Art can be more than just paint and canvas. For artist Dennis Jackson, it’s also about second chances and making a difference. Known as “The Dot Man,” Dennis is using his unique dot-style art to connect with people who often get forgotten — prisoners.
And the person he’s chosen for this special artwork is none other than famous singer Jelly Roll, who also has a past connected to prison life.
Dennis is traveling across Oklahoma, allowing inmates to be part of his new portrait of Jelly Roll. The idea? Each prisoner adds six dots to the artwork. And by the end, he plans to have 500 inmates contribute to the final piece.
Who Is Dennis Jackson, The Dot Man?
Dennis Jackson is an artist who draws using a style called pointillism. This art form uses tiny dots to create a full picture. When you look closely, you see just dots. But when you step back, all those small dots blend together to form detailed and colorful images.
This method was made famous by French artists Georges Seurat and Paul Signac in the 1800s. A great example of this style is the painting “Sunday Afternoon on the Island of La Grande Jatte” by Seurat, which even appears in the classic movie Ferris Bueller’s Day Off.
Dennis has taken this historic style and added his own twist — including people from all walks of life in his work, especially those who are often left out of creative projects, like prisoners.
What Is the Jelly Roll Portrait Project?
Dennis Jackson’s latest project is a portrait of country and hip-hop singer Jelly Roll, whose real name is Jason DeFord. Before becoming famous, Jelly Roll spent years in and out of prison for serious charges like drug dealing and robbery. But he turned his life around through music.
Now, Jelly Roll gives back by visiting prisons across America. At nearly every stop on his music tour, he visits a local prison to talk to inmates and encourage them to change their lives too.
Inspired by Jelly Roll’s story, Dennis wanted to create a portrait that reflects this message of hope and second chances. That’s why he’s letting Oklahoma inmates help him — each one adds six dots to the piece.
Where Is the Project Happening?
The project is being carried out across multiple prisons in Oklahoma. Recently, the Oklahoma Department of Corrections shared a video showing inmates at the Mabel Bassett Correctional Center in McLoud, Oklahoma adding their dots to the portrait.
Dennis hopes that 500 prisoners will take part before the project is finished. His plan is to complete the portrait by spring 2026 and present it to Jelly Roll as a gift.
Why This Project Matters
This isn’t just about art — it’s about giving hope. Involving prisoners in something meaningful shows them they can still be part of something beautiful, even while behind bars.
And by choosing someone like Jelly Roll, who has been through tough times and come out stronger, the project sends a powerful message: your past doesn’t have to define your future.