Reginald VelJohnson Who Played Carl Winslow In 90s Sitcom “Family Matters” Allegedly Had Physical Relations With Diddy

Fans have raised question about VelJohnson's sexuality!

The wild allegation comes from a podcaster who allegedly saw them together at one of Diddy’s infamous parties.

Key Takeaways

  • Comedian Luce Cannon claimed to have seen the beloved actor engage in physical intimacy with the disgraced rapper.
  • Reginald VelJohnson has not spoken about his sexual orientation despite rumors and speculations.
  • He has allegedly been dating Kiki Shepard since the 90s.

Reginald VelJohnson, who played Carl Winslow in the 1989 sitcom “Family Matters,” is a contestant in the current season of the dance talent show Dancing with the Stars.

Partnered with professional dancer Emma Slater, VelJohnson has left fans in awe with his amateur but wholesome performances.

However, the other reason VelJohnson is currently trending is not as wholesome.

Back in April 2024, comedian Luce Cannon on the Drinx with Ginx podcast claimed to have caught VelJohnson having intimate relations with disgraced rapper/producer Sean “Diddy” Combs during one of his infamous parties.

While many viewers took the claim at face value, others were skeptical. The rumor was reported by multiple hip-hop media outlets and reposted on Instagram by rapper 50 Cent.

Also, during that time, a screenshot of a tweet purportedly from Entertainment Tonight was floating around, claiming to have interviewed Reginald about his associations with Diddy.

This tweet was proven to have been photoshopped.

No further information or evidence has come out supporting this wild allegation.

VelJohnson has not spoken much about his personal life besides the rare glimpses he shares with the media, which is why rumors surrounding his sexuality cannot be substantiated.

Besides the wild claim of him being involved with Diddy, much of the speculation lies in the fact that he is unmarried and has never officially declared to have a girlfriend.

According to some sources, he is supposedly involved with “Showtime at the Apollo” host Kiki Shepard since the 90s.

Kiki Shepard and Reginald VelJohnson have both attended events together, including the 23rd Family Film Awards in 2019 and the 24th Annual NAACP Image Awards. 

In 2012, the pair attended an event for the “Marcus B. Caribbean Comedy Series,” where myKEEtv.com Caribbean Talent Network interviewed them.

In the video, Kiki can be seen holding Reginald’s arm and intimately caressing his hand.

However, this does not explicitly hint that the pair are involved romantically. Neither VelJohnson nor Kiki have spoken publicly about the nature of their relationship.

They also appeared in the 2005 short film “Sunday Evening Haircut,” written by VelJohnson himself.

Reginald VelJohnson is best known in Hollywood for playing police characters. Besides “Family Matters,” VelJohnson is best known for his portrayal of Sergeant Al Powell in the cult classics “Die Hard” and “Die Hard 2.”

He was born on August 16, 1952, in Queens, New York, to his parents, Eva and Dan. However, Dan left the family when Reginald was 13, leaving Eva to singlehandedly raise him and his brother, Barry.

After graduating from Benjamin N. Cardozo High School, he went on to pursue a Bachelor of Fine Arts from New York University.

While in college, Reginald worked with Joseph Papp’s Black/Hispanic Shakespeare Company alongside actors like Morgan Freeman and Carol Christine Hilaria Pounder.

He changed his name from the last name from Johnson to VelJohnson in order to stand out and have a name people would remember.

Who was your favorite sitcom dad? For me it was Carl Winslow from Family Matters.
byu/AdSpecialist6598 innostalgia

Despite the recent unsubstantiated rumors about VelJohnson, he is undoubtedly a beloved figure in Hollywood, especially among the fans of “Family Matters” and the “Die Hard” franchise movies.

As Diddy faces his federal charges on racketeering and s*x trafficking, the truth about the extent of his depravity will hopefully come to light.

In Case You Didn’t Know

  • Adult film star Ron Jeremy and former CIA director George Tenet were Reginald’s classmates at Benjamin N. Cardozo High School.
  • VelJohnson is also a talented pianist and had played for his school’s production of “The King and I.”

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