Ray DeJon, the legendary Brooklyn comedian and Video Music Box host, passed away at age 63 on July 14, 2025, just one day before his scheduled birthday comedy roast. The entertainment world mourns the loss of a pioneering figure who transformed New York’s comedy scene and became synonymous with hip-hop culture through his decades-long career.
The Sudden Loss of a Comedy Icon
The tragic news broke when Video Music Box founder Ralph McDaniels confirmed Ray DeJon’s passing on Instagram. “I am sad to announce the passing of our Video Music Box family @raydejon,” McDaniels wrote. “My condolences to his entire family. Ray DeJon will be missed”. The announcement sent shockwaves through the entertainment community, as many had expected to see the comedian celebrating his 64th birthday at his own comedy roast at the Brooklyn venue 275 Park Laffaholics.
Ray DeJon’s sister, Evelyn Delacruz, shared the family’s devastation on social media, writing: “I’m completely broken. Help me wish my brother Ray DeJon Jr. a Happy birthday in heaven passed 1 day before his birthday. He’s celebrating with my mom in peace on the other side. Our family is completely devastated”. The family has requested privacy during this difficult time while funeral arrangements are being finalized.
From Video Music Box to Comedy Stardom
Ray DeJon’s career trajectory exemplified the evolution of New York’s entertainment landscape. Born and raised in Brooklyn, he began his journey as a host with Video Music Box, the groundbreaking music television program that showcased hip-hop artists beginning in 1983. The show became a cultural phenomenon, and Ray DeJon played a crucial role in its success, interviewing iconic figures like The Notorious B.I.G., Stevie Wonder, and Tupac Shakur.
His transition from music television to comedy was organic. Ray DeJon discovered his comedic talents while promoting shows, leveraging his popularity from Video Music Box to sell out comedy events. “I was one of those guys that I would snap on people when I was younger,” he explained in a 2023 interview with Angela Yee. The comedian’s natural ability to connect with audiences made him a sought-after promoter and host throughout New York’s comedy scene.
Building Brooklyn’s Comedy Empire
Ray DeJon’s most significant achievement was founding Laffaholics Comedy Club, Brooklyn’s first Black-owned comedy venue. The club, located at 275 Park Avenue, became a launching pad for emerging comedians and a home for established stars. His promotional skills and industry connections helped create opportunities for countless performers, including Kevin Hart, Mike Epps, and JB Smoove, who all performed at his events during their early careers.
The comedian’s approach to comedy promotion was revolutionary. He transformed restaurants, bars, and other venues into comedy spaces, creating what he called “comedy rooms” throughout New York. “I had like a bunch of those going on,” he recalled, explaining how he gave comedians spaces to work out their material and become better performers. This grassroots approach helped establish New York as a comedy mecca.
Overcoming Personal Struggles
Ray DeJon’s life story included remarkable resilience in the face of significant health challenges. He was open about his battles with addiction and his recovery journey, which began in 1986 at a residential program called Elmcore Youth and Adult Activities. The eight-month program proved life-changing, and one counselor suggested he pursue a career in counseling, leading him to obtain his CSAC License.
His health struggles continued later in life when he suffered a stroke that left him partially paralyzed. “When I had the stroke, I had paralysis on one side and the doctors gave me the drug TPA and it worked immediately,” he explained in a 2023 interview. Ray DeJon credited his previously good health and vegetarian lifestyle for his remarkable recovery, along with his turn to herbalism for additional treatment support.
A Legacy of Laughter and Leadership
Ray DeJon’s impact extended far beyond entertainment. Holding a B.A. in human services and an internationally recognized therapist license, he dedicated significant time to speaking with youth about critical social issues including domestic violence, substance abuse, HIV/AIDS awareness, and peer pressure. His counseling background helped him develop the interviewing skills that made him such an effective host and connector of people.
The comedian’s philosophy about comedy was profound. “The art has taught me how to look outside the box to find humor in different cultures,” he shared. “I’ve learned the common denominator in humor is fun”. Ray DeJon believed that comedy could create communities of laughter across all cultures, finding midpoints that connected people regardless of their backgrounds.
The Final Days
In his final social media posts, Ray DeJon promoted his upcoming birthday roast with characteristic enthusiasm. “It’s your boy Ray DeJon the Brooklyn King of Comedy Self Proclaimed. So what? I said it,” he declared in a video post. The event was scheduled for July 16, 2025, at his beloved 275 Park venue, with fellow comedians Kenny Wu, Kenny Williams, Kay Smith, and Stephanie K set to join him on stage.
The irony of his passing just before his birthday celebration was not lost on the comedy community. Many tributes highlighted how Ray DeJon had spent his life making others laugh, only to have his own final celebration cut short by tragedy.
Industry Impact and Recognition
Ray DeJon’s influence on New York’s comedy and entertainment scene cannot be overstated. His television show “Laffaholics” aired on BRIC TV, showcasing Brooklyn’s comedy talent and culture for seven seasons. The program featured both established and emerging comedians, providing a platform for diverse voices in comedy.
His interviews with major celebrities became legendary, particularly his conversation with The Notorious B.I.G., which has been featured in three documentaries and one motion picture. Ray DeJon’s ability to make interviewees comfortable and get them to open up was a testament to his counseling background and natural charisma.
The Community’s Response
The outpouring of grief from the comedy community has been overwhelming. Comedian Jon Laster shared on Facebook how Ray DeJon had approached him early in his career, offering him $35 per weekly performance. “He was the best promoter to ever do it in NYC and I’m honored to have had a front row seat,” Laster wrote. Fellow comedian Joanna Briley noted that she had been a fan since 1987, emphasizing Ray DeJon’s role in putting New York City’s comedy scene on the map.
Bowlegged Lou from Full Force honored Ray DeJon with a special tribute, calling him “one of the gatekeepers of comedy” and praising his connection to comics throughout the city. The variety of tributes reflects the broad impact Ray DeJon had across different entertainment sectors.
Conclusion
Ray DeJon’s death represents the end of an era in New York entertainment. His journey from Video Music Box host to comedy club owner exemplified the entrepreneurial spirit that defined Brooklyn’s cultural renaissance. Through his work, he created opportunities for countless performers while maintaining his commitment to community service and youth advocacy.
The timing of his passing, just before his birthday roast, serves as a poignant reminder of life’s fragility. Ray DeJon spent his final days doing what he loved most: promoting laughter and bringing people together through comedy. His legacy lives on in the countless comedians he mentored, the audiences he entertained, and the barriers he broke as a pioneering figure in New York’s entertainment landscape.
As the comedy world processes this loss, Ray DeJon’s influence continues through the venues he created, the artists he supported, and the laughter he generated throughout his remarkable 25-year career. His story reminds us that true success is measured not just in personal achievement but in the opportunities we create for others and the joy we bring to the world.
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