Since that fateful summer day in 2001 when the shot of Derek Watkins walking and holding an umbrella over his then boss, music impresario Sean Combs (who was transitioning to “P. Diddy” at the time), while strolling down a beach boardwalk in hot spot St. Tropez, beamed across the world, the former retail and restaurant worker’s life has never been the same. That now iconic image not only solidified Diddy’s jet-setting, international persona, but it also instantly transformed Atlanta native and Morehouse graduate Watkins into an overnight sensation. From the morning and late-night merry-go- round of Live With Regis and Kelly and The Tonight Show With Jay Leno to mainstream pubs ranging from Time to People, everyone wanted to know about the man who suddenly became Fonzworth Bentley. No longer Diddy’s valet and personal assistant, he was now an arbiter of taste and a connoisseur of gentlemanly chic. He became a ubiquitous presence: performing with OutKast at the Grammys; starring in two MTV reality shows (Making the Band 2 and his own vehicle, From G’s to Gents); launching his own line of umbrellas; and joining the pundit circuit offering sartorial advice to the style starved. Thanks to his intriguing persona, impossible-to-deny sense of fashion and burgeoning gentleman brand, Watkins covered the very first issue of UPTOWN in the summer of 2004. Here, he riffs on the early days of fame, his growth, his recent work with Kanye and how UPTOWN changed his life.
How did you find out you were chosen for UPTOWN’s first cover?
I received a call from the late and great David Watkins [the events and marketing guru, no relation, that helped launch UPTOWN, Vibe and The Source] who informed me that I was selected to be on the first cover. I was floored.
What was the response from those around you, including Diddy? Did the cover help your career at all?
My friends were elated and celebrated with me. My haters had more reasons to hate! But seriously, people really began to see who I was and appreciate the gentlemen’s movement that I was passionate about. Diddy is always happy for me! And yes, the cover really helped my career. It completely validated my brand and gave credibility to my mission of bringing class and gentleman sophistication to hip-hop.
What do you think about UPTOWN’s evolution?
It’s hard to believe that it’s been 10 years since the first issue. Magazines come and go. And, for UPTOWN to still be here and weather the downturn of the economy and other factors, proves just how relevant and necessary this voice is to our culture. I am so proud of the dedication and commitment of the hardworking staff and how each issue continues to inform and capture the “right now” of our time.
So what about your own evolution? What were you doing at the time you were on the cover? And what are you doing now?
At that time, in 2004, I was a correspondent for Access Hollywood. But, I was still trying to figure it out. I was being pulled in all kinds of directions, and had many opportunities and was having a lot of fun. As for right now, I recently signed on as the new host of BET’s Lift Every Voice, which comes on every Sunday at 10 a.m. Musically, I wrote on four songs on Kanye West’s Yeezus album, and I continue to work on my own projects. Educationally, I’m a cohost with Ledisi on the UNCF Empower Me tour, and I continue to lecture on college campuses with my New York Times best-selling book, Advance Your Swagger: How to Use Manners, Confidence, and Style to Get Ahead.
How have you grown?
First and foremost, I’m now a husband to my beautiful wife, actress Faune Chambers Watkins, and the father of our daughter, Zoie Alecia Watkins [born July 30, 2013]. These two major events have transformed, blessed and enhanced my life spiritually, emotionally and economically.
What’s in the future for Derek “Fonzworth Bentley” Watkins?
To become an international multimedia conglomerate in music, television, film and fashion. I’m just getting started!