The Blueprint of Pimp Hop: Inside Natalac and Lil Ru’s 20-Year Southern Hip-Hop Connection

For more than two decades, Natalac and Lil Ru have maintained a Southern hip-hop connection that stretches from Jacksonville to South Carolina, built through music, independence, entrepreneurship and years of mutual respect.

Jacksonville artist Natalac, born Sheldon Martinez Davis, and South Carolina rapper Lil Ru, born Sylvester Samuels, came from different corners of the South but developed careers that repeatedly crossed paths. A U.S. Marine Corps veteran, Natalac became known for developing his own “Pimp Hop” identity and for his 2003 record “Pimp of the City.” His larger-than-life image has also been associated with the inspiration behind A Pimp Named Slickback from Adult Swim’s The Boondocks. Lil Ru, meanwhile, built his reputation in the Carolinas before signing with Def Jam Recordings and reaching a broader audience through “The Nasty Song.”

Their connection dates back to 2003, when Lil Ru joined Natalac on “Redneckz and Kuntry Thugs,” featured on Natalac’s The Original Step Daddy. The song, which also featured Snook Da Rokkstarr and Collard Greens, brought together Florida and South Carolina influences at an early stage in both artists’ careers. More than a one-time feature, the collaboration helped establish a relationship between Natalac’s Jacksonville roots and Lil Ru’s presence in the South Carolina rap scene.

One of the most unusual connections between their careers arrived six years later. Natalac was born on August 25, 1974, and on August 25, 2009, Def Jam released Lil Ru’s debut studio album, 21 & Up. The album included “The Nasty Song,” which became one of the defining records of Lil Ru’s career. The fact that a major milestone in Lil Ru’s career landed on Natalac’s exact birthday has remained a notable part of the history the two artists share.

Photo from the music video for “Playground” by Jacksonville rapper Natalac, featuring South Carolina rapper Lil Ru.

August 25 has also grown into a much larger tradition around Natalac himself. For more than two decades, he has celebrated his birthday through events in both Jacksonville, Florida and Columbia, South Carolina, bringing together artists, collaborators and supporters from across the two regions. The events have helped strengthen the cultural connection Natalac developed with South Carolina over the years, while creating a meeting point for established names such as Lil Ru and newer artists coming through the independent Southern music circuit.

Their musical partnership returned to the spotlight in 2018 when Lil Ru appeared on “Playground,” featured on Natalac’s collaborative album Pimp of the Nation. Released through Natalac Records on February 19, 2018, the record reunited two artists who had first worked together roughly 15 years earlier. Natalac brought his familiar commanding delivery to the track while Lil Ru added the melodic presence that had helped distinguish his earlier work. An official music video accompanied the release, giving the collaboration another life beyond the album.

Natalac’s relationship with South Carolina has also been reinforced by a career that extends far beyond music. Through his freight company, Natalac Express, he has spent years traveling throughout the Southeast, frequently moving through transportation routes connecting Florida and the Carolinas, including the Interstate 95 and Interstate 26 corridors. His reputation for combining music and trucking became part of his story as he was known for driving his own 18-wheeler to performances around the country, turning his transportation business into another extension of his independent approach.

Clip from the music video for “Playground” by Jacksonville rapper Natalac, featuring South Carolina rapper Lil Ru. — Photo from the music video for “Playground” by Jacksonville rapper Natalac, featuring South Carolina rapper Lil Ru.

That independent mindset is another area where Natalac and Lil Ru share common ground. Natalac has operated Natalac Records since 1997, maintaining control of his music while developing ventures outside the entertainment industry. Lil Ru experienced the major-label system through Def Jam before eventually establishing his own imprint, Presidential Music, in 2015. Their careers offer two different perspectives on the music business, but both ultimately reflect the importance of ownership, longevity and maintaining control over a career.

From “Redneckz and Kuntry Thugs” in 2003 to “Playground” in 2018, the history between Natalac and Lil Ru extends well beyond two records. Their story connects Jacksonville and Columbia, underground Southern rap and major-label exposure, trucking and entertainment, and more than 20 years of shared history. The August 25 connection between Natalac’s birthday and the release of Lil Ru’s 21 & Up adds an unusual chapter to that story, but the real foundation remains the relationship they built long before either artist knew exactly where his career would lead.