. More specifically, when music is a film’s focus—whether through the score, soundtrack, or the main subject—there’s a transcendent essence distilled on screen.

As contemporary artists continue to shift towards being interdisciplinary multi-hyphenates, Swamp Dogg is a pioneer of shapeshifting through the industry. In some ways, this pattern of shapeshifting is a foolproof mechanism for maintaining relevancy while also endlessly pursuing one’s passion. The film also features Moogstar and the late Guitar Shorty, has a brief cameo from Jackass star Johnny Knoxville, and includes a short interview with Dr. Jeri, M.D., Swamp Dogg’s daughter. While we witness glimpses of each of these respective stars, it’s evident that they all shine so brightly because of Williams’s nourishing influence. 

Towards the end of the film, there’s a trippy Scooby-Doo-esque animated sequence that enhances the rest of the documentary’s nostalgic qualities. In the age of unoriginal intellectual property, many studios look to nostalgia as a saving grace of sorts. Swamp Dogg Gets His Pool Painted, while reflecting on pieces of the past, also looks at how it can inform the future of artistry. No one specific label can encompass Swamp Dogg’s art; there’s a certain confidence reflected in that. He exemplifies intuitive innovation and imagination but, as he advises at the end of the film, “just be cool.”

Swamp Dogg Gets His Pool Painted screens Monday, May 5, at 4:30 p.m., at the Music Box Theatre, as part of the Chicago Critics Film Festival.

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