On the latest episode of CWTFB Radio, host Charlie MaSheen sits down with New York rapper Really Jaewon for a one-on-one conversation about his career, upbringing, and perspectives on the industry. The rapper, son of hip-hop legend Jadakiss, discusses his journey in music, his experience with podcasting, and his thoughts on the current state of NYC rap.
Jaewon, 28, shares that he grew up between two households—his mother’s home with extended family and his paternal grandmother’s house. Despite his father’s status in hip-hop, he did not grow up on tour and describes his upbringing as “regular.” He initially avoided pursuing rap but reconsidered after his freestyles gained traction. He acknowledges the challenges of being a rapper’s son, noting that nepotism is not always embraced in Black communities. Styles P was the first major figure to co-sign his music, but Jaewon remains focused on building his own name.
Beyond music, Jaewon recently worked with The Joe Budden Podcast from September to January, an experience that brought more visibility to his work. He is considering launching his own podcast under Budden’s network. On the industry side, he shares his views on the evolution of hip-hop, particularly in New York, and is critical of drill rap, especially in Boston. He also weighs in on ongoing discussions surrounding Drake’s lawsuit against Universal Music Group and controversies involving Diddy.
Jaewon also names his top five rappers, listing Jay-Z, J. Cole, Nas, The Notorious B.I.G., and Sean Carter. Looking ahead, he announces three upcoming projects: You’re Welcome, executive produced by Capella Gray, The North Star, his own solo project, and Really Violating, a collaboration with Dizzy Banko.
